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Comprehensive Summary: Carbohelicenes have garnered considerable attention for their inherent chirality and structural flexibility. Increasing multi‐helicity and incorporating non‐six‐membered rings to substitute benzenoid rings within helicenes are effective strategies for introducing unique photoelectric properties. Despite the disclosure of numerous helicenes, the inaccessible precursors and the lack of synthetic routes pose a challenge in achieving desired helicene structures fused with non‐benzenoid rings. Herein, we report the synthesis of multiple non‐benzenoid carbohelicenes fused with fluorene unit(s) through intramolecular cyclodehydrogenation of 9,10‐di(naphthalen‐1‐ yl)anthracene on Au(111) surface. Two potential cyclodehydrogenation manners between naphthyl and anthracene lead to the formation of fluorene‐fused [5]helicene and [4]helicene moiety. Consequently, a total of four stable products were observed. The atomic topographies of products are characterized by bond‐resolving scanning tunneling microscopy. The chiral helicity of targeted products can be switched by tip manipulation. Density‐functional‐theory calculations unveils the reaction pathway of four products. The comparative analysis of their respective energy barriers exhibits a correlation with the experimentally determined yields. Furthermore, we synthesize the polymer chains incorporating non‐benzenoid carbohelicenes via the Ullmann reaction of 2,6‐dibromo‐9,10‐di(1‐naphthyl)anthracene precursors. Our work proposes a synthetic methodology for several novel helicene‐like structures fused with fluorene units and the polymer bearing helicene subunits, thus highlighting the immense potential of these compounds in the application fields of luminescent electronic devices. [ABSTRACT FROM AUTHOR]

The 1D array of electron donor–acceptor chromophoric organic molecules is of paramount importance for photovoltaic, catalytic and optoelectronic applications. Herein, we report coordination driven 1D arrays of an electron-donor guest (fluorene, carbazole, dibenzofuran, and dibenzothiophene) and o-phen chelator as an acceptor in a Zn-based porous coordination polymer, {[Zn(o-phen)(ndc)]·DMF} (PCP-1). All the guest-encapsulated PCPs were characterized by performing single-crystal structure determinations and showed emission driven by charge transfer. Exciton binding energies were calculated and correlated with electron-donating capabiliities of the guest molecules. [ABSTRACT FROM AUTHOR]

Synthesizing molecules with significant topological features, such as catenanes, tailored with specific groups to confer desired functionality, is essential for investigating various properties arising from the entanglement due to mechanical bonds. This investigation can pave the way for uncovering novel functional materials employing mechanically interlocked molecules (MIMs). In this direction, we have synthesized a π‐donor (D) and π‐acceptor (A) functionalized [2]catenane using a non‐labile Co(III) metal ion as a template with pyridine‐diamide templating center and utilizing click reaction for ring‐closing. The donor group is a fluorene derivative, and the acceptor is a benzophenazine derivative, commonly employed in synthesizing conjugated polymers for various optoelectronic devices. Synthetically, the acceptor group was introduced into a macrocycle with a pyridine diamide unit. It was then threaded with a ligand having alkyne terminals to obtain the desired [2]pseudorotaxane utilizing cobalt ion as a template. Ring‐closing was then performed with a di‐azide functionalized molecule with the donor chromophore. The desired D−A functionalized [2]catenane was obtained after demetalation. All the starting materials, macrocycle, and entangled structures have been characterized by 1H‐NMR, 13C‐NMR, and mass spectroscopy. Some of these materials were also characterized by single‐crystal X‐ray analysis. The photophysical properties are studied by UV‐visible and fluorescence spectroscopy. [ABSTRACT FROM AUTHOR]

Sequential Knoevenagel condensation/cyclization using cyclic active methylene compounds such as Meldrum's acid have been studied. The reaction of 2-(1-phenylvinyl)benzaldehyde and Meldrum's acid, dimedone, or 1,3-indandione with piperidine/AcOH or L-proline at room temperature for 17–18 h gave cyclized indene derivatives in 63–80% yield. The reaction of 2-(3,5-dimethoxyphenyl)benzaldehyde and Meldrum's acid at room temperature for 17 h gave a fluorene derivative in 98% yield. Furthermore, the reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum's acid with piperidine at room temperature for 18 h gave a dihydroanthracene derivative bearing Meldrum's acid in 83% yield. The reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum's acid with piperidine at 110 °C for 2 h gave Meldrum's acid fragmentated dihydroanthracene derivative in 48% yield. The reaction mechanisms of the cyclization steps and Meldrum's acid fragmentation have been examined by the DFT calculations. [ABSTRACT FROM AUTHOR]

Developing anion exchange membranes (AEMs) is an effective way to reduce the cost of water electrolyser systems and fuel cell systems because of the no requirement of platinum-group-metal (PGM) catalysts. However, low conductivity and poor stability are the bottlenecks that constrain its development. In this work, we propose a series of performance enhanced poly (terphenyl-co-fluorene quinuclidinium) (TPFQ) AEMs. The hydroxide conductivity of TPFQ-10 reached 178.5 mS cm−1 at 80 °C. The rigid fluorene group gives the membrane better dimensional stability (swelling ratio: 7.7% in pure water and 1.2% in 10 M NaOH at 80 °C for TPFQ-10). In particular, the membranes exhibit extremely high alkaline stability, with almost no conductivity loss over more than 2000 h in a 10 M NaOH solution. The AEM water electrolysers (AEMWEs) with nickel-alloy foam electrodes shows an excellent current density of 2.32 A cm−2 at 2.0 V. The AEMWEs can work steadily at a current density of 0.5 A cm−2 in 5 M NaOH at 80 °C for more than 500 h, with a low voltage rising rate of 56 μV h−1. • Synthesized a series of performance enhanced poly(terphenyl-co-fluorene quinuclidinium) (TPFQ) AEMs. • The AEMs have a high OH− conductivity (178.5 mS cm−1 at 80 °C), high mechanical properties (60.3 MPa TS) and excellent dimensional stability(swelling ratio: 7.7% in pure water and 1.2% in 10 M NaOH at 80 °C). • The AEMs exhibit extremely high alkaline stability, with almost no conductivity loss over more than 2000 h in a 10 M NaOH solution. • The AEMWE with nickel-alloy foam electrodes shows excellent current density (2.32 A cm−2 at 2.0 V) and high durability. [ABSTRACT FROM AUTHOR]

We report the discovery in TMC-1 of two cyano derivatives of the PAH acenaphthylene (C12H8). We have found two series of lines with the QUIJOTE line survey that we assign to 1-C12H7CN and 5-C12H7CN. For the 1-isomer, we have detected and assigned 173 rotational transitions with J up to 46 and Ka up to 9, corresponding to 107 independent frequencies. For the 5-isomer, the identification is based on 56 individual lines, corresponding to 117 rotational transitions with J up to 40 and Ka up to 8. Identification of the carriers was achieved through a careful analysis of the derived rotational constants, which permit us to focus on molecules larger than naphthalene but smaller than anthracene and phenanthrene. Moreover, the derived rotational constants indicate that the species are planar; this allows us to discard derivatives of fluorene and acenaphthene, which are non-planar species. Quantum chemical calculations and subsequent chemical synthesis of these molecules, as well as the observation of their rotational transitions in the laboratory, unequivocally support our identifications. We also confirm, via a robust line-by-line detection, the previous claimed detection of 1- and 2-cyanonaphthalene, which were obtained through statistical stacking techniques. The column densities of 1- and 5-cyanoacenaphthylene are (9.5 ± 0.9) × 1011 cm−2, while those of 1- and 2-cyanonapthalene are (5.5 ± 0.5) × 1011 cm−2. Hence, it seems that acenaphthylene could be a factor of 1.7 more abundant than naphthalene. These results support a scenario in which PAHs grow in cold dark clouds based on fused five- and six-membered carbon rings. [ABSTRACT FROM AUTHOR]

Despite the limited success of copper-catalyzed alkylations, (NNS)CuCl proved to be an effective catalyst for the sp3 C–H alkylation of fluorene with alcohols. Various primary alcohols and challenging secondary alcohols were successfully used. The practical applicability of the method was effectively tested with several post-functionalization reactions. This copper-catalyzed alkylation of fluorene involved a borrowing hydrogen mechanism. [ABSTRACT FROM AUTHOR]

Noncovalent spatial interaction has become an intriguing and important tool for constructing optoelectronic molecules. In this study, we linearly attached three conjugated units in a multi π‐stacked manner by using just one trident bridge based on indeno[2,1‐b]fluorene. To achieve this structure, we improved the synthetic approach through double C−H activation, significantly simplifying the preparation process. Due to the proximity of the C10, C11, and C12 sites in indeno[2,1‐b]fluorene, we derived two novel donor|acceptor|donor (D|A|D) type molecules, 2DMB and 2DMFB, which exhibited closely packed intramolecular stacking, enabling efficient through‐space charge transfer. This molecular construction is particularly suitable for developing high‐performance thermally activated delayed fluorescence materials. With donor(s) and acceptor(s) constrained and separated within this spatially rigid structure, elevated radiative transition rates, and high photoluminescence quantum yields were achieved. Organic light‐emitting diodes incorporating 2DMB and 2DMFB demonstrated superior efficiency, achieving maximum external quantum efficiencies of 28.6 % and 16.2 %, respectively. [ABSTRACT FROM AUTHOR]

There are many options to design a molecular structure that could result in thermally activated delayed fluorescence (TADF). One promising strategy is to use the donor‐π‐acceptor motive where an electron‐donating unit is linked to an electron‐acceptor via an aryl moiety like phenyl. While this approach is widely used and well understood, the performance of the chromophores can be limited by different energy loss pathways, e. g. internal conversion, or by π‐stacking. To circumvent these problems rigid structures with sterically demanding substituents are applied. In this work, we designed two TADF emitters based on phenothiazine and nitrile linked via spiro‐9,9’‐bi[fluorene] or 9,9‐dimethylfluorene and compared the effect of the linker on the physical properties of the dyes. This work emphasizes the importance of careful design of conjugated spacer for efficient TADF emitters. [ABSTRACT FROM AUTHOR]

Developing films of chiral metal–organic frameworks (MOFs) with high circular polarization luminescence (CPL) is facing a great challenge for chiral sensing applications. Herein, a layer‐by‐layer chiral induction method is first reported to prepare enantiopure MOF films for CPL sensing. By layer‐by‐layer induction with the chiral inductor camphorsulfonic acid, fluorene‐based chiral MOF D/L‐ZnHF‐SO2 film (HF‐SO2 = 3,7‐Dibenzothiophenedicarboxylate, 5,5‐dioxide) with preferential growth orientation and homogeneous surface are prepared, which shows strong chiral feature and CPL with higher asymmetry factor of ±0.073. In addition, by mixed ligand approach, the isostructural fluorene ligand 9‐fluororenone‐2,7‐dicarboxylate is chosen to replace part of HF‐SO2 for preparing a series of chiral MOF films with tunable CPL emission. Furthermore, the prepared chiral MOF films with strong CPL performance are further utilized for enantiomers sensing. The CPL changes consisted with enantioselective adsorption results showed that D/L‐ZnHF‐SO2 film has good discrimination against chiral R/S‐phenylethylamine enantiomers, first reporting chiral MOF‐based candidates for the application in CPL sensing of enantiomers. This work provides a facile and effective approach for preparing chiral MOF films materials with high and tunable CPL performance, and also gives a new way to achieve CPL sensing of chiral enantiomers. [ABSTRACT FROM AUTHOR]

A series of a novel CAAC ligands featuring a spiro‐fluorene group have been synthesized and complexed with ruthenium alkylidenes, yielding the corresponding Hoveyda‐type derivatives as a new family of olefin metathesis catalysts. The novel complexes have been characterized by XRD, HRMS and NMR measurements. The synthetised complexes were tested in catalysis and showed good activity in olefin metathesis, as demonstrated on diethyl diallylmalonate and allyl acetate substrates. The unique backbone in the ligand with the large, yet inflexible condensed system renders interesting properties to the catalyst, exemplified by the good catalytic performance and improved Z‐selectivity. In addition, the complex can also serve as a hydrogenation catalyst in a consecutive (one‐pot) reaction. The latter reaction can convert allyl acetate to butane‐1,4‐diol, a valuable chemical intermediate for biodegradable polybutylene succinate (PBS). [ABSTRACT FROM AUTHOR]

Comprehensive Summary To address the stereoselective synthesis challenge in π‐stacked grids with four chiral centers, we utilized coplanar and highly rigid 11,12‐dihydroindeno[2,1‐a]fluorene‐11,12‐diol and 2,2'‐bithiophene as synthons, employing Friedel‐Crafts gridization (FCG). Leveraging the supramolecular interactions of S···S and π···π within the thiophene moiety, along with the steric effect of the 11,12‐dihydroindeno[2,1‐a]fluorene scaffold, we successfully achieved the exclusive generation of a single isomer of Ladder‐type π‐stacked grids (LGs‐IF) containing six theoretical isomers. By subsequently substituting 2,2'‐bithiophene with thiophene/bithiophene derivatives as synthons, we maintained an exceptionally high level of stereoselectivity. This study introduces a novel approach for the stereo‐controlled preparation of grids involving multi‐chiral centers. [ABSTRACT FROM AUTHOR]

The title compound was synthesized from perfluoro-1-ethyltetralin and 1,2,3,4-tetrafluorobenzene under the action of antimony pentafluoride as a mixture of cis- and trans-isomers in a 71% isolated yield. The structure and cis-/trans-configuration of the isomers were determined by NMR (19F, 13C), 19F–19F COSY, and 19F–19F NOESY 2D NMR spectroscopy. [ABSTRACT FROM AUTHOR]

Multiresonance thermally activated delayed fluorescence (MR‐TADF) emitters with high color purity in virtue of their inherent narrowband emission have received great interest in organic light‐emitting diodes (OLEDs). However, it remains a big challenge to develop the ultrapure blue MR‐TADF emitters with high efficiency. In this work, a novel “dual‐MR‐core” strategy is proposed by connecting two parent N‐B‐O‐skeletons with non‐conjugate 9‐position substituted fluorene linkages for high efficient deep‐blue MR‐TADF emitters, namely H‐FOBN and Me‐FOBN, which possess the highly twisted structure with suppressed aggregation. Finally, the vacuum‐deposited deep‐blue OLED exhibits excellent external quantum efficiency (EQE) of 25.1% with small full width at half maximum (FWHM) of 28 nm, as well as CIE of (0.14, 0.08). Furthermore, owing to enhanced solubility, the solution‐processed deep‐blue OLED based on Me‐FOBN shows EQE of 11.3%, with small FWHM of 32 nm and CIE of (0.14,0.09). These outstanding performances confirm that this “dual‐MR‐core” strategy provides a feasible approach to develop high efficient ultrapure blue MR‐TADF emitters. [ABSTRACT FROM AUTHOR]

Non‐benzenoid diradicaloids possessing high‐spin ground states are attractive synthetic targets given their high potential for spintronics and quantum computing. Nevertheless, the synthesis of such compounds remains highly challenging due to their inherent instability. In this work, we present the synthetic attempt towards creating a non‐benzenoid diradicaloid (1) with a triplet ground state by fusing two cyclohepta[def]fluorene units onto a benzene ring. Our synthetic approach involves both oxidation and reduction pathways. In the oxidation path, we obtained the partially dehydrogenated products 1+H and 1+2H containing an indeno[1,2‐b]fluorene core from the tetrahydro precursor (2). However, further dehydrogenation to afford the target molecule (1) did not proceed. On the other hand, with the reduction pathway, a novel tetraketone precursor (9) with two pairs of pentagons and heptagons was successfully synthesized. The subsequent nucleophilic attack however was proved to be difficult probably due to the unselective nucleophilic addition on the zigzag nanographene ketones. Furthermore, UV‐vis absorption, cyclic voltammetry, and theoretical calculations were conducted to explore the optical, electrochemical properties, and aromaticity of all the obtained molecules (1+H, 1+2H and 9). Although the desired target 1 is not achieved, our work provides insight into designing novel high‐spin non‐benzenoid NGs based on nonalternant cyclohepta[def]fluorene system. [ABSTRACT FROM AUTHOR]

Dynamic polyimines are a class of fascinating dynamic polymers with recyclability and reparability owing to their reversible Schiff‐base reactions. However, balancing the dynamic properties and mechanical strength of dynamic polyimines presents a major challenge due to the dissociative and associative nature of the imine bonds. Herein, we introduced bulky fluorene groups and polyether amine into the skeleton of polyimine networks to achieve a tradeoff in comprehensive properties. The resulting dynamic polyimines with fluorene groups (Cardo‐DPIs) were successfully synthesized by combining the rigid diamine 9,9‐bis(4‐aminophenyl)fluorene and the flexible polyether amine, demonstrating a high tensile strength of 64.7 MPa. Additionally, Cardo‐DPIs films with more content of rigid fluorene groups exhibited higher water resistance, glass transition temperature and wear‐resisting ability. Moreover, the Cardo‐DPIs films not only efficiently underwent thermal reshaping, but also exhibited excellent self‐healing capabilities and chemical degradation in acidic solutions. Furthermore, the resulting films can achieve fully closed‐loop recovery by free amine solution for 2 h at room temperature. This study broadens the scope of dynamic polyimine materials and promotes the balanced development of their functional and mechanical properties. [ABSTRACT FROM AUTHOR]

Heterogeneous solid base catalysts have attracted widespread attention for various reactions from the perspective of green and economy chemistry due to their advantages such as low corrosiveness, high reaction efficiency, and easy separation. The unique properties of polyacrylonitrile fibers (PANF) such as good mechanical strength and a surface rich in cyanine and economy make them suitable catalytic supports. Herein, potassium oxide was introduced into PANF by redox strategy. Characterization using XRD, FT-IR, solid-state 13C NMR, XPS, SEM, CO2-TPD, etc. confirmed the successful preparation of this heterogeneous base catalyst and the participation of PANF in the redox process of KNO3 to promote the decomposition of KNO3. The acquired catalyst showed obvious activity for the oxidation of methylene compounds and the yield of fluorenones can reach 100% at 100 °C. This strategy provides a new development path for the application of PANF and the synthesis of heterogeneous bases. [ABSTRACT FROM AUTHOR]

Organic diradicaloids have lately emerged as potential spintronic materials. We report the unprecedented synthesis of a near-IR absorbing indeno[2,1-a]fluorene derivative that displays remarkably low LUMO (−4.15 eV) and a small HOMO–LUMO gap (0.85 eV). NMR/EPR studies indicated its open-shell diradical property, which was supported by DFT calculations while suggesting a 30% diradical character and a small singlet (S)–triplet (T) gap (−2.52 kcal mol−1). A large bond length alternation of the as-indacene core for its single-crystals indicated a quinoidal contribution with greater antiaromaticity, which is in line with the small diradical character despite showing a small S–T gap. [ABSTRACT FROM AUTHOR]

Oxidative stress is a trigger for many diseases and occurs with the unstable hypochlorite (ClO−), known as one of the reactive oxygen species (ROS) in organisms. Then, HOCI is acknowledged as an oxidizing species that eliminates a variety of environmental pollutants. Hence, the development of novel methodologies for the selective and precise identification of HOCl/ ClO− is considered to be of utmost importance. In this study, the design, characterization, and applications of a fluorene-based fluorescent probe (FHBP) dependent on the ESIPT mechanism with a "turn-on" response for the sensitive/selective determination of ClO− against other competing samples were reported. The experimental results indicated that the detection limit for ClO−could be quantitatively determined by the probe to be 8.2 × 10−7 M. The binding constant of the probe FHBP with ClO− was computed as 9.75 × 103 M−1. In addition, the response time of FHBP was appointed to be 30 s, indicating a rapid reaction with ClO−. It has also been demonstrated that this probe can be successfully used for the detection of ClO− on filter papers, TLC sheets, cotton swabs, and real samples. [ABSTRACT FROM AUTHOR]

Random and block polyarylates were synthesized using bisphenol A (BPA), bisphenol fluorene (BHPF), terephthaloyl chloride (TPC), and isophthaloyl chloride (IPC) as raw materials. The synthesis strategies of one-step and stepwise interfacial polymerization methods were adopted. Both types of polyarylates exhibited similar solubility, with block polyarylates showing slightly broader solvent selectivity. The presence of large sterically hindered fluorene groups in BHPF monomers rendered both block and random polyarylates amorphous by restricting the movement of macromolecular segments. The polyarylates demonstrated excellent thermal stability (T5% = around 490 °C) and a high glass transition temperature (Tg > 210 °C). As the covalent bonds of the monomer linkage showed no significant difference, the thermal stability of both types of products was similar. The glass transition temperature increased with an increase in TPC and diefluorene monomer content. The tensile strengths of the random and block polyarylate films ranged from 45.77–69.89 MPa and 49.49–55.29 MPa, respectively, indicating the high tensile strength of the resulting polyarylates. While the block polyarylates did not show significant differences from the conventional properties of random polyarylates, the synthesis of block polyarylates in this study represents a novel attempt, further highlighting the significant influence of the large pendant group of the main chain on the ordered arrangement of molecular segments. [ABSTRACT FROM AUTHOR]

A ruthenium nitrosyl complex of formula [RuII(fluorene(C6)CH2O-terpy)(bipy)(NO)]3+ (AC) in which fluorene(C6) is the 9,9-dihexylfluorene, terpy the 2,2′;6′,2′′-terpyridine, and bipy the 2,2′-bipyridine is presented with its related [RuII(MeO-terpy)(bipy)(NO)]3+ (C) and 9,9-dihexylfluorene 2-hydroxymethylfluorene (A) building blocks. The reference complex C undergoes NO release capabilities under irradiation at λ = 365 nm. The effect of the introduction of the fluorescent A antenna within the resulting AC complex is discussed both experimentally and theoretically. The importance of the encaging parameter defined as φAC·IAC, in which IAC is the quantity of light absorbed by AC and φAC the quantum yield of NO release is evidenced and found to be concentration dependent. The conditions of optimization of the antenna approach to maximize φAC·IAC are discussed. The crystal structure of [RuII(fluorene(C6)CH2O-terpy)(bipy)(NO2)](PF6), the last intermediate in the synthesis of AC is also presented. [ABSTRACT FROM AUTHOR]

This paper reports the construction of racemic and enantiopure (D‐ and L‐) fluorene and fluorenone‐based novel unnatural amino acid derivatives. The Pd(II)‐catalyzed bidentate directing group‐aided arylation of prochiral β‐C(sp3)‐H bonds in racemic, enantiopure carboxamides of amino acids with iodofluorenes was reported. The construction of novel examples of fluorene and fluorenone motifs containing amino acids comprising of norvaline, leucine, phenylalanine, norleucine, 2‐aminooctanoic acid derivatives having the anti‐stereochemistry (with good enantiopurity) was accomplished. The construction of bis fluorenyl alanine scaffolds and fluorenyl motif‐containing non‐α‐amino acid (aminoalkanoic acid) derivatives was also reported. Examples of removal of the directing group (8‐aminoquinoline) and phthalimide‐protecting group present in the fluorenyl‐based unnatural amino acid derivatives have been shown. Accordingly, fluorene motif‐based amino acid esters and free amino group‐containing unnatural amino acid derivatives were synthesized. The stereochemistry of the major (anti) diastereomers obtained via the prochiral β‐C(sp3)‐H arylation of norvaline, leucine, phenylalanine, norleucine, 2‐aminooctanoic acid derivatives was ascertained from the X‐ray structure of a representative compound. Fluorene‐ and fluorenone‐based motifs are vital skeletons in materials and medicinal chemistry research. Accordingly, this work is a contribution towards enriching the library of fluorene and fluorenone unnatural amino acid scaffolds. [ABSTRACT FROM AUTHOR]

Structurally symmetric dyes using functionalized fluorenes and benzotriazole as the main building moieties have been synthesized and found to exhibit efficient dual-state emission (DSE) and interesting two-wavelength or dual amplified spontaneous emission (dual-ASE) behaviors in the solution phase, which may benefit the development of organic gain materials with dual-wavelength amplification. [ABSTRACT FROM AUTHOR]

9,9-bis(4-hydroxyphenyl)fluorene (BPF) is a highly structurally symmetric bisphenol with excellent optical properties of low birefringence and high refractive index, however, the glass transition temperature (T g) of its polyester is high (T g>300°C), which makes it difficult to be thermally processed and limits its application. On the other hand, 4,4′-Thiobis (2-methylphenol) (T2MP) has a flexible thioether group, its introduction not only brings high refractive index, but also can appropriately reduce the T g of the polymer. Therefore, by combining the advantages of both of them, we prepared aromatic polyesters with high refractive index and stabilization. This study provides a route that can appropriately reduce T g without loss of refractive index. [ABSTRACT FROM AUTHOR]

We report six new 2,6-disubstituted fluorene-based conjugated molecules carrying orthogonal triphenylamine and pyridine moiety as donor-acceptor units at the C-9 position. The geminal donor-acceptor is connected to the fluorene core by σ-conjugation. Optical/solvatochromic studies, investigated by UV-VIS absorption and fluorescence spectroscopy, show blue emission with good quantum yield (40–70%) in solution and in thin film state for the synthesized compounds. In microsecond order, the derivatives give a shorter delayed lifetime (both in solution and thin films), facilitating reverse intersystem crossing (RISC). TD-DFT studies for all the derivatives show minimal singlet-triplet splitting in the gas phase (close to 0.2 eV), and the high thermal stability confirmed by the compound's TGA method (320–398 °C) makes them very useful in the optoelectronic market. D-σ-π-σ-A based blue emitters carrying orthogonal triphenylamine and pyridine moiety as donor-acceptor unit at C-9 position were synthesized. Optical/solvatochromic studies, investigated by UV-VIS absorption and fluorescence spectroscopy, show blue emission with good quantum yield (40–70%) in solution and in thin film state for the synthesized compounds. [ABSTRACT FROM AUTHOR]

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Smart solvatochromic isocyano-aminoarenes (ICAArs) have been gaining attention owing to their unique photophysical, antifungal and anticancer properties. Using a simple dehydration reaction with in situ-generated dichlorocarbene, we prepared 2-amino-7-isocyanofluorene (2,7-ICAF). We studied the effect of the longer polarization axis provided by the fluorene core on the spectral properties and we also compared it to those of the starting diamine. 2,7-ICAF shows a clear solvatochromic behavior close to the blue part (370–420 nm) of the visible spectrum. Quantum chemical calculations show internal charge transfer (ICT) between the donor amino and the electron-withdrawing isocyano groups. 2,7-ICAF has high molar absorptivity (ε = 15–18·103 M−1cm−1) and excellent quantum yield (Φf = 70–95%) in most solvents; however, its fluorescence is completely quenched in water. The high brightness (ε·Φf) and close to zero quantum yield in water may be favorable in biolabeling applications, where background fluorescence should be kept minimal. Overall, 2,7-ICAF shows enhanced photophysical properties compared to its previously investigated relative 4-amino-4′-isocyano-1,1′-biphenyl (4,4′-ICAB). [ABSTRACT FROM AUTHOR]

Smart solvatochromic isocyano-aminoarenes (ICAArs) have been gaining attention owing to their unique photophysical, antifungal and anticancer properties. Using a simple dehydration reaction with in situ-generated dichlorocarbene, we prepared 2-amino-7-isocyanofluorene (2,7-ICAF). We studied the effect of the longer polarization axis provided by the fluorene core on the spectral properties and we also compared it to those of the starting diamine. 2,7-ICAF shows a clear solvatochromic behavior close to the blue part (370–420 nm) of the visible spectrum. Quantum chemical calculations show internal charge transfer (ICT) between the donor amino and the electron-withdrawing isocyano groups. 2,7-ICAF has high molar absorptivity (ε = 15–18·103 M−1cm−1) and excellent quantum yield (Φf = 70–95%) in most solvents; however, its fluorescence is completely quenched in water. The high brightness (ε·Φf) and close to zero quantum yield in water may be favorable in biolabeling applications, where background fluorescence should be kept minimal. Overall, 2,7-ICAF shows enhanced photophysical properties compared to its previously investigated relative 4-amino-4′-isocyano-1,1′-biphenyl (4,4′-ICAB).

Herein we report a sustainable approach for the alkylation of ketones, 9H‐fluorene, oxindole, and indole using alcohols as the alkylating agent catalyzed by a well‐defined air‐stable zinc catalyst (1 a) of a tridentate redox non‐innocent arylazo ligand, 2‐((4‐chlorophenyl)diazenyl)‐1,10‐phenanthroline (La). 2–3 mol % of 1 a efficiently produces substituted α‐alkylated ketones, 9‐alkylated fluorenes, C3‐alkylated oxindoles, and C3‐alkylated indoles in moderate to good isolated yields. In aerial condition, the formation of bis(indolyl)methane (BIMs) derivatives were observed when indoles were subjected to alkylation by primary alcohols. A few drug molecules containing BIMs were prepared in good isolated yields. The catalyst 1 a exhibited good chemoselectivity during the functionalization of fluorene and indole with oleyl alcohol and β‐citronellol. A few control experiments, including deuterium labeling experiments, performed to unveil the reaction mechanism indicate that the one‐electron reduced azo‐anion radical species [1 a]‐formed in situ, acts as the active catalyst. All the redox events occur at the redox‐active aryl‐azo ligand, which acts as the reservoir of hydrogen and electrons throughout the catalytic cycle, keeping the Zn(II)‐center as a template. [ABSTRACT FROM AUTHOR]

9-(4-Aminophenyl)-9-(4-hydroxyphenyl)fluorene reacted with 4,4′-difluorobenzophenone to afford an aromatic ketone-containing aromatic diamine. The aromatic diamine was polymerized with four kinds of tetracarboxylic dianhydrides at room temperature(rt) followed by chemical imidization (Ac2O/NEt3) at 160 °C to afford the corresponding aromatic poly(ether ketone)-polyimide (PEK-PI) alternating copolymers. The resulting PEK-PI copolymers have sufficiently high molecular weights (Mw = 37,600–47,500 or insoluble in all organic solvents), thermal stability (Tg = 269–363 °C) above aromatic poly(ether ketone)s and below aromatic polyimides, and more colorless transparency than typical aromatic poly(ether ketone)s and aromatic polyimides. PEK-PI films, which were fabricated by casting from the CHCl3 solutions, are flexible and free-standing. Hybridization of PEK and PI will lead to the creation of organosoluble (except one PEK-PI), colorless transparent, and thermally stable materials. [ABSTRACT FROM AUTHOR]

A series of charge transfer cocrystals with fluorescence properties involving 1,2,4,5-tetracyanobenzene (TCNB, C10H2N4) as acceptor, fluorene (FR, C13H10) and its bromide 2-bromofluorene (2-BrFR, C13H9Br), carbazole (CZ, C12H9N) and its bromide 2-bromocarbazole (2-BrCZ, C12H8BrN) as donor were synthesized via cocrystal design strategies. The formation mechanism of the crystal structure was explored by density functional theory at the molecular level. The stacking structure of the cocrystal was formed by the combination of charge transfer interactions, π–π interactions and hydrogen bonding. The N atom of donors in TCNB–CZ and TCNB–2-BrCZ could enhance the charge transfer, appearing as a red shift of the fluorescence emission wavelength. Conversely, the Br atom in TCNB–2-BrFR and TCNB–2-BrCZ weakens the charge transfer, giving a blue shift in the fluorescence emission spectrum. The four new cocrystals exhibit tunable luminescence from green (529 nm) to yellow (552 nm) and to red (604 nm and 614 nm). It was found that the introduction of N and Br atoms in the assembly units can not only regulate the luminescence range of the cocrystals, but also adjust the luminescence efficiency, which provides a strategy for the development of promising organic luminescent materials. [ABSTRACT FROM AUTHOR]

Indenyl-(Ind) and fluorenyl-(Fl) substituted NHC-stabilized alanes and gallanes (NHC)·EH2R 1–12 (NHC = IiPrMe, IiPr, IMeMe; E = Al, Ga; R = Ind, Fl) were prepared via reaction of the corresponding NHC-iodoalanes and -gallanes with LiInd and LiFl, respectively. Analogously, the alane adducts with two Ind/Fl substituents (NHC)·AlHR213–18 (NHC = IiPrMe, IiPr, IMeMe; R = Ind, Fl) were obtained by using two equivalents of LiInd/LiFl. Elimination of indene and fluorene was induced thermally affording unusual dimeric and trimeric NHC-alane adducts {(NHC)·AlH2}2-μ-Fl 19–20 and {(NHC)·AlH-μ-R}n21–23 (R = Ind, Fl; n = 2, 3) with bridging indenyl and fluorenyl ligands. [ABSTRACT FROM AUTHOR]

In this study, the melt polycondensation reaction of 9,9'- bis(4-hydroxyphenyl)fluoride (BHPF) and diphenyl carbonate (DPC) was catalyzed using three ionic liquids (ILs) and a conventional alkali metal as catalysts. The optimal IL catalysts were determined to be [BMmim][BF4] ionic liquid catalysts, and the catalytic mechanism was investigated. Furthermore, the optimum process conditions were identified: the optimal amount of [BMmim][BF4] was 0.05 mol% based on DPC, the polycondensation temperature was set at 200°C for a duration of 3 h, followed by polymerization at 280°C for another 3 h. As a result, the Mn value of poly(9,9-bis(4-hydroxyphenyl) carbonate) (PFC) reached up to 41387 g/mol with a glass transition temperature band of approximately 254°C and Td-5% value of around 436°C. [ABSTRACT FROM AUTHOR]

In this work, we prepared a series of electron donor‐acceptor systems based on spiro[fluorene‐9,7'‐dibenzo[c,h]acridine]‐5'‐one (SFDBAO). Our SFDBAOs consist of orthogonally positioned fluorenes and aromatic ketones. By fine‐tuning the substitution of electron‐donating pyrenes, the complex interplay among different excited‐state decay channels and the overall impact of solvents on these decay channels were uncovered. Placing pyrene, for example, at the aromatic ketones resulted in a profound solvatochromism in the form of a bright charge‐transfer (CT) emission spanning from yellow to red‐NIR. In contrast, a dark non‐emissive CT was noted upon pyrene substitution at the fluorenes. In apolar solvents, efficient triplet‐excited state generation was observed for all SFDBAOs. Either charge transfer was concluded to mediate the intersystem crossing (ISC) in the case of pyrene substitution or the El‐Sayed rule was applicable when lacking pyrene substitution as in the case of SFABAO. In polar solvents, charge separation is the sole decay upon pyrene substitution. Moreover, competition between ISC and CT lowered the triplet‐excited state generation in SFDBAO. [ABSTRACT FROM AUTHOR]

A group of functionalized fluorene derivatives that are structurally similar to the cellular prion protein ligand N,N′-(methylenedi-4,1-phenylene)bis [2-(1-pyrrolidinyl)acetamide] (GN8) have been synthesized. These compounds show remarkable native fluorescence due to the fluorene ring. The substituents introduced at positions 2 and 7 of the fluorene moiety are sufficiently flexible to accommodate the beta-conformational folding that develops in amyloidogenic proteins. Changes in the native fluorescence of these fluorene derivatives provide evidence of transformations in the amyloidogenic aggregation processes of insulin. The increase observed in the fluorescence intensity of the sensors in the presence of native insulin or amyloid aggregates suggest their potential use as fluorescence probes for detecting abnormal conformations; therefore, the compounds can be proposed for use as "turn-on" fluorescence sensors. Protein–sensor dissociation constants are in the 5–10 μM range and an intermolecular charge transfer process between the protein and the sensors can be successfully exploited for the sensitive detection of abnormal insulin conformations. The values obtained for the Stern–Volmer quenching constant for compound 4 as a consequence of the sensor–protein interaction are comparable to those obtained for the reference compound GN8. Fluorene derivatives showed good performance in scavenging reactive oxygen species (ROS), and they show antioxidant capacity according to the FRAP and DPPH assays. [ABSTRACT FROM AUTHOR]

With the policy tilt and increased investment in research and development in the world, new energy vehicle technology continues to progress and the drive motor power density continues to improve, which puts forward higher requirements for the comprehensive performance of the core insulating material enameled wire enamel for drive motors. Polyimide (PI) has excellent electrical insulation properties, and heat resistance is often used to drive the motor winding insulation. To further improve the corona resistance and insulating properties of PI wire enamel varnish, in this paper, firstly, fluorene groups with a rigid conjugated structure were introduced into the molecular chain of the PI film by molecular structure modulation, and then uniformly dispersed alumina nanoclusters (AOCs) were introduced into the PI matrix by using an in situ growth process to inhibit the migration of high-energy electrons. The quantum size effect of the alumina nanoclusters was exploited to synergistically enhance the suppression and scattering of energetic moving electrons by PI-based composite films. The results show that the breakdown field strength of the PI-based composite film (MPI/1.0 vol% AOC) reaches 672.2 kV/mm, and the corona resistance life reaches 7.9 min, which are, respectively, 1.55 and 2.19 times higher than those of the initial PI film. A PI-based composite film with excellent insulating and corona resistance properties was obtained. [ABSTRACT FROM AUTHOR]

To obtain novel boron liquid crystals, we successfully combined MIDA boronates with chromophoric fluorene and fluorenone mesogenic units and studied the influence of alkoxy versus alkyl side chains by differential scanning calorimetry (DSC), polarising optical microscopy (POM) and X-ray diffraction (XRD). The fluorenes showed broader temperature ranges of the SmA phase compared to their fluorenone counterparts. By replacing the alkoxy side chains with alkyl side chains, the mesophase ranges could be significantly enlarged and the thermal stability increased. [ABSTRACT FROM AUTHOR]

In the continuation of previous studies on carbon‐rich meso‐tetraarylporphyrins featuring 2,7‐fluorene units at their periphery, the effect of changing the peripheral dendritic arms for linear arms on their oxygen‐photosensitizing ability, their fluorescence and their two‐photon absorption (2PA) properties is now analyzed. Thus, starburst porphyrins possessing up to twenty conjugated fluorenyl units were isolated and studied. More precisely, a series of five new free‐base porphyrins featuring fully conjugated arms incorporating an increasing number of fluorenyl groups connected via 1,2‐alkenyl spacers were synthesized, along with their Zn(II) complexes. Upon excitation in the arm‐centred π‐π* absorption band, an efficient energy transfer takes place from the peripheral fluorenyl units to the central porphyrin core, leading to intense red‐light emission and oxygen photosensitization by the latter. More interestingly, while the linear optical properties of these porphyrins were only slightly improved compared to those of their dendrimer analogues for photodynamic therapy (PDT) or fluorescence imaging, their 2PA cross‐sections were much more significantly boosted, evidencing the key role played by different structures on nonlinear optical properties. Finally, by comparison with other porphyrin‐based two‐photon photosensitizers reported in the literature, we show that these new "semi‐disconnected" starburst systems exhibit a remarkable trade‐off between intrinsic 2PA, fluorescence and oxygen photosensitization. [ABSTRACT FROM AUTHOR]

Background: In experimental studies, several polycyclic aromatic hydrocarbons (PAHs) have shown endocrine disrupting properties, but very few epidemiological studies have examined their impact on pubertal development and results have been heterogenous. Objective: To explore if maternal PAH exposure during pregnancy was associated with the offspring’s timing of pubertal onset. Methods: We studied 582 mother-daughter dyads originating from a population-based cohort in a rural setting in Bangladesh. Maternal urinary samples, collected in early pregnancy (on average, gestational week 8), were analyzed for monohydroxylated metabolites of phenanthrene (1-OH-Phe, Σ2-,3-OH-Phe, and 4-OH-Phe), fluorene (Σ2-,3-OH-Flu), and pyrene (1-OH-Pyr) using liquid chromatography with tandem mass spectrometry (LC-MS/MS). The girls were interviewed on two separate occasions concerning date of menarche, as well as breast and pubic hair development according to Tanner. Associations were assessed using Kaplan-Meier analysis and multivariable-adjusted Cox proportional hazards regression or ordered logistic regression. Results: In early pregnancy, the mothers’ median urinary concentrations of Σ1-,2-,3-,4-OH-Phe, Σ2-,3-OH-Flu, and 1-OH-Pyr were 3.25 ng/mL, 2.0 ng/mL, and 2.3 ng/mL respectively. At the second follow-up, 78 % of the girls had reached menarche, and the median age of menarche was 12.7 ± 0.81 years. Girls whose mothers belonged to the second and third quintiles of ΣOH-Phe metabolites had a higher rate of menarche, indicating a younger menarcheal age (HR 1.39; 95 % CI 1.04, 1.86, and HR 1.41; 95 % CI 1.05, 1.88, respectively), than girls of mothers in the lowest quintile. This trend was not observed in relation to either breast or pubic hair development. None of the other maternal urinary PAH metabolites or the sum of all thereof in early pregnancy were associated with age at menarche or pubertal stage. Conclusions: Indications of non-monotonic associations of prenatal phenanthrene exposure with the daughters’ age of menarche were found, warranting further investigation.

The title compound was synthesized from perfluoro-1-ethyltetralin and 1,2,3,4-tetrafluorobenzene under the action of antimony pentafluoride as a mixture of cis- and trans-isomers in a 71% isolated yield. The structure and cis-/trans-configuration of the isomers were determined by NMR (19F, 13C), 19F–19F COSY, and 19F–19F NOESY 2D NMR spectroscopy.

Synthesis of benzo[a]fluorene, benzo[c]fluorene, and benzo[j]fluoranthene have been accomplished from readily accessible enol ether precursors via a Lewis acid‐catalyzed Prins‐type cycloaromatization. Mechanistically, it was proposed that Lewis acids catalyze the generation of oxonium species, which accelerate subsequent annulation and aromatization. This protocol offers the benefit of an operationally simple, transition‐metal‐free, and air‐tolerant reaction condition, enabling gram‐scale syntheses of the desired products. The total synthesis of viridistratin A further supported this synthetic strategy for establishing polycyclic aromatic hydrocarbon architectures. [ABSTRACT FROM AUTHOR]

Environmental compartments polluted with animal charcoal from the skin and hide cottage industries are rich in toxic heavy metals and diverse hydrocarbon classes, some of which are carcinogenic, mutagenic, and genotoxic, and thus require a bio-based eco-benign decommission strategies. A shotgun metagenomic approach was used to decipher the microbiome, hydrocarbon degradation genes, and heavy metal resistome of a microbial consortium (FN8) from an animal-charcoal polluted site enriched with fluorene. Structurally, the FN8 microbial consortium consists of 26 phyla, 53 classes, 119 orders, 245 families, 620 genera, and 1021 species. The dominant phylum, class, order, family, genus, and species in the consortium are Proteobacteria (51.37%), Gammaproteobacteria (39.01%), Bacillales (18.09%), Microbulbiferaceae (11.65%), Microbulbifer (12.21%), and Microbulbifer sp. A4B17 (19.65%), respectively. The microbial consortium degraded 57.56% (28.78 mg/L) and 87.14% (43.57 mg/L) of the initial fluorene concentration in 14 and 21 days. Functional annotation of the protein sequences (ORFs) of the FN8 metagenome using the KEGG GhostKOALA, KofamKOALA, NCBI's conserved domain database, and BacMet revealed the detection of hydrocarbon degradation genes for benzoate, aminobenzoate, polycyclic aromatic hydrocarbons (PAHs), chlorocyclohexane/chlorobenzene, chloroalkane/chloroalkene, toluene, xylene, styrene, naphthalene, nitrotoluene, and several others. The annotation also revealed putative genes for the transport, uptake, efflux, and regulation of heavy metals such as arsenic, cadmium, chromium, mercury, nickel, copper, zinc, and several others. Findings from this study have established that members of the FN8 consortium are well-adapted and imbued with requisite gene sets and could be a potential bioresource for on-site depuration of animal charcoal polluted sites. [ABSTRACT FROM AUTHOR]

In one‐dimensional polycyclic aromatic hydrocarbons (PAHs) containing five‐ and six‐membered rings fused together, one key question is whether the structures possess a quinoidal or aromatic diradical character. Here, we generate such PAHs by reversible oxidation of PAH‐extended tetrathiafulvalenes (TTFs). Extended TTFs were thus prepared and studied for their geometrical properties (crystallography), redox properties, and UV/Vis/NIR/EPR characteristics as a function of charge state. The EPR measurements of radical cations showed unique features for each PAH‐TTF. The dications, formally composed of fluoreno[3,2‐b]fluorene and diindeno[1,2‐b:1′,2′‐i]anthracene cores, were experimentally found to exhibit singlet ground states. For the latter, calculations reveal the closed shell, quinoid singlet state to be isoenergetic with the open shell singlet diradical. Each charge state exhibited unique optical properties with radical cations absorbing strongly in the NIR region with signatures from π‐dimers for the large core. The experimental results were paralleled and supported by detailed computations, including spin density distribution calculations, EPR simulations, and nucleus independent chemical shift (NICS) xy scans. [ABSTRACT FROM AUTHOR]

Fluorene, as one of the important organic compounds widely used in the field of medicine and photoelectric materials, could damage human health even if it is extremely low in the environment. The development of ultrasensitive and easy-recyclable surface-enhanced Raman scattering (SERS) detection of trace fluorene is highly desired. In this work, a nanocomposite of Ag nanoparticles (Ag NPs) and porous g-C3N4 is synthesized by a facile method. The advantageous features of the as-prepared nanocomposite include a high SERS sensitivity due to the plasmonic effect of the Ag NPs, excellent recyclability due to the self-cleaning ability originating from the photocatalytic degradation of porous g-C3N4 under visible light irradiation, and good adsorption due to the large specific surface area of porous g-C3N4. The experimental results show that an ultralow detection limit of 1.35 × 10–13 M for R6G can be achieved. Especially, the nanocomposite exhibits excellent performance for the detection of fluorene with the detection limit of 3.11 × 10–11 M and multidetection of at least 13 cycles. The present research provides a nanocomposite with excellent synergistic activity of plasmonic enhancement and photocatalytic degradation for the recyclable SERS detection of trace fluorene. [ABSTRACT FROM AUTHOR]

The reaction of butyryl chloride with ethynylbenzene in the presence of AlCl3 afforded a mixture of the Z/E‐isomers of 1‐chloro‐2‐phenylhex‐1‐en‐3‐one. 1,2‐Diphenylethyne under these conditions gave a novel polycarbocycle core, 6aH‐benzo[a]fluorene. The chemical structure of 11‐chloro‐5,6‐diphenyl‐6a‐propyl‐6aH‐benzo[a]fluorene was established by means of IE‐MS, 1H, 13C NMR, COSY, HSQC, HMBC, and 2D INADEQUATE technique. [ABSTRACT FROM AUTHOR]

Organic and biological molecules with relatively weak C–H bonds can react with O2 via a free-radical reaction called autoxidation. The primary products of these peroxyl-radical-driven reactions are hydroperoxides, R2CHOOH. If autoxidation continues, the secondary oxidation of hydroperoxides is known to form ketones, R2C═O, but this mechanism is not well characterized. Importantly, we find that ketone formation produces a highly reactive hydroxyl radical, HO•. We can trap HO• using benzene as a solvent to form quantifiable amounts of phenol. Fluorene was chosen as a model system to study this secondary oxidation in great detail. Kinetic modeling allowed the measurement of rate constants for the primary and secondary autoxidation reactions as 11.3 and 25 mol L−1s−1, respectively. Density functional theory modeling likewise predicts a faster oxidation for the secondary autoxidation. This type of kinetic measurement and modeling approach could be useful to study the autoxidation of plastics, petrochemicals, and lipids. [ABSTRACT FROM AUTHOR]

Polycyclic aromatic hydrocarbons (PAHs) are hazardous organic micropollutants that are ubiquitous as well as recalcitrant to degradation. They are generally found in wastewater bodies with proximity to gas production, oil exploration, and other processing industries. Therefore, their clean-up and removal techniques are of high importance. In this work, a novel adsorbent was developed by modification of palm date seed-derived activated carbon (AC) with acrylic acid-co-crotonic acid polymer. The effectiveness of the produced polymer-modified AC (PM-AC) in the simultaneous aquatic removal of naphthalene and fluorene was studied systematically. The physicochemical characteristics of the developed PM-AC adsorbent were assessed by FTIR, SEM, and EDX. The equilibrium data are well in agreement with the Langmuir isotherm model and the adsorption capacity of the PM-AC was determined as 2.76 mg g−1 by considering this model. The adsorption mechanism of both PAHs onto the PM-AC adsorbent was well described by the pseudo-second-order kinetic model. The thermodynamic ΔG parameter showed the increased spontaneity of the PAHs adsorption with raising the temperature as the ΔH value confirmed the endothermic nature of the adsorption process. The π–π interactions were the key mechanisms of PAHs adsorption onto the prepared adsorbent. The PM-AC also demonstrated good adsorption performance in the case of a model wastewater sample containing some toxic heavy metals. The obtained findings revealed that the prepared PM-AC composite could be a promising adsorbent for developing cost-effective filters for the removal of PAHs from urban wastewaters. The PAHs levels were determined by using gas chromatography tandem mass spectrometry (GC–MS/MS). Recovery values were found nearly quantitative (≥ 95%). [ABSTRACT FROM AUTHOR]

Two solution‐processable semi‐alicyclic transparent polyimide (PI) films with improved high‐temperature dimensional stability and low‐optical retardations were prepared from the stereo‐isomeric alicyclic dianhydrides, 1S,2R,4S,5R‐hydrogenated pyromellitic dianhydride (ccHPMDA) and 1R,2S,4S,5R‐hydrogenated pyromellitic dianhydride (ctHPMDA) and an aromatic diamine, 9,9‐bis[4‐(4‐aminobenzamide)phenyl]fluorene (FDAADA), respectively. The alicyclic cyclohexane units in the dianhydride moiety endowed the derived PI‐1 (ccHPMDA‐FDAADA) and PI‐2 (ctHPMDA‐FDAADA) films good optical transparency, the rigid‐rod benzanilide units provided the PI films low coefficients of thermal expansion (CTE), and the fluorene units resulted in good solution processability and low‐optical retardations (Rth) for the PI films. The PI films exhibited the glass transition temperatures over 400°C and the CTE value of 33.2 × 10−6/K for PI‐1 and 29.0 × 10−6/K for PI‐2 in the temperature range of 50 ~ 250°C, respectively. In addition, the PI films showed good optical transparency in the ultraviolet–visible light region with the optical transmittances higher than 80% for PI‐1 film at the wavelength of 500 nm. The PI films exhibited the average refractive indices of 1.6505 for PI‐1 and 1.6485 for PI‐2 film, respectively. The birefringence values of the PI films were all lower than 0.01, resulting in the low‐optical anisotropies with the optical retardation (Rth) of 77 nm for PI‐1 film and 84 nm for PI‐2 film. [ABSTRACT FROM AUTHOR]

The thermal reaction of the anthracene oil (AO) of coal tar with (1-methylethenyl)-benzene in the temperature range of 270–380 °C was studied. The reaction affords isopropylbenzene and ethylbenzene as products of hydrogen transfer from AO to (1-methylethenyl)-benzene, as well as condensation products of (1-methylethenyl)benzene with components of AO. Thermal reactions of (1-methylethenyl)benzene with fluorene and acenaphthene (both are components of AO) were studied. The reaction products were characterized by gas chromatography/mass spectrometry, 1H NMR spectroscopy, and thermogravimetric analysis. [ABSTRACT FROM AUTHOR]

A series of π-conjugated compounds ending with 9,9-diethyl-1-phenyl-1,9-dihydrofluoreno[2,3-d]imidazole were conveniently synthesized by condensation of the key intermediate 9,9-diethyl-N2-phenyl-9H-fluorene-2,3-diamine with the corresponding symmetric aryl phthalaldehydes under very mild conditions. The structures of these compounds were confirmed by 1H NMR, 13C NMR, and HRMS. Their UV-Vis spectroscopy data, fluorescent spectroscopy data, and further details of the electronic properties from cyclic voltammetry measurements and theoretical calculations were studied. Most compounds possess good fluorescence-emitting ability with quantum yield of fluorescence values in the region of 0.36–0.92 and display emission within 449–513 nm depending on the molecular nature. [ABSTRACT FROM AUTHOR]