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A series of iridium(III) triimine complexes incorporating 2,2':6',2″-terpyridine ( terpy ) and 2,6-bis(thiazol-2-yl)pyridine ( dtpy ) derivatives were successfully designed and synthesized to investigate the impact of the peripheral rings (pyridine, thiazole) and substituents (thiophene, bithiophene, EDOT) attached to the triimine skeleton on their photophysical properties. The Ir(III) complexes were fully characterized using IR, 1 H, elemental analysis and single crystal X-ray analysis. Their thermal properties were evaluated using TGA measurements. Photoluminescence spectra of [IrCl 3 L 1-6 ] were investigated in solution at 298 and 77 K. The experimental studies were accompanied by DFT/TDDFT calculations. The photophysical properties of the synthesized triimine ligands and Ir(III) complexes were studied in detail by electronic absorption and emission. In solution, they exhibited photoluminescence quantum yields ranging from 1.27% to 5.30% depending on the chemical structure. The experimental research included DFT/TDDFT calculations. The photophysical properties of the synthesized triimine ligands and Ir(III) complexes were conducted using electronic absorption and emission techniques. In solution, they displayed photoluminescence quantum yields ranging from 1.27% to 5.30% depending on the chemical structure.

Electrochromism of organic compounds is a well-known phenomenon; however, nowadays, most research is focused on anodic coloring materials. Development of efficient, cathodic electrochromic materials is challenging due to the worse stability of electron accepting materials compared with electron donating ones. Nevertheless, designing stable cathodic coloring organic materials is highly desired-among other reasons-to increase the coloration performance. Hence, four phthalimide derivatives named 1,5-PhDI, 1,4-PhDI, 2,6-PhDI and 3,3'-PhDI were synthesized and analyzed in depth. In all cases, two imide groups were connected via naphthalene (1,5-PhDI, 1,4-PhDI, 2,6-PhDI) or 3,3'-dimethylnaphtidin (3,3'-PhDI) bridge. To observe the effect of chemical structure on physicochemical properties, various positions of imide bond were considered, namely, 1,5- 1,4- and 2,6-. Additionally, a compound with the pyromellitic diimide unit capped with two 1-naphtalene substituents was obtained. All compounds were studied in terms of their thermal behavior, using differential calorimetry (DSC) and thermogravimetric analysis (TGA). Moreover, electrochemical (CV, DPV) and spectroelectrochemical (UV-Vis and EPR) analyses were performed to evaluate the obtained materials in terms of their application as cathodic electrochromic materials. All obtained materials undergo reversible electrochemical reduction which leads to changes in their optical properties. In the case of imide derivatives, absorption bands related to both reduced and neutral forms are located in the UV region. However, importantly, the introduction of the 3,3'-dimethylnaphtidine bridge leads to a noticeable bathochromic shift of the reduced form absorption band of 3,3'-PhDI. This indicates that optimization of the phthalimide structure allows us to obtain stable, cathodic electrochromic materials.

Three new azomethines based on triphenylamine with two or three substituents were obtained. Chemical structure and purity were confirmed by 1 H NMR, FTIR elemental analysis and mass spectroscopy. The investigations were focused on the relationship between chemical structure and properties important for optoelectronic materials. Thus, the studies of thermal, optical and electrochemical properties were carried out based on differential scanning calorimetry, thermogravimetric analysis, electronic absorption, photoluminescence and cyclic voltammetry measurements. The ongoing consideration of experimental results was complemented by theoretical calculations using the density functional theory method. The donor activity of obtained compounds was tested in bulk-heterojuntion photovoltaic cells with structure ITO/PEDOT:PSS/imine:PCBM/Al and ITO/PEDOT:PSS/imine:P3HT:PCBM/Al). The effect of the presence of the amino-thiophene-3,4-dicarboxylic acid diethyl ester groups and various number of hexyloxyphenyl units on imines properties was demonstrated.

In this research, six novel unsymmetrical imino-1,8-naphthalimides (AzNI) were synthesized. Comprehensive thermal (thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), optical (UV-Vis, photoluminescence), and electrochemical (CV, DPV) studies were carried out to characterize these new compounds. The molecules showed the onset of thermal decomposition in the temperature range 283-372 °C and molecular glass behavior. Imino-1,8-naphthalimides underwent reduction and oxidation processes with the electrochemical energy band gap (E g ) below 2.41 eV. The optical properties were evaluated in solvents with different polarities and in the solid-state as a thin films and binary blends with poly( N -vinylcarbazole): (2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole) (PVK:PBD). Presented compounds emitted blue light in the solutions and in the green or violet spectral range in the solid-state. Their ability to emit light under external voltage was examined. The devices with guest-host structure emitted light with the maximum located in the blue to red spectral range of the electroluminescence band (EL) depending on the content of the AzNI in the PVK:PBD matrix (guest-host structure).

The structure-property correlations and control of electronic excited states in transition metal complexes (TMCs) are of high significance for TMC-based functional material development. Within these studies, a series of Re(I) carbonyl complexes with aryl-substituted 2,6-di(thiazol-2-yl)pyridines (Ar n -dtpy) was synthesized, and their ground- and excited-state properties were investigated. A number of condensed aromatic rings, which function as the linking mode of the aryl substituent, play a fundamental role in controlling photophysics of the resulting [ReCl(CO) 3 (Ar n -dtpy-κ 2 N)]. Photoexcitation of [ReCl(CO) 3 (Ar n -dtpy-κ 2 N)] with 1-naphthyl-, 2-naphthyl-, 9-phenanthrenyl leads to the population of 3 MLCT. The lowest triplet state of Re(I) chromophores bearing 9-anthryl, 2-anthryl, 1-pyrenyl groups is ligand localized. The rhenium(I) complex with appended 1-pyrenyl group features long-lived room temperature emission attributed to the equilibrium between 3 MLCT and 3 IL/ 3 ILCT. The excited-state dynamics in complexes [ReCl(CO) 3 (9-anthryl-dtpy-κ 2 N)] and [ReCl(CO) 3 (2-anthryl-dtpy-κ 2 N)] is strongly dependent on the electronic coupling between anthracene and {ReCl(CO) 3 (dtpy-κ 2 N)}. Less steric hindrance between the chromophores in [ReCl(CO) 3 (2-anthryl-dtpy-κ 2 N)] is responsible for the faster formation of 3 IL/ 3 ILCT and larger contribution of 3 ILCT anthracene → dtpy in relation to the isomeric complex [ReCl(CO) 3 (9-anthryl-dtpy-κ 2 N)]. In agreement with stronger electronic communication between the aryl and Re(I) coordination centre, [ReCl(CO) 3 (2-anthryl-dtpy-κ 2 N)] displays room-temperature emission contributed to by 3 MLCT and 3 IL anthracene / 3 ILCT anthracene → dtpy phosphorescence. The latter presents rarely observed phenomena in luminescent metal complexes.

The paper presents synthesis and characterization of nine new thiazolyl-(phenyldiazenyl)-2 H -chromen-2-one dyes. The impact of substituent structure in thiazole ring in the synthesized azocoumarin derivatives on electrochemical properties, photoisomerization process and photovoltaic response was examined. The dyes were electrochemically active and undergo reduction and oxidation processes. They showed low electrochemically estimated energy band gap in the range of 1.71-2.13 eV. Photoisomerization process of the synthesized molecules was studied in various solvents such as ethanol, chloroform and N , N -dimethylformamide (DMF) upon the UV illumination. It was found that novel azodyes showed reversible trans - cis - trans isomerization and exhibited long thermal back to the trans form, that was even 7 days in DMF. Selected azocoumarin were molecularly dispersed in polystyrene for preparation of guest-host azopolymer systems to study the cis - trans thermal isomerization of obtained dyes in solid state. The photovoltaic activity of the azochromophores was tested in bulk-heterojunction solar cells. They acting as weak donors in device with structure ITO/PEDOT:PSS/dye:PC70BM/Al. No photovoltaic response of cells with azocoumarin derivatives bearing 4-fluorobenzene, 3,4-dichlorobenzene, or 4-(1-adamantyl) unit was found. Additionally, dye which showed the best activity was examined in three-component solar cells ITO/PEDOT:PSS/PTB7:PC70BM:dye/PFN/Al.

A new series of 1,8-naphtalimides containing an imine bond at the 3-position of the naphthalene ring was synthesized using 1 H, 13 C NMR, FTIR, and elementary analysis. The impact of the substituent in the imine linkage on the selected properties and bioimaging of the synthesized compounds was studied. They showed a melting temperature in the range of 120-164 °C and underwent thermal decomposition above 280 °C. Based on cyclic and differential pulse voltammetry, the electrochemical behavior of 1,8-naphtalimide derivatives was evaluated. The electrochemical reduction and oxidation processes were observed. The compounds were characterized by a low energy band gap (below 2.60 eV). Their photoluminescence activities were investigated in solution considering the solvent effect, in the aggregated and thin film, and a mixture of poly( N -vinylcarbazole) (PVK) and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (50:50 wt.%). They demonstrated low emissions due to photoinduced electron transport (PET) occurring in the solution and aggregation, which caused photoluminescence quenching. Some of them exhibited light emission as thin films. They emitted light in the range of 495 to 535 nm, with photoluminescence quantum yield at 4%. Despite the significant overlapping of its absorption range with emission of the PVK:PBD, incomplete Förster energy transfer from the matrix to the luminophore was found. Moreover, its luminescence ability induced by external voltage was tested in the diode with guest-host configuration. The possibility of compound hydrolysis due to the presence of the imine bond was also discussed, which could be of importance in biological studies that evaluate 3-imino-1,8-naphatalimides as imaging tools and fluorescent materials for diagnostic applications and molecular bioimaging.

In this paper, six novel symmetrical bis-(imino-1,8-naphthalimides) differing in core and N-substituent structure were synthesized, and their thermal (TGA, DSC), optical (UV-Vis, PL), electrochemical (DPV, CV) properties were evaluated. The compounds were stable to 280 °C and could be transferred into amorphous materials. Electrochemical investigations showed their ability to occur reductions and oxidations processes. They exhibited deep LUMO levels of about -3.22 eV and HOMO levels above -5.80 eV. The optical investigations were carried out in the solutions (polar and non-polar) and in films and blends with PVK:PBD. Bis-(imino-1,8-naphthalimides) absorbed electromagnetic radiation in the range of 243-415 nm and emitted light from blue to yellow. Their capacity for light emission under voltage was preliminarily tested in devices with an active layer consisting of a neat compound and a blend with PVK:PBD. The diodes emitted green or red light.