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The investigation of molecular model systems is fundamental towards a deeper understanding of key photochemical steps in natural photosynthesis. Herein, we report an entirely non-covalent triad consisting of boron dipyrromethene (BDP), porphyrin (ZnP), and fullerene (C60). Non-covalent binding motifs such as an amidinium-carboxylate salt bridge as well as axial pyridyl-metal coordination offer substantial electronic coupling and establish efficient pathways for photoactivated energy and electron transfer processes along a well-tuned gradient. Experimental findings from steady-state and time-resolved spectroscopic assays, as well as (spectro-)electrochemical measurements corroborate the formation of BDP|ZnP|C60 in solution, on one hand, and significant communication in the excited states, on the other hand. BDP acts as an energy harvesting antenna towards ZnP, which eventually undergoes charge separation with C60 by electron transfer from ZnP to C60. Notably, full spectral deconvolution of the transient species was achieved, supporting the successful self-assembly as well as giving a clear view onto the occurring photophysical processes and their spectral footprints upon photoexcitation.

In this study, a series of diphenylalanine tetra-substituted porphyrin derivatives were synthesized and their self-assembly ability was extensively studied. Apart from investigating the impact of incorporating many peptide moieties onto a porphyrin molecule; another perspective was investigated as well, namely the connection of two different chromophore entities (porphyrin and BODIPY) onto the same diphenylalanine molecule. Interestingly, various supra-molecular nanostructures were observed depending on the solvent mixture as well as the protecting group of the peptides, namely spheres, plaques and fibrils. The obtained self-assemblies were studied via UV-vis absorption and emission spectroscopies. Mainly red shifting was observed, indicating the formation of [Formula: see text]-aggregates in the self-assembled state. However, in one case a blue shifted UV-vis spectrum was obtained suggesting the formation of [Formula: see text]-type aggregates. Concerning the porphyrin-diphenylalanine-BODIPY derivative, additional fluorescence studies were performed in order to examine a possible interaction between the two chromophores in the excited state. Indeed, the emission measurements indicated that upon photo-excitation of the BODIPY entity, a very efficient energy or electron transfer process takes place from the BODIPY molecule to the porphyrin macrocycle.

Free base 5,10,15,20 tetrakis 4 carboxylatophenyl porphyrin stands for the class of powerful porphyrin photosensitizers for singlet oxygen generation and light harvesting. The atomic level selectivity of dynamic UV pump N K edge probe X ray absorption spectroscopy in combination with time dependent density functional theory TD DFT gives direct access to the crucial excited molecular states within the unusual relaxation pathway. The efficient intersystem crossing, that is El Sayed forbidden and not facilitated by a heavy atom is confirmed to be the result of the long singlet excited state lifetime Qx 4.9 ns and thermal effects. Overall, the interplay of stabilization by conservation of angular momenta and vibronic relaxation drive the de excitation in these chromophores

The synthesis, characterization, and application in light‐emitting electrochemical cells (LECs) of two near‐infrared (NIR)‐emitting Pt‐porphyrins (Pt‐por) with none or 20 F atoms and their respective Pt‐por polyads containing from 1 to 4 BODIPY (BDP) units (PtBDP) connected via tetra‐fluorophenyl triazole spacer groups are reported. The functionalization of PtBDPs is tuned with respect to the number of BDP units and F atoms optimizing 1) the NIR emission through an efficient energy transfer from the BDP to the Pt‐por core, 2) the electronic structure to decouple charge transport via BDP and exciton formation at the Pt‐por, and 3) the ionic conductivity in thin films. A comprehensive rationale on how the molecular design rules the device performance is provided, achieving LECs with emission at 780 nm. This is realized using PtBDP‐2‐8, in which a host:guest strategy between BDP and Pt‐por in thin films is fully operative accompanied by an optimal ionic conductivity. This is supported by spectroelectrochemical findings and device analysis with both Pt‐por references and the PtBDP series. Overall, this work highlights that Pt‐porphyrins are efficient emitters in developing NIR LECs due to their rich functionalization, enabling to control charge transport, energy transfer, and ionic conductivities.

International audience; The utilization of solar energy via photoelectrochemical cells (PEC) towards hydrogen (H2) production is a promising approach in the field of artificial photosynthesis. In this work, the synthesis and complete characterization of the first covalently linked porphyrin‐cobalt diimine‐dioxime dyad (ZnP‐Co) is reported. The synthetic procedure that was followed is based on simple and high yielding reactions, without using any noble metal. Photophysical investigation of the dyad revealed sufficient electronic communication between the sensitizer and the catalyst in the excited state. Finally, NiO films were sensitized with ZnP‐Co and the H2‐evolving photoelectrochemical activity of the resulting photocathode was assessed. The modest performances could be rationalized thanks to photolysis and post‐operando characterizations of the system, thus providing some guidelines toward the design of more efficient porphyrin‐based assemblies.

Heavy-atom-free sensitizers forming long-living triplet excited states via the spin-orbit charge transfer intersystem crossing (SOCT-ISC) process have recently attracted attention due to their potential to replace costly transition metal complexes in photonic applications. The efficiency of SOCT-ISC in BODIPY donor-acceptor dyads, so far the most thoroughly investigated class of such sensitizers, can be finely tuned by structural modification. However, predicting the triplet state yields and reactive oxygen species (ROS) generation quantum yields for such compounds in a particular solvent is still very challenging due to a lack of established quantitative structure-property relationship (QSPR) models. Herein, we analyzed the available data on singlet oxygen generation quantum yields (F?) for a dataset containing > 70 heavy-atom-free BODIPY in three different solvents (toluene, acetonitrile, and tetrahydrofuran). In order to build reliable QSPR model, we synthesized a series of new BODIPYs containing different electron donating aryl groups in the meso position, studied their optical and structural properties along with the solvent dependence of singlet oxygen generation, which confirmed the formation of triplet states via the SOCT-ISC mechanism. For the combined dataset of BODIPY structures, a total of more than 5000 quantum-chemical descriptors was calculated including quantum-chemical descriptors using Density Functional Theory (DFT), namely M06-2X functional. QSPR models predicting F? values were developed using multiple linear regression (MLR), which perform significantly better than other machine learning methods and show sufficient statistical parameters (R = 0.88 ? 0.91 and q2 = 0.62 ? 0.69) for all three solvents. A small root mean squared error of 8.2% was obtained for F? values predicted using MLR model in toluene. As a result, we proved that QSPR and machine learning techniques can be useful for predicting F? values in different media and virtual screening of new heavy-atom-free BODIPYs with improved photosensitizing ability.

International audience; In the current work, we present the use of two free-base and two zinc-metallated porphyrin-ruthenium(II) polypyridine dyads, along with two reference porphyrin derivatives, as sensitizers in both n-and p-type DSSCs and DSPECs. Two of the dyads contain the well-known Ru(bpy)3 unit (HOOC-DMP-Ru(bpy)3 and HOOC-(Zn)DMP-Ru(bpy)3), while in the other two terpyridine-Ru(Cl)-bypiridine was used (HOOC-DMP-tpy-Ru and HOOC-(Zn)DMP-tpy-Ru). In all systems, the amide-bonding motif was utilized for the connection of the counterparts comprising each dyad. Photophysical investigation of the reported systems indicated sufficient electronic interactions for the dyads in their excited states (emission measurements). The photovoltaic measurements revealed that the presence of the ruthenium complex improves the overall performance of the dyads with the most efficient dyad being HOOC-(Zn)DMP-tpy-Ru in both n-and p-type DSSCs. Consequently, HOOC-(Zn)DMP-tpy-Ru was used to fabricate n-and p-DSPECs towards the oxidation of methoxy-benzyl alcohol and the reduction of CO2, respectively.

In this work a peptide nucleic acid (PNA) was covalently connected with two different chromophores, namely porphyrin and boron-dipyrromethene. To the best of our knowledge, this is the first example in the literature where a PNA unit is covalently linked to such chromophores. The self-assembly properties of the hybrids were examined through electron microscopy experiments by adopting the "good-bad" solvent self-assembly protocol. For both hybrids (PNA-TPP and PNA-BDP) we were able to observe distinctive supramolecular architectures. During these studies we investigated the influence of the solvent system, the concentration and the deposition method on the morphology of the formed nanostructures. In the case of PNA-TPP under all examined conditions well-formed nanospheres were obtained. Interestingly, in the PNA-BDP hybrid by simply altering the solvent mixture, self-assemblies of two different morphologies were formed (spherical and flake shaped). Absorption and emission studies suggested the formation of J-aggregates in all the obtained nanostructures. The nano-architectures assembled by PNA conjugates are capable of light-harvesting and producing hydrogen using Pt nanoparticles as a photocatalyst.

In this study, we report the preparation of two novel zinc-porphyrin derivatives (ZnP-3DoH-click-CNCOOH and ZnP-3DoH-click-COOH) and two reference compounds (ZnP-3DoH-CNCOOH and ZnP-3DoH-COOH) as sensitizers in dye-sensitized solar cells (DSCs). The photo-physical and electrochemical measurements along with the computational studies suggest that the four synthesized porphyrin derivatives exhibit appropriate light absorption characteristics as well as suitable molecular orbital levels for their use as sensitizers in DSCs. All the modified zinc-porphyrin complexes bear hexyloxy chains at the ortho-positions of their three phenyl rings and contain either a carboxylic or a cyanoacrylic acid as anchoring group. In the zinc-porphyrin derivatives ZnP-3DoH-click-CNCOOH and ZnP-3DoH-click-COOH, a spacer with an electron withdrawing unit was incorporated between the porphyrin ring and each anchoring group. More specifically, the triazole ring was used as a spacer since it is considered to be a highly efficient electron transfer bridge. In addition, the pentafluoro-phenyl ring was selected due to its strong electron withdrawing ability in both final derivatives (ZnP-3DoH-click-CNCOOH and ZnP-3DoH-click-COOH). Following this strategy, fourfold and eightfold increase of the device performance was observed regarding ZnP-3DoH-click-CNCOOH and ZnP-3DoH-click-COOH, respectively, when compared to the efficiencies achieved with the reference compounds (ZnP-3DoH-COOH and ZnP-3DoH-CNCOOH). A more detailed interpretation of the charge dynamics in these devices was carried out using charge extraction (CE) and open-circuit voltage decay (OCVD) measurements.

Herein, we report on the study of supramolecular assemblies based on polyoxometalates (POMs) upon their modification with amino acids. Two POM-amino acid hybrids were synthesized by coupling a functionalized Keggin type polyoxoanion [PW11O39{Sn(C6H4)C[triple bond, length as m-dash]C(C6H4)COOH}]4- with carboxyl-protected (methyl-ester) phenylalanine or diphenylalanine peptides. Surprisingly, all compounds, including the initial POM, formed supramolecular nanospheres in different solvent mixtures, which were examined by scanning electron microscopy (SEM). Molecular dynamics (MD) simulations for the POM-amino acid species revealed that the hydrophobic forces are mainly responsible for the initial aggregation into incipient micelle type structures, in which the organic arms are buried inside the aggregate while POM polar heads are more exposed to the solvent with tetrabutyl-ammonium counter cations acting as linkers.

Herein, we present the synthesis of a series of boron-dipyrromethane (BDP) derivatives bearing diphenylalanine (FF) at their meso position via amide bond coupling. The BDP-FF bioconjugates are able to form self-assembled materials with different morphologies. By altering various parameters such as the protecting group of the FF peptide or the solvent system of the self-assembly process, we were able to obtain either fibrillar or spherical nanostructures. Furthermore, we confirmed that both the formation as well as the dissociation of the self-assemblies is a reversible procedure that can be achieved by simply altering the solvent mixture. Electronic circular dichroism (ECD) studies demonstrated a characteristic mirror image relationship regarding the FLFL and FDFD enantiomers, revealing the chiral nature of the obtained materials. Interestingly, an intense excitonic bisignate signal was observed in the ECD spectrum of the fibrillar structures, whereas the spherical assemblies remained ECD silent. What is more, the electronic circular dichroism studies were supported by quantum chemical calculations.

This study reports the synthesis of two novel zinc porphyrin families bearing four or eight alkoxy chains at their peripheral phenyl rings, with the length of the alkoxy chains ranging from 2, to 6, and to 12 carbon atoms. All zinc porphyrin derivatives were fully characterized with respect to their photophysical and electrochemical features. The zinc porphyrins could be processed into thin films which, depending on the length of the alkoxy chains on the aryl substituents, were found to be either of an ordered or a disordered nature, as it is revealed by spectroscopic and microscopic techniques. The films containing ordered self-assemblies displayed significantly enhanced electrical conductivity compared to the disordered films. This led to remarkable differences regarding their electroluminescence response that occurs at lower bias. Furthermore, their luminous efficiency was of almost one order of magnitude higher than that of disordered films.

In this review, we report the synthesis and photophysical studies of porphyrin–4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) compounds linked either with different covalent bonds or with axial coordination to metalloporphyrin. BODIPY moiety significantly increases the light absorption capability of porphyrins by efficient BODIPY to porphyrin excitation energy transfer. The type of linkage between the two chromophores significantly affects the energy transfer efficiency. The most efficient energy transfer was proved for compounds linked via a cyanuric chloride bridge (∼99% quenching). Therefore, this type of bond seems to be more appropriate choice in constructing porphyrin–BODIPY assemblies for light harvesting applications. Moreover, the functionalization of the conjugates with fullerenes appears to be interesting electron transfer dynamics in the excited state.

In this study, a new modified C60 derivative with an oPE/oPPV conjugated bridge bearing two pyridyl groups has been used in combination with a flexible porphyrin dimer (ZnP2) to construct an electron donor/acceptor hybrid (C60-dipyr·ZnP2). This hybrid is based on metal to ligand coordination between the zinc centers of the porphyrin dimer and the two pyridyl groups that oPE/oPPV linker bears. In order to investigate the interactions between the electron donor and acceptor entities, both in the ground state and in the excited states, comprehensive photophysical assays have been carried out. In particular, both absorption and fluorescence titrations provided evidence for strong interactions between the electron donor and the electron acceptor within the hybrid. A binding constant (Kass) in the order of 5.0 × 105 M–1 has been derived. Furthermore, transient absorption measurements revealed intramolecular electron-transfer from the photoexcited porphyrin dimer (ZnP2) to the fullerene derivative (C60-dipyr), l...

Light activation of dyads containing porphyrins and a catalytic ruthenium complex having a high oxidation potential (~1 V vs SCE) is investigated by time-resolved spectroscopy. It is shown that activation of the ruthenium complex occurs through oxidative quenching of the chromophore in the presence of a reversible electron acceptor. Despite the lack of driving force for intramolecular electron transfer, an efficient intramolecular oxidation of the catalyst is observed, suggesting that porphyrins are attractive chromophores to activate oxidation catalysts throughout the visible spectrum.

Natural photosynthesis inspired the scientific community to design and synthesize molecular assemblies that possess advanced light-harvesting and electron-transfer features. In this review, we present the preparation and the photophysical investigation of novel porphyrin−fullerene hybrids acting as artificial photosynthetic systems. Porphyrinoids stand as chlorophyll analogues and have emerged as suitable photosensitizers in supramolecular electron donor−acceptor hybrids. Fullerenes (C60) are versatile electron acceptors with small reorganization energy and low reduction potentials. The novel derivatives presented herein mimic the fundamental features of the photosynthetic reaction center, namely, light harvesting, charge separation, and charge transport. To this end, a comprehensive analysis on these key processes that occur in various porphyrin−fullerene entities is illustrated in this work.

Solar energy is undoubtedly one of the most exploitable energy sources providing a potential solution to address the environmental issues deriving from the excessive use of fossil fuels. Over the last few years p-type dye sensitized solar cells (p-DSCs) have attracted substantial attention, since their incorporation with n-type DSCs could potentially lead to more efficient tandem cell pn-DSCs. Moreover, new research has been devoted to dye-sensitized photoelectrochemical cells (DSPECs), in which solar energy is utilized to generate hydrogen via water splitting. This article provides a summary of recent sensitizers employed in dye-sensitized NiO photocathodes for DSC and DSPEC, discussing approaches to enhance their overall performance. In particular, we intend to provide new directions through molecular design of new dyes and stimulate additional research development in the fields of DSCs and DSPECs.

We report on the synthesis, characterization and photophysical properties of a donor-bridge-acceptor supramolecular hybrid system, consisting of a tetrapyridyl fullerene derivative (C60-tpyr) as electron acceptor, with the four pyridyl groups as part of oligophenyleneethynylene/phenylenevinylene bridges, and zinc porphyrin dimers (ZnP)2 as electron donor species. Based on the metal-to-ligand coordination between the zinc metal centers of (ZnP)2 and the four pyridyl entities of C60-tpyr, a strong binding constant (5 × 105 M-1) for the formation of C60-tpyr·[(ZnP)2]2 was evidenced. Insights into the electronic interactions between the photoactive (ZnP)2 units and C60-tpyr emanated from complementary physicochemical assays, which were further supported by theoretical calculations. Notably, the absorption and emission titration assays revealed strong interactions between the electron donor and acceptor species within C60-tpyr·[(ZnP)2]2, both in the ground and excited state. Moreover, femtosecond and nanosecond laser photolysis transient absorption measurements were performed and provided solid evidence for intramolecular electron transfer processes derived from the singlet excited state of (ZnP)2 to C60-tpyr. Comparison with systems in which either four monomeric zinc porphyrins (ZnP) were complexed with C60-tpyr or a (ZnP)2 was coordinated with a dipyridylfullerene revealed the beneficial role of C60-tpyr in increasing the lifetime of charge-separation.

Two novel zinc-metallated porphyrins (ZnP3C and ZnP6C), bearing three and six long alkoxy chains at the periphery of each porphyrin and a terminal carboxylic acid group, have been synthesized and fully characterized. Photophysical and electrochemical measurements demonstrated that the two sensitizers possess suitable frontier orbital energy levels for their use as sensitizers in DSSCs. The solar cells sensitized by ZnP3C and ZnP6C were fabricated resulting in power conversion efficiencies (PCEs) of 5.03 and 6.09%, respectively. As shown by photovoltaic measurements (J–V curves) and incident photon-to-current conversion efficiency (IPCE) spectra of the two solar cells, the higher PCE value of the latter is attributed to its enhanced photovoltaic parameters, and particularly its enhanced short circuit current (Jsc). This is related to the stronger absorption profile of the sensitizing dye ZnP6C and the higher dye loading of the corresponding solar cell. Furthermore, electrochemical impedance spectroscopy (EIS) showed that the DSSC based on ZnP6C exhibits a longer electron lifetime (τe) and more effective charge recombination resistance between the injected electrons and the electrolyte.

International audience; Two novel porphyrins, ZnP(SP)CNCOOH and ZnPCNCOOH, bearing cyanoacrylic acid as an anchoring group were synthesized. Porphyrin ZnP(SP)CNCOOH contains a π-conjugated spacer (SP) for improved electronic communication between the dye and the TiO2 electrode. The spacer bears polyethylene glycol chains to prevent dye aggregation and to enhance solubility of the dye. Electrochemical measurements and theoretical calculations suggest that both porphyrins are promising sensitizers for dye-sensitized solar cells (DSSCs), as their molecular orbital energy levels favor electron injection and dye regeneration. Solar cells sensitized by ZnP(SP)CNCOOH and ZnPCNCOOH show power conversion efficiencies of 7.61 and 5.02 %, respectively. Photovoltaic measurements (J–V curves and incident photon to current conversion efficiency spectra) show that higher short-circuit current (Jsc) and open-circuit voltage (Voc) values are reached for the solar cell based on ZnP(SP)CNCOOH. This can be mainly ascribed to suppressed charge recombination, as indicated by their electrochemical impedance spectra.

Herein, the synthesis of three covalently linked donor-acceptor zinc porphyrin-fullerene (ZnP-C-60) dyads (C(60)trZnPCOOH, C(60)trZnPtrCOOH and C60ZnPCOOH) is described, and their application as sensitizers in NiO-based dye-sensitized solar cells (DSCs) is discussed. To the best of our knowledge, this is the first example where covalently linked ZnP-C-60 dyads have been used as chromophores in NiO-based DSCs. In an effort to examine whether the distance of the chromophore from the electron acceptor entity and/or the NiO surface affects the performance of the cells, a triazole ring was introduced as a spacer between ZnP and the two peripheral units C-60 and -COOH. The triazole ring was inserted between ZnP and C-60 in dyad C(60)trZnPCOOH, whereas both the anchoring group and C-60 were connected to ZnP through triazole spacers in C(60)trZnPtrCOOH, and dyad C60ZnPCOOH did not contain any triazole linker. Photophysical investigation performed by ultrafast transient absorption spectroscopy in solution and on the NiO surface demonstrated that all the porphyrin-fullerene dyads exhibited long-lived charge-separated states due to electron shifts from the reduced porphyrin core to C-60. The transient experiments performed in solution showed that the presence of triazole ring influenced the photophysical properties of the dyads C(60)trZnPCOOH and C(60)trZnPtrCOOH and in particular, increased the lifetime of the charge-separated states compared to that of the C60ZnPCOOH dyad. On the other hand, the corresponding studies on the NiO surface proved that the triazole spacer has a rather moderate impact on the charge separation (NiO-ZnP center dot+-C-60(center dot-)) and charge recombination (NiO-(3)*ZnP-C-60) rate constants. All three dyads exhibited enhanced performance in terms of photovoltaic measurements with more than threefold increase compared to the reference compound PhtrZnPCOOH in which the C-60 acceptor is absent. Two different electrolytes were examined (I-3(-)/I- and Co-III/II) and in most cases, the presence of the triazole ring enhanced their photovoltaic performance. The best performing dyad in I-3(-)/I- was C(60)trZnPCOOH (PCE = 0.076%); in Co-III/II, the best performing dyad was C(60)trZnPtrCOOH (PCE = 0.074%).

A novel π-conjugated oligo(phenylenevinylene) (oPPV) (or LC) was prepared, as a new organic dye for dye-sensitized solar cells (DSSC), which contains a cyanoacrylic acid group on one end and a pyridyl group on the other. Solar cells sensitized by LC were fabricated, and were found to exhibit a power conversion efficiency (PCE) value of 2.45%. Furthermore, we describe the formation of a supramolecular dyad (ZnTPP–LC) via a metal–ligand bond between LC, since its pyridyl group allows it to interact with several metal centers, and zinc-tetraphenyl-porphyrin (ZnTPP) onto the photoelectrode's TiO2 surface of the solar cell. More specifically, LC was bound at first onto TiO2 with its cyanoacrylic acid anchoring group, and then a metal–ligand supramolecular bond was formed, with the addition of a porphyrinic solution, between the nitrogen atom of LC's pyridyl group and the zinc. ZnTPP–LC solar cell was then fabricated resulting in a record PCE value of 5.27% concerning the supramolecular DSSCs. As shown by photovoltaic measurements (J–V curves) and incident photon to current conversion efficiency (IPCE) spectra of the two solar cells, the higher PCE value of the supramolecular one can be attributed to its enhanced photovoltaic parameters, and particularly its enhanced short circuit current (Jsc). This Jsc improvement is due to ZnTPP–LC's higher light-harvesting efficiency and the larger electron injection of both ZnTPP and LC into TiO2's conduction band (CB) of the corresponding solar cell. These results are in accordance with electrochemical impedance spectra (EIS) of the DSSCs, which revealed longer electron lifetime, higher charge recombination resistance and shorter electron transport time for the solar cell based on ZnTPP–LC as compared to the one sensitized by LC.

Sequential photoinduced energy transfer followed by electron transfer leading to the formation of charge separated states in a newly assembled series of supramolecular triads comprised of boron dipyrromethenes (BODIPY or BDP), aluminum porphyrin (AlTPP) and C60 is demonstrated. In the present strategy, the energy donor (BDP) and electron acceptor (C60) were axially positioned to the plane of AlTPP via the central metal. The structural integrity of the newly synthesized compounds and self-assembled systems were fully established using spectral, electrochemical and computational methods. Thermodynamic feasibility of energy transfer from 1BDP* to AlTPP and subsequent electron transfer from 1AlTPP* to generate BDP-AlTPP•+-C60•– charge separated states was derived from free-energy calculations. Occurrence of ultrafast energy transfer from 1BDP* to AlTPP was established from studies involving steady-state and time-resolved emission, as well as femtosecond transient spectroscopic techniques. The BDP-AlTPP•+-C60•...

The syntheses, photophysical/electrochemical characterizations of different metallated porphyrins -i.e., Zn(2+), Pt(2+), Pd(2+), and Sn(4+) porphyrins - as well as their first application in light-emitting electrochemical cells are provided. A direct comparison demonstrates that depending on the metallation either efficient (Pt-por) or stable (Zn-por) devices are achieved, demonstrating that the choice of the metal core is a key aspect for future developments.

Heavy‐atom‐free sensitizers forming long‐living triplet excited states via the spin‐orbit charge transfer intersystem crossing (SOCT‐ISC) process have recently attracted attention due to their potential to replace costly transition metal complexes in photonic applications. The efficiency of SOCT‐ISC in BODIPY donor‐acceptor dyads, so far the most thoroughly investigated class of such sensitizers, can be finely tuned by structural modification. However, predicting the triplet state yields and reactive oxygen species (ROS) generation quantum yields for such compounds in a particular solvent is still very challenging due to a lack of established quantitative structure‐property relationship (QSPR) models. In this work, the available data on singlet oxygen generation quantum yields (ΦΔ) for a dataset containing >70 heavy‐atom‐free BODIPY in three different solvents (toluene, acetonitrile, and tetrahydrofuran) were analyzed. In order to build reliable QSPR model, a series of new BODIPYs were synthesized that bear different electron donating aryl groups in the meso position, their optical and structural properties were studied along with the solvent dependence of singlet oxygen generation, which confirmed the formation of triplet states via the SOCT‐ISC mechanism. For the combined dataset of BODIPY structures, a total of more than 5000 quantum‐chemical descriptors was calculated including quantum‐chemical descriptors using density functional theory (DFT), namely M06‐2X functional. QSPR models predicting ΦΔ values were developed using multiple linear regression (MLR), which perform significantly better than other machine learning methods and show sufficient statistical parameters (R=0.88–0.91 and q2=0.62–0.69) for all three solvents. A small root mean squared error of 8.2 % was obtained for ΦΔ values predicted using MLR model in toluene. As a result, we proved that QSPR and machine learning techniques can be useful for predicting ΦΔ values in different media and virtual screening of new heavy‐atom‐free BODIPYs with improved photosensitizing ability., Data on singlet oxygen generation for a library of heavy‐atom‐free BODIPYs undergoing spin‐orbit charge transfer intersystem crossing (SOCT‐ISC) were used to build quantitative structure‐property relationship (QSPR) predictive models. These models estimate quantum yields of singlet oxygen (1O2) generation for a given photosensitizer structure in nonpolar, moderately polar and highly polar solvent. This allows for virtual screening of environment‐activatable BODIPY photosensitizers and hence speeding up the development of new lead compounds for photomedicine.