Dataset Information

BODIPY-Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands.

ABSTRACT: A series of energy transfer arrays, comprising a near-IR absorbing and emitting bacteriochlorin, and BODIPY derivatives with different absorption bands in the visible region (503-668 nm) have been synthesized. Absorption band of BODIPY was tuned by installation of 0, 1, or 2 styryl substituents [2-(2,4,6-trimethoxyphenyl)ethenyl], which leads to derivatives with absorption maxima at 503, 587, and 668 nm, respectively. Efficient energy transfer (>0.90) is observed for each dyad, which is manifested by nearly exclusive emission from bacteriochlorin moiety upon BODIPY excitation. Fluorescence quantum yield of each dyad in nonpolar solvent (toluene) is comparable with that observed for corresponding bacteriochlorin monomer, and is significantly reduced in solvent of high dielectric constants (DMF), most likely by photoinduced electron transfer. Given the availability of diverse BODIPY derivatives, with absorption between 500-700 nm, BODIPY-bacteriochlorin arrays should allow for construction of near-IR emitting agents with multiple and broadly tunable absorption bands. Solvent-dielectric constant dependence of ?f in dyads gives an opportunity to construct environmentally sensitive fluorophores and probes.

SUBMITTER: Meares A

PROVIDER: S-EPMC5873296 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Publications

BODIPY-Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands.

Meares Adam A Satraitis Andrius A Ptaszek Marcin M

The Journal of organic chemistry 20171122 24

A series of energy transfer arrays, comprising a near-IR absorbing and emitting bacteriochlorin, and BODIPY derivatives with different absorption bands in the visible region (503-668 nm) have been synthesized. Absorption band of BODIPY was tuned by installation of 0, 1, or 2 styryl substituents [2-(2,4,6-trimethoxyphenyl)ethenyl], which leads to derivatives with absorption maxima at 503, 587, and 668 nm, respectively. Efficient energy transfer (>0.90) is observed for each dyad, which is manifest ...[more]

PMID: 29119786

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Project description:The study of small donor molecules as the active component of organic solar cells continues to attract considerable attention due to the range of advantages these molecules have over their polymeric counterparts. Here we report the synthesis and solar cell fabrication of three BODIPY small molecule donors. Two of the dyes feature triphenylamine and phenothiazine as donor units attached to the meso and α-positions of the BODIPY core (TPA-PTZ-DBP and PTZ-TPA-BDP). Additionally, we have synthesised a push-pull derivative featuring phenothiazine moieties in the α-positions and a nitrobenzene in the meso-position (N-TPA-BDP) in order to investigate what effect this type of functionalisation has on the photovoltaic properties compared to the other dyes. The optoelectronic properties were investigated and the dyes showed broad absorption in the near-infrared with high extinction coefficients. Electrochemical measurements indicated good reversibility for the dyes redox processes. In contrast with the all-donor functionalised systems, N-TPA-BDP demonstrated extensive HOMO-LUMO overlap by DFT. The dyes were investigated as donor molecules in bulk heterojunction solar cells along with PC71BM, and under optimal donor to acceptor ratio PTZ-TPA-BDP showed the highest PCE of 1.62%. N-PTZ-BDP:PC71BM was the only blend to further improve upon thermal annealing reaching the highest conversion efficiency among the dyes of 1.71%. A morphology comprised of finely mixed donor and acceptor components is observed for BHJ blends of each of the three donors at their optimum fullerene content. Upon thermal annealing, these morphological features remain mostly the same for PTZ-TPA-BDP:PC71BM and TPA-PTZ-DBP:PC71BM blends whereas for N-PTZ-BDP:PC71BM the domains show a larger size. These dyes show that phenothiazine functionalisation of BODIPY is useful for solar cells because it gives strong and broad absorption extending to the near infra-red and materials with reversible redox properties - both of which are desirable for organic solar cells.

Dataset Information

BODIPY-Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands.

Publications

BODIPY-Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands.

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