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Photophysical behaviour of BODIPY-phenylacetylene macrocyclic dyads for light-harvesting applications.

ABSTRACT: The synthesis and study of a family of BODIPY-phenylacetylene macrocycles where donor groups have been added to the macrocycle in order to tune the physicochemical properties and absorption profile is reported. Energy transfer is observed between this phenylacetylene antennae and BODIPY core and fluorescence emission from the BODIPY, at any excitation wavelength, is consistent with energy transfer from the macrocycle.

SUBMITTER: Yousaf M

PROVIDER: S-EPMC9083918 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Photophysical behaviour of BODIPY-phenylacetylene macrocyclic dyads for light-harvesting applications.

Yousaf Muhammad M Zarate Ximena X Schott Eduardo E Lough Alan J AJ Koivisto Bryan D BD

RSC advances 20180810 50

The synthesis and study of a family of BODIPY-phenylacetylene macrocycles where donor groups have been added to the macrocycle in order to tune the physicochemical properties and absorption profile is reported. Energy transfer is observed between this phenylacetylene antennae and BODIPY core and fluorescence emission from the BODIPY, at any excitation wavelength, is consistent with energy transfer from the macrocycle. ...[more]

PMID: 35542483

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Project description:The excited-state dynamics of perylene-based bichromophoric light harvesting antenna systems has been tailored by systematic modification of the molecular structure and by using solvents of increasing polarity in the series toluene, chloroform, and benzonitrile. The antenna systems consist of blue light absorbing naphthalene monoimide (NMI) energy donors (D1, D2, and D3) and the perylene derived green light absorbing energy acceptor moieties, 1,7-perylene-3,4,9,10-tetracarboxylic tetrabutylester (A1), 1,7-perylene-3,4,9,10-tetracarboxylic monoimide dibutylester (A2), and 1,7-perylene-3,4,9,10-tetracarboxylic bisimide (A3). The design of these antenna systems is such that all exhibit ultrafast excitation energy transfer (EET) from the excited donor to the acceptor, due to the effective matching of optical properties of the constituent chromophores. At the same time, electron transfer from the donor to the excited acceptor unit has been limited by the use of a rigid and nonconjugated phenoxy bridge to link the donor and acceptor components. The antenna molecules D1A1, D1A2, and D1A3, which bear the least electron-rich energy donor, isopentylthio-substituted NMI D1, exhibited ultrafast EET (τEET ∼ 1 ps) but no charge transfer and, resultantly, emitted a strong yellow-orange acceptor fluorescence upon excitation of the donor. The other antenna molecules D2A2, D2A3, and D3A3, which bear electron-rich energy donors, the amino-substituted NMIs D2 and D3, exhibited ultrafast energy transfer that was followed by a slower (ca. 20-2000 ps) electron transfer from the donor to the excited acceptor. This charge transfer quenched the acceptor fluorescence to an extent determined by molecular structure and solvent polarity. These antenna systems mimic the primary events occurring in the natural photosynthesis, i.e., energy capture, efficient energy funneling toward the central chromophore, and finally charge separation, and are suitable building blocks for achieving artificial photosynthesis, because of their robustness and favorable and tunable photophysical properties.

Dataset Information

Photophysical behaviour of BODIPY-phenylacetylene macrocyclic dyads for light-harvesting applications.

Publications

Photophysical behaviour of BODIPY-phenylacetylene macrocyclic dyads for light-harvesting applications.

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