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Macrocyclic Donor-Acceptor Dyads Composed of a Perylene Bisimide Dye Surrounded by Oligothiophene Bridges.

ABSTRACT: Two macrocyclic architectures comprising oligothiophene strands that connect the imide positions of a perylene bisimide (PBI) dye have been synthesized via a platinum-mediated cross-coupling strategy. The crystal structure of the double bridged PBI reveals all syn-arranged thiophene units that completely enclose the planar PBI chromophore via a 12-membered macrocycle. The target structures were characterized by steady-state UV/Vis absorption, fluorescence and transient absorption spectroscopy, as well as cyclic and differential pulse voltammetry. Both donor-acceptor dyads show ultrafast Förster Resonance Energy Transfer and photoinduced electron transfer, thereby leading to extremely low fluorescence quantum yields even in the lowest polarity cyclohexane solvent.

SUBMITTER: Bold K

PROVIDER: S-EPMC9299635 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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Macrocyclic Donor-Acceptor Dyads Composed of a Perylene Bisimide Dye Surrounded by Oligothiophene Bridges.

Bold Kevin K Stolte Matthias M Shoyama Kazutaka K Holzapfel Marco M Schmiedel Alexander A Lambert Christoph C Würthner Frank F

Angewandte Chemie (International ed. in English) 20211123 1

Two macrocyclic architectures comprising oligothiophene strands that connect the imide positions of a perylene bisimide (PBI) dye have been synthesized via a platinum-mediated cross-coupling strategy. The crystal structure of the double bridged PBI reveals all syn-arranged thiophene units that completely enclose the planar PBI chromophore via a 12-membered macrocycle. The target structures were characterized by steady-state UV/Vis absorption, fluorescence and transient absorption spectroscopy, a ...[more]

PMID: 34669254

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