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Modulating the Photocyclization Reactivity of Diarylethenes through Changes in the Excited-State Aromaticity of the π-Linker.

ABSTRACT: Quantum chemical calculations are performed to explore if the reactivity of diarylethene switches toward photocyclization can be controlled by the excited-state aromaticity of their bridging π-linker. Using an archetypal diarylethene with a non-aromatic π-linker as a reference, completely different outcomes are found when the π-linker is allowed to become either aromatic (no reaction) or antiaromatic (fast reaction) upon photoexcitation. The results demonstrate a possibility to use the excited-state aromaticity concept for actual modulation of photochemical reactivity.

SUBMITTER: Oruganti B

PROVIDER: S-EPMC9442643 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Modulating the Photocyclization Reactivity of Diarylethenes through Changes in the Excited-State Aromaticity of the π-Linker.

Oruganti Baswanth B Wang Jun J Durbeej Bo B

The Journal of organic chemistry 20220823 17

Quantum chemical calculations are performed to explore if the reactivity of diarylethene switches toward photocyclization can be controlled by the excited-state aromaticity of their bridging π-linker. Using an archetypal diarylethene with a non-aromatic π-linker as a reference, completely different outcomes are found when the π-linker is allowed to become either aromatic (no reaction) or antiaromatic (fast reaction) upon photoexcitation. The results demonstrate a possibility to use the excited-s ...[more]

PMID: 35997595

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