Effect of Twisting on the Capture and Release of Singlet Oxygen by Tethered Twisted Acenes

Anjan Bedi, Amit Manor Armon, Ori Gidron*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

The use of polyaromatic hydrocarbons to capture and release singlet oxygen is of considerable importance in materials chemistry, synthesis, and photodynamic therapy. Here we studied the ability of a series of tethered twistacenes, possessing different degrees of backbone twist, to capture and release singlet oxygen via the reversible Diels-Alder reaction. When the twistacene acts as both a sensitizer and a diene, the photo-oxidation rate depends on the extinction coefficient of the irradiation wavelength. However, when the twistacenes function solely as a diene, the rate of photo-oxidation increases with increasing twist. The rate of the reverse reaction, the singlet oxygen release, also increases with increasing twist. The calculated transition state energy decreases with increasing twist, which can explain the observed trend. The presence of the tether significantly increases the reversibility of the reaction, which can proceed in repeated forward and reverse cycles in very high yield under mild conditions, as required for molecular switches.

Original languageAmerican English
Pages (from-to)7809-7813
Number of pages5
JournalOrganic Letters
Volume22
Issue number20
DOIs
StatePublished - 16 Oct 2020

Bibliographical note

Publisher Copyright:
© 2020 American Chemical Society.

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