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Effect of thiophene substitution on the intersystem crossing of arene photosensitizers

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Abstract

The effect of thienyl substitution on the intersystem crossing (ISC) of a few arenes was studied using steady state and time-resolved transient absorption and emission spectroscopies, as well as DFT/TDDFT computations. We found that the phenyl and thienyl substituents generally induce red-shifted absorptions for the chromophores, and the DFT/TDDFT computations show that the red-shifted absorption and emission are due to the increased HOMO and the reduced LUMO energy levels. Nanosecond transient absorption spectra indicate the formation of a triplet state, the triplet state lifetime is up to 282 μs, and the singlet oxygen quantum yields (ΦΔ) are up to 60%. DFT/TDDFT computations indicate that introducing the thienyl substituent alters the relative singlet/triplet excited state energy levels, and the energy level-matched S1/T2 states are responsible for the enhanced ISC of the thienyl compounds. This information is useful for the design of heavy atom-free triplet photosensitizers and for the study of the fundamental photochemistry of organic compounds.

Graphical abstract: Effect of thiophene substitution on the intersystem crossing of arene photosensitizers

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Publication details

The article was received on 05 Jun 2018, accepted on 21 Aug 2018 and first published on 21 Aug 2018


Article type: Paper
DOI: 10.1039/C8PP00230D
Citation: Photochem. Photobiol. Sci., 2018, Advance Article
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    Effect of thiophene substitution on the intersystem crossing of arene photosensitizers

    F. Sadiq, J. Zhao, M. Hussain and Z. Wang, Photochem. Photobiol. Sci., 2018, Advance Article , DOI: 10.1039/C8PP00230D

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