Issue 48, 2024

Exploring the molecular design principles for efficient diarylethene photoacid and photohydride generators based on the photochemical reaction mechanism

Abstract

Photoacid generators (PAGs) and photohydride generators (PHGs) are specific photolabile protecting groups that release acid and hydride, respectively. Over the past decade, great efforts have been devoted to developing novel PAGs and PHGs with advanced efficiency, among which, two of the promising candidates are diarylethene (DAE)-based PAGs and PHGs, which release acids/hydrides during photochromic electrocyclization. The release quantum yield for PAGs is acceptable, while that of PHGs is only 4.2% even after molecular structure modification. In this work, time-resolved transient absorption spectroscopies with femtosecond and nanosecond resolutions along with DFT/TD-DFT calculations were utilized to unravel the detailed photochemical reaction mechanisms of DAE-based PAGs (1o) and PHGs (2o), respectively. The results show that the different photochemical mechanisms are the key that leads to distinctive release quantum yields between 1o and 2o. The factors affecting the release quantum yield are discussed in detail, and several key design principles are proposed to facilitate future rational design of DAE-based PAGs and PHGs.

Graphical abstract: Exploring the molecular design principles for efficient diarylethene photoacid and photohydride generators based on the photochemical reaction mechanism

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Article information

Article type
Edge Article
Submitted
13 Sep 2024
Accepted
13 Nov 2024
First published
14 Nov 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 20556-20564

Exploring the molecular design principles for efficient diarylethene photoacid and photohydride generators based on the photochemical reaction mechanism

Y. Su, D. Zheng, L. Ge, L. Yu, D. Lee Phillips, J. Ma and Y. Fang, Chem. Sci., 2024, 15, 20556 DOI: 10.1039/D4SC06202G

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