A Triple-Stimuli-Responsive Photolabile Protecting Group Platform for Controlled Release

Photolabile protecting groups (PPGs) enable spatiotemporal control of chemical and biological processes, yet multistimuli-regulated systems remain rare. Here we report a triple-stimuli platform integrating light, base, and acid to control PPG release. Photoirradiation of diarylethenes (DAEs) under basic conditions generates stable 9,10-dihydrophenanthrene (9,10-DHP) intermediates that activate hemiaminal ethers and undergo acid-promoted aromatization to release the alcohol group. Distinct fluorescence changes allow real-time monitoring in both organic and aqueous media.

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Publication Details

Journal
Organic Letters
Published
2026-05-02
DOI
https://doi.org/10.1021/acs.orglett.6c01180
Primary Topic
Photochromic and Fluorescence Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

A Triple-Stimuli-Responsive Photolabile Protecting Group Platform for Controlled Release

Hebo Ye, Lei You, Guoshan Jiang, J Huang et al.
Organic Letters
Photochromic and Fluorescence Chemistry
article

A Triple-Stimuli-Responsive Photolabile Protecting Group Platform for Controlled Release

Hebo Ye, Lei You, Guoshan Jiang, J Huang, Long Wang
article en

Abstract

Photolabile protecting groups (PPGs) enable spatiotemporal control of chemical and biological processes, yet multistimuli-regulated systems remain rare. Here we report a triple-stimuli platform integrating light, base, and acid to control PPG release. Photoirradiation of diarylethenes (DAEs) under basic conditions generates stable 9,10-dihydrophenanthrene (9,10-DHP) intermediates that activate hemiaminal ethers and undergo acid-promoted aromatization to release the alcohol group. Distinct fluorescence changes allow real-time monitoring in both organic and aqueous media.

Organic Letters
Fujian Normal University (CN), Chinese Academy of Sciences (CN), Material (Belgium) (BE), Fujian Institute of Research on the Structure of Matter (CN), Tan Kah Kee Innovation Laboratory (CN), University of Chinese Academy of Sciences (CN)
National Natural Science Foundation of China, Chinese Academy of Sciences, Natural Science Foundation of Fujian Province, Fujian Science and Technology Innovation Laboratory for Optoelectronic Information of China
Openalex Percentile: Top 15%
Photochromic and Fluorescence Chemistry
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