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Enhancing the photoswitching properties of N-alkyl imines

Jiarong Wu, Lasse Kreimendahl, Jake L. Greenfield*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

N-Alkyl imines are prevalent in dynamic-covalent chemistry and self-assembled structures, yet their E/Z photochromism is often overlooked due to the high-energy light required for isomerization. Here, we present a simple strategy to enhance their photoswitching properties, achieving switching wavelengths and photostationary state distributions comparable to azobenzene. Moreover, we demonstrate that these N-alkyl imines undergo photoisomerization in the condensed phase and exhibit isomer-dependent fluorescence. We anticipate that this study will inspire the design of photoresponsive architectures that operate directly at the dynamic-covalent bond, eliminating the need for dedicated photoswitchable motifs.
Original languageEnglish
Pages (from-to)17549-17554
Number of pages6
JournalJournal of the American Chemical Society
Volume147
Issue number21
Early online date15 May 2025
DOIs
Publication statusPublished - 28 May 2025

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