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Enhancing the Photoswitching Properties of <i>N</i>-Alkyl Imines

Jiarong Wu, Lasse Kreimendahl, Jake L. Greenfield

2025Journal of the American Chemical Society19 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide 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.

Topics & Concepts

ChemistryAlkylNanotechnologyOrganic chemistryMaterials sciencePhotochromic and Fluorescence ChemistryPhotoreceptor and optogenetics researchMolecular Sensors and Ion Detection
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