Work

Switching Sides: Regiochemistry and Functionalization Dictate the Photoswitching Properties of Imines

Year: 2024

Type: article

Abstract: Photoswitchable imines demonstrate light-dependent dynamic covalent chemistry and can function as molecular ratchets. However, the design of aryliminopyrazoles (AIPs) has been limited to N-pyrazole derivatives with ortho-pyrrolidine motifs. The impact of other functionalization patterns on the photoswitching properties remains unknown. Here, we present a systematic structure-property analysis and study how the photoswitching properties can be tuned through ortho- and para-functionalization of the phenyl ring in N-pyrazole and N-phenyl AIPs. This study establishes the first set of design rules for these AIP photoswitches and reports the most stable Z-isomer of an AIP to date, enabling its crystallization and resulting in the first reported crystal structure of a metastable Z-aldimine. Finally, we demonstrate that the AIPs are promising candidates for photoswitching in the condensed phase.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202415464

Authors: Jiarong Wu, Lasse Kreimendahl, Jake L. Greenfield

Institution: University of Würzburg

Language: English

Topic: Photochromic and Fluorescence Chemistry

Subfield: Materials Chemistry

Field: Materials Science

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funder: Fonds der Chemischen Industrie