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

DOI: 10.1002/ange.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: $5,250

Funder: Fonds der Chemischen Industrie