Issue 5, 2021

Photoreactive salt cocrystal: N+–H⋯N hydrogen bond and cation–π interactions support a cascade-like photodimerization of a 4-stilbazole

Abstract

We describe hydrogen bonds (i.e., N+–H⋯N) in combination with cation⋯π interactions to enable a cascade-like [2 + 2] photodimerization of 4-stilbazole in a salt cocrystal. A four-component crystal assembly is composed of photoactive pyridinium ion pair 4-stilbzH+ (4-stilbz = trans-1-(4-pyridyl)-2-(phenyl)ethylene) and photostable molecule pair 4-stilbz. UV irradiation gives rctt-1,2-bis(4-pyridyl)-3,4-bis(phenyl)cyclobutane (4-pyr-ph-cb) in quantitative yield. An intermediate structure 2(4-stilbz)·(4-pyr-ph-cb)2H+ is isolated that undergoes a partial single-crystal-to-single-crystal transformation. The single-crystal X-ray data provides a snapshot of movements in the salt cocrystal in the course of the photodimerization.

Graphical abstract: Photoreactive salt cocrystal: N+–H⋯N hydrogen bond and cation–π interactions support a cascade-like photodimerization of a 4-stilbazole

Supplementary files

Article information

Article type
Communication
Submitted
30 Dec. 2020
Accepted
18 Janv. 2021
First published
21 Janv. 2021

CrystEngComm, 2021,23, 1071-1074

Author version available

Photoreactive salt cocrystal: N+–H⋯N hydrogen bond and cation–π interactions support a cascade-like photodimerization of a 4-stilbazole

C. Li, G. Campillo-Alvarado, D. C. Swenson and L. R. MacGillivray, CrystEngComm, 2021, 23, 1071 DOI: 10.1039/D0CE01885F

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