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 déc. 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements