Journal article
Photoreactive salt cocrystal: N+–H⋯N hydrogen bond and cation–π interactions support a cascade-like photodimerization of a 4-stilbazole
CrystEngComm, Vol.23(5), pp.1071-1074
02/09/2021
DOI: 10.1039/D0CE01885F
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.
Details
- Title: Subtitle
- Photoreactive salt cocrystal: N+–H⋯N hydrogen bond and cation–π interactions support a cascade-like photodimerization of a 4-stilbazole
- Creators
- Changan Li - Department of Chemistry, University of Iowa, Iowa City, USAGonzalo Campillo-Alvarado - Department of Chemistry, University of Iowa, Iowa City, USADale C Swenson - Department of Chemistry, University of Iowa, Iowa City, USALeonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, USA
- Resource Type
- Journal article
- Publication Details
- CrystEngComm, Vol.23(5), pp.1071-1074
- DOI
- 10.1039/D0CE01885F
- ISSN
- 1466-8033
- eISSN
- 1466-8033
- Grant note
- DOI: 10.13039/100000078, name: Division of Materials Research, award: DMR-1708673
- Language
- English
- Date published
- 02/09/2021
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216616702771
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