Photoreactive Polymorphic Cocrystals Utilizing a Molecular Template with Dual Halogen and Hydrogen Bonding Capabilities

The ability of 1,2,4,5-tetrachloro-3-iodobenzene to act as a template to form a pair of polymorphic cocrystals with trans-1,2-bis­(4-pyridyl)­ethylene is reported. After exposure to ultraviolet light, a nearly quantitative yield for the [2 + 2] cycloaddition reaction was observed for both concomitan...

Full description

Saved in:
Bibliographic Details
Published in:Crystal growth & design 2023-06, Vol.23 (6), p.3947-3951
Main Authors: Bosch, Eric, Powell, Conrad J., Krueger, Herman R., Groeneman, Ryan H.
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The ability of 1,2,4,5-tetrachloro-3-iodobenzene to act as a template to form a pair of polymorphic cocrystals with trans-1,2-bis­(4-pyridyl)­ethylene is reported. After exposure to ultraviolet light, a nearly quantitative yield for the [2 + 2] cycloaddition reaction was observed for both concomitant cocrystals. These crystalline solids engage in both I···N halogen bonds along with nontraditional C–H···N hydrogen bond which results in a one-dimensional chain. In addition, the components homogeneous π–π stack which positions the carbon–carbon double bond on the reactant molecule in a suitable orientation to undergo a photoinduced cyclization reaction.
ISSN:1528-7483
1528-7505
DOI:10.1021/acs.cgd.3c00304