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Polymorphism in a trans-cinnamic acid derivative exhibiting two distinct β‑type phases: structural properties, [2 + 2] photodimerization reactions, and polymorphic phase transition behavior

Khoj, Manal A., Hughes, Colan Evan, Harris, Kenneth David Maclean and Kariuki, Benson 2013. Polymorphism in a trans-cinnamic acid derivative exhibiting two distinct β‑type phases: structural properties, [2 + 2] photodimerization reactions, and polymorphic phase transition behavior. Crystal Growth and Design 13 (9) , pp. 4110-4117. 10.1021/cg4009202

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Abstract

We report the discovery of a rare case of polymorphism among trans-cinnamic acid derivatives in which both polymorphs are classified as β-type structures based on their solidstate structural properties and their solid-state photoreactivity. Specifically, for 3-fluoro-transcinnamic acid, crystallization from many solvent systems leads to formation of one polymorph (denoted β1), although, in a few cases, concomitant crystallization of another polymorph (denoted β2) is also observed. On heating the β1 polymorph, a solid-state phase transition occurs at ca. 119 °C to produce the β2 polymorph. This polymorphic phase transition is irreversible, and the β2 polymorph remains stable on subsequent cooling to ambient temperature. Both the β1 and the β2 polymorphs undergo a topochemical [2 + 2] photodimerization reaction upon UV irradiation to produce 3,3′- difluoro-β-truxinic acid as the photoproduct in almost 100% yield. However, these reactions are associated with complete loss of crystallinity, preventing the structural properties of the directly produced solid photoproduct from being determined by singlecrystal or powder X-ray diffraction techniques.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 1528-7483
Last Modified: 04 Jun 2017 05:18
URI: http://orca.cf.ac.uk/id/eprint/50578

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