With three examples, we have established that cis-cinnamic acids can dimerize via a diradical intermediate in the crystalline state provided that the intermolecular distance is less than 4.2 Å. In the excited state of cis-isomers, C–C bond formation with an adjacent molecule competes with geometric isomerization.
![Graphical abstract: Solid-state photochemistry of cis-cinnamic acids: a competition between [2 + 2] addition and cis–trans isomerization](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C6CE00682E&imageInfo.ImageIdentifier.Year=2016)
G. B. Veerakanellore, B. Captain and V. Ramamurthy, CrystEngComm, 2016, 18, 4708 DOI: 10.1039/C6CE00682E
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