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Photochem Photobiol Sci. 2019 May 15;18(5):989-992. doi: 10.1039/c9pp00004f.

Regioselective photoreactions within a series of mixed co-crystals containing isosteric dihalogenated resorcinols with 4-stilbazole.

Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology

Anna L Grobelny, Nigam P Rath, Ryan H Groeneman

Affiliations

  1. Department of Biological Sciences, Webster University, 470 East Lockwood Ave., St. Louis, MO 63119, USA. [email protected].

PMID: 30849166 DOI: 10.1039/c9pp00004f

Abstract

The formation and photoreactivity of a series of mixed co-crystals containing 4-stilbazole along with both 4,6-dichlororesorcinol and 4,6-dibromoresorcinol at various ratios is reported. In all cases, the quantitative [2 + 2] cycloaddition reaction yields an identical head-to-tail photoproduct, namely rctt-1,3-bis(4-pyridyl)-2,4-bis(phenyl)cyclobutane. The selectivity in the cycloaddition reaction occurred due to a shorter distance observed between two carbon-carbon double bonds that were found between and not within the hydrogen-bonded assemblies.

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