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Competitive isomerization and dimerization in co-crystals of 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol and sorbic acid: A new look at stereochemical requirements for [2+2] dimerization

par Zheng, Shao-Liang;Pham, Oanh;Vande Velde, Christophe ;Gembicky, Milan;Coppens, Philip
Référence Chemical communications, 22, page (2538-2540)
Publication Publié, 2008

Article révisé par les pairs

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Résumé :

Competitive [2+2] photodimerization and E→Z isomerization reactions occur in a co-crystal of 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol upon irradiation with 325 nm light. At 90 K both reactions are observed, whereas at 280 K the dimerization reaction is very fast and inhibits isomerization as the nature of the chromophore is affected by the reaction. The temperature dependence of the stereospecificity of the dimerization reaction is related to the large sliding motion required to bring the reacting molecules into juxtaposition. The progress of the reactions has been monitored by photocrystallographic methods. © The Royal Society of Chemistry.