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Head-to-tail and head-to-head [2+2] photodimerization of an unsymmetrical olefin containing benzimidazole and pyridyl groups was achieved by irradiating Ag(I) complexed olefin in crystalline state and gel state, respectively, in stereoselective manner. The [2+2] reaction indicates that the molecular arrangement in a gel is different from that of a xerogel.

Graphical abstract: Does crystal or gel matter to stereochemistry of a reaction? Silver complexation-promoted solid-state [2+2] reaction of an unsymmetrical olefin

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