Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Photoreaction of 1,4-Diphenyl-1,3-butadiyne and 1,4-Di-t-butyl-1,3-butadiyne with Some Olefins

  • Published : 1985.06.20
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Abstract

A diacetylene compound, 1,4-diphenyl-1,3-butadiyne, was photolyzed with 2,3-dimethyl-2-butene, 1,4-cyclohexadiene, dimethyl fumarate, and methyl crotonate, as a model reaction of the phototoxic conjugated polyynes with DNA or RNA and [2 + 2] photocycloadducts were obtained except for 1,4-cyclohexadiene. In the photoreaction of 1,4-diphenyl-1,3-butadiyne with 2,3-dimethyl-2-butene, a [2 + 2 + 2] photoadduct was additionally obtained. The photolysis of 1,4-di-t-buyl-1,3-butadiyne with 2,3-dimethyl-2-butene also yielded a [2 + 2] photoadduct. Fluorescence was observed from all the photoadducts while the reactants did not show any fluorescence.

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  1. Unique interplay between electronic states and dihedral angle for the molecular rotor diphenyldiacetylene vol.13, pp.36, 1985, https://doi.org/10.1039/c0cp02914a