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Molecules 2011, 16(1), 119-148; doi:10.3390/molecules16010119

Solid-State [2+2] Photodimerization and Photopolymerization of α,ω-Diarylpolyene Monomers: Effective Utilization of Noncovalent Intermolecular Interactions in Crystals

Photonics Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Higashi 1-1-1, Tsukuba, Ibaraki 305-8565, Japan
Received: 25 November 2010 / Revised: 17 December 2010 / Accepted: 24 December 2010 / Published: 28 December 2010
(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)
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Abstract

[2+2] Photocycloaddition of olefins is a very useful reaction in synthetic organic chemistry to obtain cyclobutane-containing molecules, which are almost inaccessible by other methods. The reaction, when performed in the crystalline state, occurs more efficiently and selectively than in homogeneous solution due to tight and regular molecular arrangement in the crystal state. Despite numerous examples for the solid-state [2+2] photodimerization of monoenes, however, it is still a challenge to prepare not only dimers but also higher oligomers and polymers from conjugated polyenes, which have multiple reactive double bonds in a molecule. In our recent studies of the solid-state photoreactions of α,ω-diarylpolyenes, noncovalent intermolecular interactions in crystals were effectively utilized to prealign molecules in stacking arrangements, suitable for the [2+2] reaction. With appropriate ring-substituents, [2+2] photodimerization and photopolymerization of the polyenes took place, although the degree of polymerization was relatively low. This review will describe the details of these reactions.
Keywords: ring-substituted diphenylhexatriene; cyclobutane; [2+2] photocycloaddition; hydrogen bond; stacking arrangement ring-substituted diphenylhexatriene; cyclobutane; [2+2] photocycloaddition; hydrogen bond; stacking arrangement
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Sonoda, Y. Solid-State [2+2] Photodimerization and Photopolymerization of α,ω-Diarylpolyene Monomers: Effective Utilization of Noncovalent Intermolecular Interactions in Crystals. Molecules 2011, 16, 119-148.

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