Regiospecific [2 + 2] photocyclodimerization of trans-4-styrylpyridines templated by cucurbit[8]uril

Asao Nakamura, Hiromi Irie, Shuhei Hara, Mai Sugawara, Shinji Yamada

研究成果: Article査読

26 被引用数 (Scopus)


Addition of HCl accelerated the photocyclodimerization of trans-4-styrylpyridine 1a in methanol and increased the yield of syn-head-to-tail (syn-HT) dimer 2a through the effect of cation-π interactions between the pyridinium ion of one molecule and the phenyl group of the other. We examined the photoirradiation products of derivatives of 1a having alkyl substituents on the phenyl group (1b-1f). The effect of the alkyl substituent on product distribution was rather limited for the photoreaction in MeOH solutions. However, the substituents had a distinct effect on the product distribution for the photoreaction of the inclusion complexes of hydrochloride salts of trans-4-styrylpyridines with cucurbit[8]uril in aqueous solutions. Introducing an alkyl group at the 2- or 3-position of the phenyl group completely shifted the major product from the syn-HT dimer to the syn-head-to-head (syn-HH) dimer. By adjusting the balance of host-guest interactions and cation-π interactions between guest molecules through systematic changes in the substituents on the phenyl ring of trans-4-styrylpyridine, we could change the orientation of the reactant molecules in the host cavity, resulting in a change of the major regioisomer of the photocyclodimerization products.

ジャーナルPhotochemical and Photobiological Sciences
出版ステータスPublished - 2011 9月

ASJC Scopus subject areas

  • 物理化学および理論化学


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