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Supramolecular photocyclodimerization of 2-hydroxyanthracene with a chiral hydrogen-bonding template, cyclodextrin and serum albumin.

Photochem Photobiol Sci. 2013 Jun 26;

Authors: Fukuhara G, Umehara H, Higashino S, Nishijima M, Yang C, Mori T, Wada T, Inoue Y


2-Hydroxyanthracene (HA) in its neutral form smoothly photocyclodimerized to four stereoisomeric [4 + 4]-cyclodimers, which were isolated and characterized for the first time, whereas the anionic form of HA turned out to be photochemically inert. Enantiodifferentiating photocyclodimerization of HA in the presence of a chiral hydrogen-bonding template (TKS159), γ-cyclodextrin (γ-CDx) and bovine serum albumin (BSA) was examined to afford chiral syn-head-to-tail and anti-head-to-head cyclodimers in modest enantiomeric excesses with TKS159 and γ-CDx, but practically no photocyclodimerization proceeded in the presence of BSA probably due to the ionization of HA in the binding sites.

PMID: 23801196 [PubMed - as supplied by publisher]