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.
|Number of pages||10|
|Journal||Photochemical and Photobiological Sciences|
|Publication status||Published - 2014 Feb|
ASJC Scopus subject areas
- Physical and Theoretical Chemistry