Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan.
Photochem Photobiol Sci. 2014 Feb;13(2):162-71. doi: 10.1039/c3pp50127b.
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.
2-羟基蒽（HA）在中性形式下可顺利地光环二聚化生成四个立体异构的[4+4]-环二聚体，这些环二聚体首次被分离和表征，而 HA 的阴离子形式则表现出光化学惰性。在手性氢键模板（TKS159）、γ-环糊精（γ-CDx）和牛血清白蛋白（BSA）的存在下，对 HA 的对映选择性光环二聚化进行了研究，结果在 TKS159 和 γ-CDx 的存在下，以中等对映过量值得到了手性顺式-头对头和反式-头对头环二聚体，但在 BSA 存在下，光环二聚化几乎没有进行，这可能是由于 HA 在结合部位发生了离子化。
