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Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid via competitive binary/ternary
Yuko Kawanami1, Shin-ya Katsumata, Jun-ichi Mizoguchi
1Department of Applied Chemistry, Osaka University, 2-1 Yamadaoka, Suita 565-0871, Japan.
Abstract:
Circular dichroism (CD) spectral examinations at various host/guest ratios revealed that 2-anthracenecarboxylic acid (AC) forms not only 1:1 but also novel 2:1 hydrogen-bonded/π-stacked complexes with a chiral 4-benzamidoprolinol template (TKS159). The 2:1 complexation is a minor process but causes significant CD spectral changes as a consequence of the exciton coupling interaction of two AC chromophores and greatly accelerates the head-to-head photocyclodimerization to significantly affect the stereochemical outcomes.
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