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pH-Controlled Chirality Inversion in Enantiodifferentiating Photocyclodimerization of 2‑Antharacenecarboxylic Acid Mediated by γ‑Cyclodextrin Derivatives

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journal contribution
posted on 18.05.2020, 04:13 authored by Kuppusamy Kanagaraj, Wenting Liang, Ming Rao, Jiabin Yao, Wanhua Wu, Guo Cheng, Jiecheng Ji, Xueqin Wei, Chao Peng, Cheng Yang
Several γ-cyclodextrin (γ-CDx) derivatives were used as chiral hosts for the photocyclodimerization of 2-anthracenecarboxylic acid (AC). The effect of pH on photoreactivity and stereochemical outcome of photoproducts was investigated. Upon changing the solution pH, the stereochemical outcome of HH cyclodimer 3 was inverted from 25.2% to −64.4% and 41.2% to −76.2%, respectively, in the photocyclodimerization of AC mediated by bis-quinoline-modified γ-CDx 7 and its N-methylated derivative 8.