PMID- 32418431 OWN - NLM STAT- PubMed-not-MEDLINE DCOM- 20200928 LR - 20200928 IS - 1523-7052 (Electronic) IS - 1523-7052 (Linking) VI - 22 IP - 14 DP - 2020 Jul 17 TI - pH-Controlled Chirality Inversion in Enantiodifferentiating Photocyclodimerization of 2-Antharacenecarboxylic Acid Mediated by gamma-Cyclodextrin Derivatives. PG - 5273-5278 LID - 10.1021/acs.orglett.0c01194 [doi] AB - Several gamma-cyclodextrin (gamma-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 gamma-CDx 7 and its N-methylated derivative 8. FAU - Kanagaraj, Kuppusamy AU - Kanagaraj K AD - Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China. FAU - Liang, Wenting AU - Liang W AD - Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China. AD - Institute of Environmental Science, Shanxi University, Taiyuan 030006, China. FAU - Rao, Ming AU - Rao M AD - Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China. FAU - Yao, Jiabin AU - Yao J AD - Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China. FAU - Wu, Wanhua AU - Wu W AUID- ORCID: 0000-0002-8969-1148 AD - Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China. FAU - Cheng, Guo AU - Cheng G AD - Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China. FAU - Ji, Jiecheng AU - Ji J AD - Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China. FAU - Wei, Xueqin AU - Wei X AD - School of Pharmacy, Guangxi Medical University, Nanning 530021, China. FAU - Peng, Chao AU - Peng C AD - Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China. FAU - Yang, Cheng AU - Yang C AUID- ORCID: 0000-0002-2049-1324 AD - Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China. LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't DEP - 20200517 PL - United States TA - Org Lett JT - Organic letters JID - 100890393 SB - IM EDAT- 2020/05/19 06:00 MHDA- 2020/05/19 06:01 CRDT- 2020/05/19 06:00 PHST- 2020/05/19 06:00 [pubmed] PHST- 2020/05/19 06:01 [medline] PHST- 2020/05/19 06:00 [entrez] AID - 10.1021/acs.orglett.0c01194 [doi] PST - ppublish SO - Org Lett. 2020 Jul 17;22(14):5273-5278. doi: 10.1021/acs.orglett.0c01194. Epub 2020 May 17.