Citation: Yi Jigao, Liang Wenting, Wei Xueqin, Yao Jiabin, Yan Zhiqiang, Su Dan, Zhong Zhihui, Gao Guowei, Wu Wanhua, Yang Cheng. Switched enantioselectivity by solvent components and temperature in photocyclodimerization of 2-anthracenecarboxylate with 6^A, 6^X-diguanidio-γ-cyclodextrins[J]. Chinese Chemical Letters, ;2018, 29(1): 87-90. doi: 10.1016/j.cclet.2017.05.004 shu

Switched enantioselectivity by solvent components and temperature in photocyclodimerization of 2-anthracenecarboxylate with 6^A, 6^X-diguanidio-γ-cyclodextrins

Yi Jigao ^a ,
Liang Wenting ^b ,
Wei Xueqin ^a ,
Yao Jiabin ^a ,
Yan Zhiqiang ^a ,
Su Dan ^a ,
Zhong Zhihui ^a ,
Gao Guowei ^a ,
Wu Wanhua ^a,, ,
Yang Cheng ^a,,

a.
Key Laboratory of Green Chemistry & Technology, College of Chemistry and State Key Laboratory of Biotherapy, West China Medical Center, Sichuan University, Chengdu 610064, China
b.
Institute of Environmental Sciences, Department of Chemistry, Shanxi University, Taiyuan 030006, China

Corresponding author: Wu Wanhua, wuwanhua@scu.edu.cn Yang Cheng, yangchengyc@scu.edu.cn; yangcheng30@hotmail.com
Received Date: 6 March 2017
Revised Date: 17 April 2017
Accepted Date: 20 April 2017
Available Online: 11 January 2017

Figures(2)

A series of 6^A, 6^X-diguanidio-γ-cyclodextrins (CDs) were used as chiral hosts for mediating the enantiodifferentiating[4 + 4] photocyclodimerization of 2-anthracenecarboxylic acid (AC). These γ-CD derivatives form stable 1:2 ternary complexes with AC in aqueous ammonia solutions and the head-tohead photodimers 3 and 4 were greatly enhanced in the presence of these diguanidio-γ-CDs. The enantioselectivity of chiral photodimers 2 and 3 is a critical function of the temperature and the ammonia contents, showing inverted product chirality by changing these external factors.
- Cyclodextrins,
- Photocyclodimerization,
- Anthracenecarboxylic acid,
- Supramolecular complexation,
- Solvent effect
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Switched enantioselectivity by solvent components and temperature in photocyclodimerization of 2-anthracenecarboxylate with 6A, 6X-diguanidio-γ-cyclodextrins

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通讯作者: 陈斌, bchen63@163.com

Switched enantioselectivity by solvent components and temperature in photocyclodimerization of 2-anthracenecarboxylate with 6^A, 6^X-diguanidio-γ-cyclodextrins