Temperature-Driven Planar Chirality Switching of a Pillar[5]arene-Based Molecular Universal Joint
Jiabin Yao
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Wanhua Wu
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Wenting Liang
Institute of Environmental Sciences, Shanxi University, China
Search for more papers by this authorProf. Yujun Feng
State Key Laboratory of Polymer Materials Engineering, Polymer Research Institute, Sichuan University, China
Search for more papers by this authorDr. Dayang Zhou
Comprehensive Analysis Center, ISIR, Osaka University, Japan
Search for more papers by this authorProf. Jason J. Chruma
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Sino-British Materials Research Institute, College of Physical Sciences & Technology, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorProf. Gaku Fukuhara
Department of Chemistry, Tokyo Institute of Technology, Japan
Search for more papers by this authorProf. Tadashi Mori
Department of Applied Chemistry, Osaka University, Japan
Search for more papers by this authorProf. Yoshihisa Inoue
Department of Applied Chemistry, Osaka University, Japan
Search for more papers by this authorCorresponding Author
Prof. Cheng Yang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorJiabin Yao
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Wanhua Wu
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Wenting Liang
Institute of Environmental Sciences, Shanxi University, China
Search for more papers by this authorProf. Yujun Feng
State Key Laboratory of Polymer Materials Engineering, Polymer Research Institute, Sichuan University, China
Search for more papers by this authorDr. Dayang Zhou
Comprehensive Analysis Center, ISIR, Osaka University, Japan
Search for more papers by this authorProf. Jason J. Chruma
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Sino-British Materials Research Institute, College of Physical Sciences & Technology, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorProf. Gaku Fukuhara
Department of Chemistry, Tokyo Institute of Technology, Japan
Search for more papers by this authorProf. Tadashi Mori
Department of Applied Chemistry, Osaka University, Japan
Search for more papers by this authorProf. Yoshihisa Inoue
Department of Applied Chemistry, Osaka University, Japan
Search for more papers by this authorCorresponding Author
Prof. Cheng Yang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorAbstract
The study of an enantiopure bicyclic pillar[5]arene-based molecular universal joint (MUJ) by single-crystal X-ray diffraction allowed for the first time the unequivocal assignment of the absolute configuration of a planar chiral pillar[5]arene by circular dichroism spectroscopy. Crucially, the absolute configuration of the MUJ was switched reversibly by temperature, with an accompanying sign inversion of the anisotropy factor that varied by as much as 0.03, which is the largest value ever reported. Mechanistically, the reversible chirality switching of the MUJ is driven by the threading/dethreading motion of the fused ring and hence is dependent on both the size and nature of the ring and the solvent employed, reflecting the critical balance between the self-complexation of the ring by pillar[5]arene, the solvation to the excluded ring, and the inclusion of solvent molecules in the cavity.
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