2020 Redox‐Triggered Chirality Switching and Guest‐Capture/Release with a Pillar[6]arene‐Based Molecular Universal Joint

Authors:
Chao Xiao, Prof. Wanhua Wu, Prof. Wenting Liang, Prof. Dayang Zhou, Dr. Kuppusamy
Kanagaraj, Prof. Guo Cheng, Prof. Dan Su, Prof. Zhihui Zhong, Prof. Jason J. Chruma, Prof. Cheng Yang

Journal:
Angewandte Chemie, 20 January, 2020, DOI: 10.1002/ange.201916285

Institut:

C. Xiao, Prof. W. Wu, Dr. K. Kanagaraj, Prof. G. Chen, Prof. D. Su, Prof. Z. Zhong, Prof. J. J. Chruma and Prof. C. Yang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, State Key Laboratory of Biotherapy, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064 (China)

Prof. W. Liang
Institute of Environmental Sciences, Shanxi University (China)

Prof. D. Zhou
Comprehensive Analysis Center, ISIR, Osaka University (Japan)

Abstract:

A chiral electrochemically responsive molecular universal joint (EMUJ) was synthesized by fusing a macrocyclic pillar[6]arene (P[6]) to a ferrocene‐based side ring. A single crystal of an enantiopure EMUJ was successfully obtained, which allowed, for the first time, the definitive correlation between the absolute configuration and the circular dichroism spectrum of a P[6] derivative to be determined. The self‐inclusion and self‐exclusion conformational change of the EMUJ led to a chiroptical inversion of the P[6] moiety, which could be manipulated by both solvents and changes in temperature. The EMUJ also displayed a unique redox‐triggered reversible in/out conformational switching, corresponding to an occupation/voidance switching of the P[6] cavity, respectively. This phenomenon is an unprecedented electrochemical manipulation of the capture and release of guest molecules by supramolecular hosts.