Citation: Fanrui Gao, Xingke Yu, Ling Liu, Jinlei Chen, Yongjun Lv, Ting Zhao, Jiecheng Ji, Jiabin Yao, Wanhua Wu, Cheng Yang. Chiroptical switching of molecular universal joint triggered by complexation/release of a cation: A stepwise synergistic complexation[J]. Chinese Chemical Letters, ;2023, 34(2): 107558. doi: 10.1016/j.cclet.2022.05.072 shu

Chiroptical switching of molecular universal joint triggered by complexation/release of a cation: A stepwise synergistic complexation

Fanrui Gao ^{a, 1} ,
Xingke Yu ^{a, 1} ,
Ling Liu ^a ,
Jinlei Chen ^a ,
Yongjun Lv ^a ,
Ting Zhao ^a ,
Jiecheng Ji ^a ,
Jiabin Yao ^{b, *,} ,
Wanhua Wu ^{a, *,} ,
Cheng Yang ^{a, *,}

a.
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
b.
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China

yaojiabin47@163.com

wuwanhua@scu.edu.cn

yangchengyc@scu.edu.cn

Received Date: 21 April 2022
Revised Date: 22 May 2022
Accepted Date: 23 May 2022
Available Online: 27 May 2022

Figures(6)

Pillar[5]arene-based molecular universal joints (MUJs), bearing fused crown ether subring (MUJ1 and MUJ3) or a ring without ether oxygen atom (MUJ2), were synthesized and enantio‑differentiated. Significant chiral inversion was observed for the crown ether-fused MUJs upon the addition of equivalent cations Na⁺, showing an anisotropy (g) factor of 0.014, while alkyl subring-fused MUJ2 showed no CD inversions. Unprecedentedly, sodium ion triggered rolling-in motion of the subring to the pillar[5]arene cavity was verified, and the synergistic noncovalent interaction of cation-π interactions and CH···π interactions were responsible for the stabilized self-included conformers. The addition of MeOH or competitive hosts 15-crown-5 ether disassembled the complex of MUJ1 and Na⁺ followed by a rolling-out of the subring, which made the sodium-ion triggered chiroptical switching reversible.
- Molecular universal joint,
- Chiroptical switching,
- Host-guest interaction,
- Pillar[5]arene,
- Synergistic complexing
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