Citation: Jie Yang, Xin-Yue Lou, Dihua Dai, Jingwei Shi, Ying-Wei Yang. Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry[J]. Chinese Chemical Letters, ;2025, 36(1): 109818. doi: 10.1016/j.cclet.2024.109818 shu

Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry

Jie Yang ^{a, b} ,
Xin-Yue Lou ^a ,
Dihua Dai ^a ,
Jingwei Shi ^{c, *,} ,
Ying-Wei Yang ^{a, *,}

a.
College of Chemistry, Jilin University, Changchun 130012, China
b.
School of Life Sciences, Jilin University, Changchun 130012, China
c.
Department of Laboratory Medicine Center, China-Japan Union Hospital of Jilin University, Changchun 130033, China

shijingwei@jlu.edu.cn

ywyang@jlu.edu.cn

Received Date: 30 January 2024
Revised Date: 12 March 2024
Accepted Date: 22 March 2024
Available Online: 24 March 2024

Figures(4)

The preparation, functionalization, and investigations in host-guest properties of high-level pillararene macrocycles have long been a big challenge because of the lack of efficient synthetic methods. Herein, a novel type of pillararene derivative, namely desymmetrized pillar[8]arene (DP[8]A), has been successfully synthesized via a facile two-step strategy with high yield. Compared with its pillar[8]arene counterpart, DP[8]A is composed of four alkoxy-substituted benzene units and four bare benzene rings. Single crystal analysis has been performed in order to unveil the molecular conformation and packing mode of DP[8]A, which indicated that DP[8]A possesses a unique chair-like structure and much smaller steric hindrance. Density functional theory (DFT) calculations and electrostatic potential map suggested the inhomogeneous electronic distribution in the DP[8]A cavity. Water-soluble carboxylate-modified DP[8]A, that is, CDP[8]A, was also prepared to investigate the host-guest properties in aqueous solution with methyl viologen (MV), where the binding constant and morphologies of the formed host-guest complexes have been studied. In all, this new version of eight-membered pillararene derivative might potentially serve as a powerful macrocycle candidate for further applications in supramolecular chemistry.
- Host-guest interaction,
- Macrocycle chemistry,
- Pillararenes,
- Supramolecular chemistry,
- Synthetic macrocycles
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