Citation: Caihong Mao, Yanfeng He, Xiaohan Wang, Yan Cai, Xiaobo Hu. Synthesis and molecular recognition characteristics of a tetrapodal benzene cage[J]. Chinese Chemical Letters, ;2024, 35(8): 109362. doi: 10.1016/j.cclet.2023.109362 shu

Synthesis and molecular recognition characteristics of a tetrapodal benzene cage

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua 321004, China

xiaobo.hu@zjnu.edu.cn

Received Date: 14 September 2023
Revised Date: 22 November 2023
Accepted Date: 3 December 2023
Available Online: 5 December 2023

Figures(6)

In this contribution, we describe the preparation and recognition characteristics of a novel tetrapodal benzene cage (1). The cage can express a wide recognition range without losing selectivity for the object of appropriate size and functional groups. The key to obtaining the desired structural isomer of 1 is the synthesis and isolation of the o-bis(bromomethyl)benzene precursor (5). Three distinct guests, F⁻ (extremely small size), D-lactate (appropriate size) and L-Asp (branched shape), were selected as examples to demonstrate the recognition characteristics of 1. By NMR titration studies, they all expressed good binding affinity (K > 10⁵ L/mol) in competitive medium (10% DMSO/THF), indicating that 1 has a wide recognition scope. The highest binding constant was observed for D-lactate, revealing that 1 has good selectivity for D-lactate versus F⁻ and L-Asp. Moreover, the NMR titration study of F⁻ in DMSO indicates 1 can achieve different binding modes (1:1 and 2:1 guest-host) for small-sized guests, which allows for the further development of binary binding properties and thereafter applications in the field of catalysis.
- Cage molecules,
- Host-guest chemistry,
- Multi-step organic synthesis,
- D-Lactate recognition,
- L-Asp recognition
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