Synthesis and molecular recognition characteristics of a tetrapodal benzene cage  

作　　者：Caihong Mao Yanfeng He Xiaohan Wang Yan Cai Xiaobo Hu 

机构地区：[1]Key Laboratory of the Ministry of Education for Advanced Catalysis Materials,College of Chemistry and Materials Science,Zhejiang Normal University,Jinhua 321004,China

出　　处：《Chinese Chemical Letters》2024年第8期240-244,共5页中国化学快报（英文版）

基　　金：support by the National Natural Science Foundation of China(No.22101260);Natural Science Foundation of Zhejiang Province(No.LQ22B020001).

摘　　要：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^(−)(ex-tremely 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>10^(5) 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.

关 键 词：Cage molecules Host-guest chemistry Multi-step organic synthesis d-Lactate recognition l-Asp recognition 

分 类 号：O641.3[理学—物理化学] O623.651[理学—化学]