Synthesis, Configurational Analysis, Molecular Recognition and Chirality Sensing of Methylene-Bridged Naphthotubes

Wang, Yan-Fang1,2; Yao, Huan1,2; Yang, Liu-Pan1,2; Quan, Mao1,2; Jiang, Wei1,2

2022-09-01

10.1002/anie.202211853

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

Macrocyclic hosts with a well-defined cavity are particularly appealing for supramolecular chemistry, but they are still rare. In this research, we reported a new class of macrocyclic hosts, namely methylene-bridged naphthotubes, with well-defined cavities. They were synthesized through TFA-catalyzed Friedel-Crafts reactions between alkoxy-substituted bisnaphthalenes and paraformaldehyde. A configurational selection was observed. Three-membered macrocycles possess a single cavity, while four-membered macrocycles adopt a double-cavity conformation or a self-filling conformation depending on the alkoxy length. The small homologue shows quite strong binding affinities (up to 10(8) M-1) to organic cations, which is better than structurally similar but flexible macrocycles. This demonstrates the advantage of a well-defined cavity in molecular recognition. Moreover, these naphthotubes can be used as chirality sensors for chiral organic cations through different chirality transfer mechanisms.

Chirality Sensing Host-Guest Chemistry Macrocycles Molecular Recognition Naphthotubes

SCI ; EI

英语

NI论文

第一 ; 通讯

National Natural Science Foundation of China["22125105","22101125"] ; Shenzhen Science and Technology Innovation Committee[JCYJ20180504165810828] ; Shenzhen "Pengcheng Scholar", Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Guangdong HighLevel Personnel of Special Support Program[2019TX05C157]

Chemistry

Chemistry, Multidisciplinary

WOS:000853132800001

WILEY-V C H VERLAG GMBH

20223812749407

Acetal resins ; Binding energy ; Conformations ; Molecular recognition ; Positive ions ; Stereochemistry

Chemistry:801 ; Physical Chemistry:801.4 ; Organic Polymers:815.1.1 ; Atomic and Molecular Physics:931.3

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen Grubbs Inst, Xueyuan Blvd 1088, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Xueyuan Blvd 1088, Shenzhen 518055, Peoples R China

Wang, Yan-Fang,Yao, Huan,Yang, Liu-Pan,et al. Synthesis, Configurational Analysis, Molecular Recognition and Chirality Sensing of Methylene-Bridged Naphthotubes[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2022.

Wang, Yan-Fang,Yao, Huan,Yang, Liu-Pan,Quan, Mao,&Jiang, Wei.(2022).Synthesis, Configurational Analysis, Molecular Recognition and Chirality Sensing of Methylene-Bridged Naphthotubes.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.

Wang, Yan-Fang,et al."Synthesis, Configurational Analysis, Molecular Recognition and Chirality Sensing of Methylene-Bridged Naphthotubes".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022).