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

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‐catalyze...

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Published in:Angewandte Chemie International Edition Vol. 61; no. 42; pp. e202211853 - n/a
Main Authors: Wang, Yan‐Fang, Yao, Huan, Yang, Liu‐Pan, Quan, Mao, Jiang, Wei
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 17.10.2022
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
Alcohols
binding capacity
Cations
Chemical reactions
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Chirality
Chirality Sensing
Conformation
Friedel-Crafts reaction
Holes
Homology
Host–Guest Chemistry
Macrocycles
macrocyclic compounds
Methylene
Molecular Conformation
Molecular Recognition
Naphthotubes
optical isomerism
Physical Sciences
Recognition
Science & Technology
Host-Guest Chemistry
BIS-NAPHTHALENE
Naphthotubes
Chirality Sensing
CAVITY
COMPLEXES
Macrocycles
Molecular Recognition
MACROCYCLIC HOSTS
CALIXARENES
FAMILY
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Summary: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 108 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. Methylene‐bridged naphthotubes have been successfully developed. The three‐membered naphthotubes possess a rigid and well‐defined cavity, while four‐membered naphthotubes possess a double‐cavity conformation or a self‐filling conformation depending on the alkoxy length. They show quite strong binding affinities (up to 108 M−1) to organic cations and can be used as chirality sensors for chiral organic cations.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202211853