Issue 11, 2021

A shape-persistent arylene ethynylene macrocycle with a multiple acetamide modified cavity: synthesis and gelation

Abstract

A new arylene ethynylene macrocycle (AEM) molecule bearing endo-acetamide groups was obtained by a Pd/Cu mediated homo-coupling reaction. Introducing tetraethylene glycol ether as a linkage between two C-shaped fragments substantially improved the final cyclization yield (30%). Concentration-dependent 1HNMR experiments indicated that strong aggregates formed through H-bonds were observed for this new macrocycle with amide groups in solution. And also, this macrocycle was fluorescent in solution and showed a highly selective fluorescence quenching response toward the highly toxic Hg2+. More importantly, this macrocycle could induce gelation of several solvents. Significantly, an interesting aggregation-induced enhanced emission (AIEE) behavior was observed for this macrocycle upon gelation. Both SEM and TEM investigations revealed that nanoporous structures existed in the xerogels. This study offers a new molecular design approach to develop fluorescent gels from planar AEM molecules with a functional cavity.

Graphical abstract: A shape-persistent arylene ethynylene macrocycle with a multiple acetamide modified cavity: synthesis and gelation

Supplementary files

Article information

Article type
Paper
Submitted
03 Dec 2020
Accepted
08 Feb 2021
First published
09 Feb 2021

Soft Matter, 2021,17, 3242-3249

A shape-persistent arylene ethynylene macrocycle with a multiple acetamide modified cavity: synthesis and gelation

Y. Ruan, Q. Li, L. Shu and J. Wan, Soft Matter, 2021, 17, 3242 DOI: 10.1039/D0SM02144J

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