A shape-persistent arylene ethynylene macrocycle with a multiple acetamide modified cavity: synthesis and gelation
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Updated: Nov 16, 2025

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
Yang Ruan1, Qian-Hui Li, Lijin Shu
1Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, 310012, P. R. China. wan_junhua@hznu.edu.cn shulj@hznu.edu.cn.
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.
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