A shape-persistent arylene ethynylene macrocycle with a multiple acetamide modified cavity: synthesis and gelation
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-depend...
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Veröffentlicht in: | Soft matter 2021-03, Vol.17 (11), p.3242-3249 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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
1
HNMR 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 Hg
2+
. 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.
Strong H-bonds suppress π-π stacking leading to an AIEE gel from a planar conjugated macrocycle. |
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ISSN: | 1744-683X 1744-6848 |
DOI: | 10.1039/d0sm02144j |