期刊
MACROMOLECULES
卷 54, 期 17, 页码 7840-7848出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.macromol.1c00938
关键词
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资金
- National Science Foundation [CHE-1808234, DMR-1644779]
- State of Florida
- NIH [S10 RR031637]
This study reports the synthesis of cyclic polyacetylene through ring-expansion metathesis polymerization of cyclic alkenes and subsequent retro-Diels-Alder elimination. Characterizations of the polymer precursors confirmed their cyclic structure, leading to the successful fabrication of semiconducting films.
Cyclic polyacetylene (c-PA) is the cyclic derivative of the semiconducting linear polyacetylene. As with the linear derivative, cyclic polyacetylene is insoluble, making its characterization and processing challenging. Herein, we report the synthesis of c-PA via an indirect approach, employing ring-expansion metathesis polymerization of cyclic alkenes to form soluble polymer precursors. Subsequent retro-Diels-Alder elimination through heating provides c-PA. Dilute solution characterizations of the polymer precursors including H-1 nuclear magnetic resonance spectroscopy, gel permeation chromatography, and infrared and Raman spectroscopy confirm their cyclic structure and, by inference, the cyclic topology of the resulting c-PA. Solid-state thermal analyses via thermogravimetric analysis and differential scanning calorimetry reveal the chemical and physical transformations occurring during the retro-Diels-Alder elimination step and concurrent isomerization. Freestanding films are attainable via the soluble precursors, and when doped with I-2, the films are semiconducting.
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