Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 1, Issue 8, Pages 878-882Publisher
AMER CHEMICAL SOC
DOI: 10.1021/sc4000576
Keywords
Microwave heating; Direct arylation; Polycondensation; Conjugated polymer; Highly pure polymer
Categories
Funding
- Collaborative Research Program of Institute for Chemical Research, Kyoto University
- Industrial Technology Research Grant Program from New Energy and Industrial Technology Development Organization (NEDO) of Japan
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For synthesis of pi-conjugated polymers, polycondensation via direct arylation reactions of C-H bonds in aromatic monomers with dibromo-arylenes has attracted increasing attention as a simple synthetic method in which the preparation of organometallic reagents is unnecessary. To develop direct arylation polycondensation for practical use in the synthesis of optoelectronic polymer materials, microwave-assisted reactions were investigated and optimized in terms of a kind of base, concentration, reaction time, and amount of catalyst. Under the optimized conditions, the microwave-assisted direct arylation of 3,4-ethyleneidioxythiophene with dibromofluorene for 30 min with catalyst (1 mol %) gave the corresponding polymer with an extremely high molecular weight up to 147 000. The high molecular weight of the polymer enables formation of a large and flexible self-standing film, leading to an advantage in fabricating organic thin-film devices. The elemental analysis and MALDI-TOF-MS reveal that the polymer has high purity and no bromo- and metallo-terminals. Because only microwave-assisted direct arylation provided these features in the polymer, the present method is superior to conventional methods. Therefore, microwave-assisted polycondensation via direct arylation methodology lends itself well to practical application using inherent product from economical and environmental points of view for the synthesis of pure optoelectronic materials.
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