Journal
MACROMOLECULAR RAPID COMMUNICATIONS
Volume 34, Issue 14, Pages 1151-1156Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/marc.201300303
Keywords
directing group; 1-(2-pyrimidinyl)pyrrole; polycon-densation; Ru-catalyst; site-selective direct arylation
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Funding
- Institute for Chemical Research, Kyoto University [2013-52]
- New Energy and Industrial Technology Development Organization (NEDO) of Japan
- [25288052]
- [25620094]
- Grants-in-Aid for Scientific Research [25288052] Funding Source: KAKEN
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Polycondensation of 1-(2-pyrimidinyl)pyrrole with 2,7-dibromo-9,9-dioctylfluorene via Ru-catalyzed direct arylation gives the corresponding conjugated polymer with a molecular weight of 19 800 in 86% yield. The introduction of directing group, 2-pyrimidinyl substituent, into the pyrrole monomer induces ortho-metalation and provides the site-selective direct arylation polycondensation at the alpha-position of pyrrole unit without the protection of beta-position. The removal of 2-pyrimidinyl substituent on the pyrrole unit proceeds efficiently and results in the enhancement of coplanarity along the main chain of the polymer.
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