Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 38, Pages 11191-11195Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504822
Keywords
boron; conjugation; cross-coupling; heterocycles; polymers
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Funding
- National Science Foundation [CHE-1362460, CHE-1361618]
- Camille Dreyfus Teacher-Scholar Awards Program
- Direct For Mathematical & Physical Scien [1362460] Funding Source: National Science Foundation
- Division Of Chemistry [1362460] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1361618] Funding Source: National Science Foundation
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The regioregular synthesis of the first azaborine oligomers and a corresponding conjugated polymer was accomplished by Suzuki-Miyaura coupling methods. An almost perfectly coplanar syn arrangement of the heterocycles was deduced from an X-ray crystal structure of the dimer, which also suggested that N-H center dot center dot center dot pi interactions play an important role. Computational studies further supported these experimental observations and indicated that the electronic structure of the longer azaborine oligomers and polymer resembles that of poly(cyclohexadiene) more than poly(p-phenylene). A comparison of the absorption and emission properties of the polymer with those of the oligomers revealed dramatic bathochromic shifts upon chain elongation, thus suggesting highly effective extension of conjugation.
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