Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 21, Pages 5998-6008Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201003382
Keywords
electron transport; electronic structure; fluorescence; self-assembly; silole
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Funding
- Research Grants Council of Hong Kong [603509, 601608, CUHK2/CRF/08, HKUST2/CRF/10]
- Innovation and Technology Commission [ITP/008/09NP, ITS/168/09]
- University Grants Committee of Hong Kong [AoE/P-03/08]
- National Science Foundation of China [20974028]
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2,5-Bis(triphenylsilylethynyl)-3,4-diphenylsiloles with different 1,1-substituents [XYSi(CPh)(2)(C C=C SiPh3)(2)] (Ph = phenyl) were synthesized in high yields by the Sonogashira coupling of 2,5-dibromo-3,4-diphenylsiloles with triphenylsilylacetylene, and two of these were characterized crystallographically. Crystal structures and theoretical calculations showed that the new silole molecules had higher conjugation than 2,5-diarylsiloles. They possessed low HOMO and LUMO energy levels due to the electron-withdrawing effect of the triphenylsilylethynyl groups. Cyclic voltammetry analysis revealed low electron affinities, which same conditions. All of the silole molecules possessed high thermal stability. Although, their solutions were weakly emissive, their nanoparticle suspensions and thin films emitted intense blue-green light upon photoexcitation, demonstrating a novel feature of aggregation-induced emission (AIE). Polarized emissions were observed in the silole crystals. The addition of solvents, which did not dissolve the silole molecules, into silole-containing solutions caused self-assembly of the molecules, which produced macroscopic fibrils with strong light emissions.
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