Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 18, Pages 6578-6587Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja101845m
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Funding
- National Science Foundation [CHE-0906179, CHE-0840504]
- Robert A. Welch Foundation [N-1322]
- Alexander von Humboldt Foundation
- NIU Inaugural Board of Trustees
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0906179] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0840504] Funding Source: National Science Foundation
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A series of C-3-symmetric pi-conjugated compounds containing three to six o-carborane clusters have been synthesized by employing palladium-catalyzed Suzuki coupling reactions and palladium-catalyzed acetylation reactions, followed by silicon tetrachloride mediated trimerization reactions. Carborane-containing extended trimers were found to emit blue light. Incorporation of o-carborane clusters into extended pi-conjugated systems led to 22-70% enhancement of their relative fluorescence quantum yields. Decapitation of o-carborane clusters made these extended trimers water soluble, and their aqueous solutions were also found to be fluorescent, but with a reduced fluorescence intensity. The carborane-appended pi-conjugated compounds are found to be extremely thermally stable, and for some of these compounds only 10% mass loss occurred at temperatures close to 500 degrees C. The DSC thermograms of smaller C-cage-appended trimers indicate the occurrence of solid solid phase transitions.
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