Journal
ORGANIC LETTERS
Volume 10, Issue 17, Pages 3681-3684Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801030u
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Funding
- BGSU [TIE]
- NSF [0731153]
- Div Of Chem, Bioeng, Env, & Transp Sys
- Directorate For Engineering [0731153] Funding Source: National Science Foundation
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1,4-Diarylpentiptycenes (1a-e) were synthesized from 1,4-dichloro- or 1,4-difluoro-2,5-diarylbenzene derivatives by double base-promoted dehydrohalogenation to give corresponding arynes, which in the presence of anthracene undergo cycloaddition providing 1,4-diarylpentiptycenes in moderate overall yields. The resulting 1,4-diarylpentiptycenes show fluorescence modulated by the 1,4-aryl residues. The fluorescence is quenched in the presence of vapors of nitroaromatic compounds suggesting potential application in sensing of explosives.
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