Journal
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Volume -, Issue 5, Pages 768-773Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejic.201501279
Keywords
Fluorescence; Phosphaalkenes; Benzazaphospholes; Organophosphorus compounds; Heterocycles
Categories
Funding
- National Science Foundation [NSF-CHE 1150721]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1150721, 1464855] Funding Source: National Science Foundation
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A carbazole-based azaphosphole (compound 3) has been prepared by acid-catalyzed dehydrocyclization of 1-phosphino-9H-carbazole (2) with benzoyl chloride. Unlike other benzazaphospholes having sigma(2),lambda(3)-multiply bonded phosphorus atoms, compound 3 displays significant fluorescence in solution, as does primary phosphine 2. Compound 3, as well as the materials on route to its synthesis, were characterized by multinuclear NMR, UV/Vis, and fluorescence spectroscopy. The optical data of 2 and 3 are consistent with results of DFT and TDDFT [6-311G+(d,p) CAMB3LYP] calculations. The computed structure of compound 3' (R = Ph) is also consistent with the experimental X-ray structural determination, which reveals a planar heterocyclic system and slight rotation of the p-tolyl group out of plane with respect to the heterocyclic core.
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