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Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene

By Andrew J. Peloquin (2062696), Rebecca L. Stone (214799), Sarah E. Avila (2062693), Erlyn R. Rudico (2062702), Christopher B. Horn (2062699), Kim A. Gardner (2062708), David W. Ball (2046082), Jane E. B. Johnson (2062705), Scott T. Iacono (1536721) and Gary J. Balaich (1723240)


The synthesis, structural, and electronic properties of nine 1,3-diphenyl-6-alkyl/aryl substituted pentafulvenes were studied. Pyrene ring π–π interactions were revealed from analysis of the experimental crystal packing of 1,3-diphenyl-6-(1-pyrene)­fulvene and supporting DFT calculations. Photophysical properties derived from UV–vis and fluorescence emission measurements demonstrated tunable and low HOMO–LUMO band gaps for the series. The presented results point to a model synthetic approach for incorporation of extended π systems and donor-π-acceptor groups for fulvene-based electronic materials

Topics: Biochemistry, Medicine, Pharmacology, Biotechnology, Ecology, Sociology, Virology, Space Science, Environmental Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, UV, series, Diphenyl, HOMO, tunable, π systems, pentafulvene, fluorescence emission measurements, Chromophore, diphenyl, Pyrene, results point, synthesis, model, Interaction, DFT calculations, material, gap, incorporation, donor, DiphenylfulveneThe, interaction, approach, Fulvene, analysis, crystal, Photophysical properties, Synthesi
Year: 2012
DOI identifier: 10.1021/jo301101x.s001
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