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

Peloquin, Andrew
J.; Stone, Rebecca L.; Avila, Sarah E.; Rudico, Erlyn R.; Horn, Christopher B.; Gardner, Kim A.; Ball, David W.; E. B. Johnson, Jane; Iacono, Scott T.; Balaich, Gary J.

doi:10.1021/jo301101x.s001

jo301101x_si_001.pdf (1.29 MB)

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

journal contribution

posted on 2012-07-20, 00:00 authored by Andrew J. Peloquin, Rebecca L. Stone, Sarah E. Avila, Erlyn R. Rudico, Christopher B. Horn, Kim A. Gardner, David W. Ball, Jane E. B. Johnson, Scott T. Iacono, Gary J. Balaich

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.