Synthesis of 1,3-diphenyl-6-alkyl/aryl-substituted fulvene chromophores: observation of π-π interactions in a 6-pyrene-substituted 1,3-diphenylfulvene.

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.