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Volume: 46 | Article ID: art00009
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J-aggregate-like Structure and Its Influence on the Electronic Spectrum of 1, 4-diketo-3, 6-bis(4-biphenylyl)pyrrolo[3, 4-c]pyrrole
  DOI :  10.2352/J.ImagingSci.Technol.2002.46.3.art00009  Published OnlineMay 2002
Abstract

The title compound (BP-DPP), known as a red pigment as well as a photoconductor for photoreceptors, is characterized by an extremely large bathochromic shift upon crystallization, as compared with other DPP analogues. The electronic structure of BP-DPP has therefore been investigated from the standpoint of crystal structure and exciton coupling effects. BP-DPP is found to crystallize in the “bricks in a brick wall” fashion, just like J-aggregates in cyanine dyestuffs. On the molecular plane of BP-DPP, there are chains of intermolecular hydrogen bonds between the NH group of one molecule and the O atom of the neighboring one. The hydrogen bond aligns the transition dipoles in a fashion “head-to-tail”, leading to a bathochromic displacement of the absorption maximum. Additionally, there are diagonal pairs of the brick wall structure whose exciton coupling again induces a bathochromic shift. Both the hydrogen bond in the molecular plane and the brick wall structure along the molecular stack are found to displace significantly the absorption band toward longer wavelengths on going from solution to the solid state.

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Jin Mizuguchi, "J-aggregate-like Structure and Its Influence on the Electronic Spectrum of 1, 4-diketo-3, 6-bis(4-biphenylyl)pyrrolo[3, 4-c]pyrrolein Journal of Imaging Science and Technology,  2002,  pp 257 - 261,  https://doi.org/10.2352/J.ImagingSci.Technol.2002.46.3.art00009

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