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π-Electron Conjugation in Two Dimensions.

Organic oligomers and polymers with extended π-conjugation are the fundamental building blocks of organic electronic devices. Novel routes are being explored to create tailor-made organic materials, and recent progress in organic chemistry and surface chemistry has led to the synthesis of planar 2D...

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Published in:Journal of the American Chemical Society Vol. 135; no. 44; pp. 16585 - 16595
Main Authors: Gutzler, Rico, Perepichka, Dmitrii F.
Format: Article
Published: American Chemical Society 11/6/2013
Subjects:
Organic chemistry
Organic compounds
Organic electronics
Organic electrochemistry
Bioconjugates
Density functional theory
Oligomers
Polymers
Online Access:View this record in EBSCOhost
Summary:Organic oligomers and polymers with extended π-conjugation are the fundamental building blocks of organic electronic devices. Novel routes are being explored to create tailor-made organic materials, and recent progress in organic chemistry and surface chemistry has led to the synthesis of planar 2D polymers. Here we show how extending π-conjugation in the second dimension leads to novel materials with HOMO–LUMO gaps smaller than in 1D polymers built from the same parent molecular repeat unit. Density functional theory calculations on experimentally realized 2D polymers grant insight into HOMO–LUMO gap contraction with increasing oligomer size and show fundamental differences between 1D and 2D “band gap engineering”. We discuss how the effects of cross-conjugation and dihedral twists affect the electronic gaps.