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:
Online Access:View this record in EBSCOhost
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      dt: 11/6/2013
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      pub: American Chemical Society
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        92594190
        10.1021/ja408355p
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        atl: π-Electron Conjugation in Two Dimensions.
      aug:
        au:
          Gutzler, Rico
          Perepichka, Dmitrii F.
        affil:
          Max Planck Institute for Solid State Research, Heisenbergstrasse 1, 70569 Stuttgart, Germany
          Department of Chemistry and Centre for Self-Assembled Chemical Structures, McGill University, Montreal, Quebec H3A 0B8, Canada
      su:
        Organic chemistry
        Organic compounds
        Organic electronics
        Organic electrochemistry
        Bioconjugates
        Density functional theory
        Oligomers
        Polymers
      sug:
        subj:
          Organic chemistry
          Organic compounds
          Organic electronics
          Organic electrochemistry
          Bioconjugates
          Density functional theory
          Oligomers
          Polymers
      ab: 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.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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