Geometry and electronic coupling in perylenediimide stacks: Mapping structure - charge transport relationships

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Abstract

(Chemical Equation Presented) The binding energy and electronic coupling of perylenediimide (PDI) Π-stacked dimers were calculated using M06-2X/6-31++G** as a function of stacking geometry. Due to shallow minima in the potential energy surface, electronic coupling can vary by over an order of magnitude among energetically accessible geometries. The coupling was then determined for 20 PDI derivatives with various substitutions at the imide region, and several were identified as the most promising candidates for organic thin film transistors (OTFTs). This strategy of side-by-side comparison of binding energy and electronic coupling may prove useful for other Π-stacked OTFTs such as pentacene and poly(thiophene) derivatives.

Original languageEnglish
Pages (from-to)1738-1739
Number of pages2
JournalJournal of the American Chemical Society
Volume132
Issue number6
DOIs
Publication statusPublished - 2010

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Thin film transistors
Binding energy
Charge transfer
Imides
Derivatives
Thiophenes
Potential energy surfaces
Geometry
Thiophene
Dimers
Substitution reactions
perylenediimide
pentacene

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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T1 - Geometry and electronic coupling in perylenediimide stacks

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AU - Vura-Weis, Josh

AU - Ratner, Mark A

AU - Wasielewski, Michael R

PY - 2010

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AB - (Chemical Equation Presented) The binding energy and electronic coupling of perylenediimide (PDI) Π-stacked dimers were calculated using M06-2X/6-31++G** as a function of stacking geometry. Due to shallow minima in the potential energy surface, electronic coupling can vary by over an order of magnitude among energetically accessible geometries. The coupling was then determined for 20 PDI derivatives with various substitutions at the imide region, and several were identified as the most promising candidates for organic thin film transistors (OTFTs). This strategy of side-by-side comparison of binding energy and electronic coupling may prove useful for other Π-stacked OTFTs such as pentacene and poly(thiophene) derivatives.

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