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

Josh Vura-Weis; Mark A. Ratner; Michael R. Wasielewski

doi:10.1021/ja907761e

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

Josh Vura-Weis, Mark A. Ratner, Michael R. Wasielewski

Northwestern University

Research output: Contribution to journal › Article › peer-review

94 Citations (Scopus)

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 language	English
Pages (from-to)	1738-1739
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	132
Issue number	6
DOIs	https://doi.org/10.1021/ja907761e
Publication status	Published - Mar 1 2010

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja907761e

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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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