Toward an n-type molecular wire: Electron hopping within linearly linked perylenediimide oligomers

Thea M. Wilson; Michael J. Tauber; Michael R. Wasielewski

doi:10.1021/ja902258g

Toward an n-type molecular wire: Electron hopping within linearly linked perylenediimide oligomers

Thea M. Wilson, Michael J. Tauber, Michael R. Wasielewski

Northwestern University

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

78 Citations (Scopus)

Abstract

A series of linearly linked perylenediimide (PDI) dimers and trimers were synthesized in which the PDI π systems are nearly orthogonal. These oligomers and several model compounds were singly reduced, and intramolecular electron hopping between the PDI molecules was probed by electron paramagnetic resonance (EPR) and electron nuclear double resonance (ENDOR) spectroscopy. When the functional groups attached to the ends of the oligomers were chosen to make each PDI molecule electronically equivalent, the single electron hops between the PDI molecules with rates that significantly exceed 10⁷ s ^-1. Rapid electron hopping between pairs of PDI molecules having orthogonal π systems is unexpected and may expand the possible design motifs for organic electronic materials based on PDI.

Original language	English
Pages (from-to)	8952-8957
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	131
Issue number	25
DOIs	https://doi.org/10.1021/ja902258g
Publication status	Published - Jul 1 2009

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja902258g

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AB - A series of linearly linked perylenediimide (PDI) dimers and trimers were synthesized in which the PDI π systems are nearly orthogonal. These oligomers and several model compounds were singly reduced, and intramolecular electron hopping between the PDI molecules was probed by electron paramagnetic resonance (EPR) and electron nuclear double resonance (ENDOR) spectroscopy. When the functional groups attached to the ends of the oligomers were chosen to make each PDI molecule electronically equivalent, the single electron hops between the PDI molecules with rates that significantly exceed 107 s -1. Rapid electron hopping between pairs of PDI molecules having orthogonal π systems is unexpected and may expand the possible design motifs for organic electronic materials based on PDI.

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