Alkyl- and aryl-substituted benzo[ghi]perylenetriimides: Synthesis, characterization and comparison of electrochemical and spectroscopic properties

Lakshmi C.Kasi Viswanath, Jeremy Bernhardt, Krishna Kumar Gnanasekaran, Colton Want, Joshua Frank, Jantzen Faulkner, Sadagopan Krishnan

Research output: Contribution to journalArticle

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Abstract

Benzo[ghi]peryleneimides constitute a unique class of fluorescent perylene dyes which possesses great synthetic diversity due to the presence of a large number of reactive active sites (availability of third imide region). Taking advantage of this additional active site we synthesized a new series of benzo[ghi]perylenetriimides comprised of alkyl- and aryl-substituents in the third imide region. The core extension of perylene diimides was performed using a Diels-Alder reaction to afford diimido anhydride (3) which provided access to the various triimides with yields ranging from 58% to 69%. The combined spectroscopic and electrochemical studies revealed strong electron accepting properties of the triimides. Potential application of the synthesized triimides for various optoelectronic devices and as non-fullerene electron acceptors in photovoltaics is evident from this study.

Original languageEnglish
Pages (from-to)453-458
Number of pages6
JournalDyes and Pigments
Volume134
DOIs
StatePublished - 1 Nov 2016
Externally publishedYes

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Keywords

  • Benzo[ghi]perylenetriimide
  • Diels-Alder
  • Electron transfer
  • Organic solar cells
  • Perylene diimides

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