Synthesis and characterization of solution-processable core-cyanated perylene-3,4;9,10-bis(dicarboximide) derivatives

Shinji Ando, Antonio Facchetti, Tobin J Marks

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Core-cyanated perylene-3,4;9,10-bis(carboxyimide) derivatives N-functionalized with tethered anthracenes (PDI3A-CN2, PDI4A-CN 2) and the corresponding solution-processable cycloadduct precursors (PDI3A-CA-CN2, PDI4A-CA-CN2) were synthesized and their optical, electrochemical, and thermal properties characterized. These derivatives exhibit HOMO-LUMO energy gaps of ∼2.1-2.3 eV and first reduction potentials between -50 and -150 mV versus SCE. The PDI3A-CN2 and PDI4A-CN2 cycloadducts are soluble in common organic solvents (>50 mg/mL), and the corresponding spin-coated films are converted to PDI3A-CN 2 and PDI4A-CN2 films upon thermal annealing.

Original languageEnglish
Pages (from-to)4852-4855
Number of pages4
JournalOrganic Letters
Volume12
Issue number21
DOIs
Publication statusPublished - Nov 5 2010

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Perylene
Anthracenes
Hot Temperature
Derivatives
synthesis
anthracene
Electrochemical properties
Organic solvents
Energy gap
Thermodynamic properties
Optical properties
thermodynamic properties
Annealing
optical properties
annealing

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis and characterization of solution-processable core-cyanated perylene-3,4;9,10-bis(dicarboximide) derivatives. / Ando, Shinji; Facchetti, Antonio; Marks, Tobin J.

In: Organic Letters, Vol. 12, No. 21, 05.11.2010, p. 4852-4855.

Research output: Contribution to journalArticle

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