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

Shinji Ando; Antonio Facchetti; Tobin J. Marks

doi:10.1021/ol1020338

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

Shinji Ando, Antonio Facchetti^*, Tobin J. Marks

^*Corresponding author for this work

Chemistry

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

7 Scopus citations

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 language	English (US)
Pages (from-to)	4852-4855
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	21
DOIs	https://doi.org/10.1021/ol1020338
State	Published - Nov 5 2010

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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.",

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year = "2010",

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doi = "10.1021/ol1020338",

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journal = "Organic Letters",

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TY - JOUR

T1 - Synthesis and characterization of solution-processable core-cyanated perylene-3,4;9,10-bis(dicarboximide) derivatives

AU - Ando, Shinji

AU - Facchetti, Antonio

AU - Marks, Tobin J.

PY - 2010/11/5

Y1 - 2010/11/5

N2 - 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.

AB - 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.

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JO - Organic Letters

JF - Organic Letters

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

Abstract

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