Synthesis and Characterization of Electron-Deficient Asymmetrically Substituted Diarylindenotetracenes

Lafe J. Purvis, Xingxian Gu, Soumen Ghosh, Zhuoran Zhang, Chris Cramer, Christopher J Douglas

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Electron-deficient asymmetrically substituted diarylindenotetracenes were prepared via a series of Friedel-Crafts acylations, aryl-aryl cross-couplings, and an intramolecular oxidative cyclization to form the indene ring. Single-crystal X-ray experiments showed good π-π overlap with π-π distances ranging from 3.26 to 3.76 Å. Both thermogravimetric analysis and differential scanning calorimetry indicated that asymmetrically substituted indenotetracenes (ASIs) are stable at elevated temperatures. From cyclic voltammetry experiments, HOMO/LUMO energy levels of ASI derivatives were determined to be near -5.4/-4.0 eV. UV/visible absorption spectra showed strong absorption of light between 400 and 650 nm with molar attenuation coefficients from 104 to 105 M-1 cm-1. ASIs were also found to have very low fluorescence quantum yields, less than 4%. Using the solid-state packing determined from the single-crystal X-ray experiments, computational modeling indicated that ASI molecules should favor electron transport.

Original languageEnglish (US)
Pages (from-to)1828-1841
Number of pages14
JournalJournal of Organic Chemistry
Volume83
Issue number4
DOIs
StatePublished - Feb 16 2018

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Electrons
Single crystals
X rays
Acylation
Experiments
Cyclization
Quantum yield
Electron energy levels
Cyclic voltammetry
Thermogravimetric analysis
Absorption spectra
Differential scanning calorimetry
Fluorescence
Derivatives
Molecules
Temperature
Electron Transport
indene

PubMed: MeSH publication types

  • Journal Article
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

Cite this

Synthesis and Characterization of Electron-Deficient Asymmetrically Substituted Diarylindenotetracenes. / Purvis, Lafe J.; Gu, Xingxian; Ghosh, Soumen; Zhang, Zhuoran; Cramer, Chris; Douglas, Christopher J.

In: Journal of Organic Chemistry, Vol. 83, No. 4, 16.02.2018, p. 1828-1841.

Research output: Contribution to journalArticle

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AU - Purvis, Lafe J.

AU - Gu, Xingxian

AU - Ghosh, Soumen

AU - Zhang, Zhuoran

AU - Cramer, Chris

AU - Douglas, Christopher J

PY - 2018/2/16

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N2 - Electron-deficient asymmetrically substituted diarylindenotetracenes were prepared via a series of Friedel-Crafts acylations, aryl-aryl cross-couplings, and an intramolecular oxidative cyclization to form the indene ring. Single-crystal X-ray experiments showed good π-π overlap with π-π distances ranging from 3.26 to 3.76 Å. Both thermogravimetric analysis and differential scanning calorimetry indicated that asymmetrically substituted indenotetracenes (ASIs) are stable at elevated temperatures. From cyclic voltammetry experiments, HOMO/LUMO energy levels of ASI derivatives were determined to be near -5.4/-4.0 eV. UV/visible absorption spectra showed strong absorption of light between 400 and 650 nm with molar attenuation coefficients from 104 to 105 M-1 cm-1. ASIs were also found to have very low fluorescence quantum yields, less than 4%. Using the solid-state packing determined from the single-crystal X-ray experiments, computational modeling indicated that ASI molecules should favor electron transport.

AB - Electron-deficient asymmetrically substituted diarylindenotetracenes were prepared via a series of Friedel-Crafts acylations, aryl-aryl cross-couplings, and an intramolecular oxidative cyclization to form the indene ring. Single-crystal X-ray experiments showed good π-π overlap with π-π distances ranging from 3.26 to 3.76 Å. Both thermogravimetric analysis and differential scanning calorimetry indicated that asymmetrically substituted indenotetracenes (ASIs) are stable at elevated temperatures. From cyclic voltammetry experiments, HOMO/LUMO energy levels of ASI derivatives were determined to be near -5.4/-4.0 eV. UV/visible absorption spectra showed strong absorption of light between 400 and 650 nm with molar attenuation coefficients from 104 to 105 M-1 cm-1. ASIs were also found to have very low fluorescence quantum yields, less than 4%. Using the solid-state packing determined from the single-crystal X-ray experiments, computational modeling indicated that ASI molecules should favor electron transport.

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