Synthesis and Characterization of Electron-Deficient Asymmetrically Substituted Diarylindenotetracenes

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

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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
Issue number4
StatePublished - Feb 16 2018


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