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Synthesis and Electron Accepting Properties of Two Di(benz[f]indenone)-Fused Tetraazaanthracene Isomers

Abstract : We designed and synthesized a novel di(benz[f]indenone)-fused tetraazaanthracene derivative and isolated its two isomers, 1a and 1s, having anti and syn configurations, respectively. Their structure and that of the condensation reaction intermediates, anti-2a and syn-2s, were fully characterized using one- and two-dimensional nuclear magnetic resonance spectroscopy and single-crystal X-ray diffraction. The optical and electronic properties of 1a and 1s were investigated using ultraviolet-visible absorption and fluorescence spectroscopies, cyclic voltammetry, and time-dependent density functional theory calculations. The presence of the carbonyl and ethynyltris(isopropyl)silane groups endows the di(benzoindenone)-fused azaacene derivatives with a strong electron accepting character. With an electron affinity of approximately -3.7 eV, the two isomers represent attractive electron-deficient molecular systems for the generation of n-channel semiconducting materials. Organic field effect transistors of 1a and 1s showed electron transport, and organic solar cells gave a proof of concept of the potential of the two compounds as electron acceptor materials when they are paired with an electron donor polymer.
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https://hal.archives-ouvertes.fr/hal-03594115
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Submitted on : Monday, March 14, 2022 - 9:06:42 AM
Last modification on : Wednesday, April 27, 2022 - 4:59:54 AM
Long-term archiving on: : Wednesday, June 15, 2022 - 6:07:49 PM

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Bruno Salgues, Rudraditya Sarkar, Muhammad Fajri, Yatzil Avalos-Quiroz, Anne-Doriane Manick, et al.. Synthesis and Electron Accepting Properties of Two Di(benz[f]indenone)-Fused Tetraazaanthracene Isomers. Journal of Organic Chemistry, American Chemical Society, 2022, 87, pp.3276 - 3285. ⟨10.1021/acs.joc.1c02942⟩. ⟨hal-03594115⟩

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