124537-32-2Relevant articles and documents
Domino Cross-Scholl Reaction of Tetracene with Molecular Benzene: Synthesis, Structure, and Mechanism
Harada, Ai,Kishimoto, Yusho,Mishima, Daisuke,Muraoka, Masahiro,Murata, Michihisa,Nakanishi, Haruka,Togo, Masahiro,Tsuboi, Yui,Yamada, Yuto,Yamanaka, Yohei
supporting information, p. 7921 - 7926 (2021/10/12)
A domino-type multiple C-H functionalization of tetracene with molecular benzene is reported. Under the typical conditions of the Scholl reaction, a domino reaction occurs between tetracene and six molecules of benzene in one pot to furnish an aromatic compound with a curved π-system. This reaction sequence involves oxidative cross-dehydrogenative coupling/annulation and Friedel-Crafts-type reactions. Eight C-C bonds are formed via this intermolecular domino reaction without mediation by a metal or the assistance of a specific substituent.
Synthesis and Characterization of Electron-Deficient Asymmetrically Substituted Diarylindenotetracenes
Purvis, Lafe J.,Gu, Xingxian,Ghosh, Soumen,Zhang, Zhuoran,Cramer, Christopher J.,Douglas, Christopher J.
, p. 1828 - 1841 (2018/02/23)
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 ?. 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.
Diarylindenotetracenes via a selective cross-coupling/C-H functionalization: Electron donors for organic photovoltaic cells
Gu, Xingxian,Luhman, Wade A.,Yagodkin, Elisey,Holmes, Russell J.,Douglas, Christopher J.
supporting information; experimental part, p. 1390 - 1393 (2012/05/04)
A direct synthesis of new donor materials for organic photovoltaic cells is reported. Diaryindenotetracenes were synthesized utilizing a Kumada-Tamao-Corriu cross-coupling of peri-substituted tetrachlorotetracene with spontaneous indene annulation via C-H