Synthesis and optical properties of diaza- and tetraazatetracenes

Chemistry : a European Journal
Benjamin D LindnerUwe H F Bunz

Abstract

A series of functionalized diaza- and tetraazatetracenes was synthesized, either by condensation of an aromatic diamine with an ortho-quinone/diethyloxalate followed by chlorination with POCl(3) to give diazatetracenes or by palladium-catalyzed coupling of a phenylenediamine with various 2,3-dichloroquinoxalines to give tetraazatetracenes (after oxidation with MnO(2)). Representative examples included halogenated and nitrated derivatives. The optical properties of these azatetracenes were discussed with respect to their molecular structures and substitution patterns. The diazatetracenes and tetraazatetracenes formed two different groups that had significantly different electronic structures and properties. Furthermore, 1,2,3,4-tetrafluoro-6,11-bis((triisopropylsilyl)ethynyl)benzo[b]phenazine was synthesized, which is the first reported fluorinated diazatetracene. Single-crystal X-ray analysis of this compound is reported.

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Citations

Nov 13, 2015·The Journal of Organic Chemistry·Florian L GeyerUwe H F Bunz
Mar 31, 2016·Chemistry : a European Journal·Shuaijun YangQian Miao
Nov 20, 2014·The Journal of Organic Chemistry·Philipp BieggerU H F Bunz
Aug 23, 2016·Physical Chemistry Chemical Physics : PCCP·Ramachandran Rakhi, Cherumuttathu H Suresh
Feb 20, 2013·Angewandte Chemie·Uwe H F BunzManuel Schaffroth
Aug 19, 2014·Chemical Communications : Chem Comm·Kamil KotwicaAdam Pron
Jan 11, 2014·Chemical Communications : Chem Comm·Sandeep MoreAurelio Mateo-Alonso
Dec 11, 2013·Chemistry : a European Journal·Sunil ChoudharyAurelio Mateo-Alonso
Sep 12, 2012·Angewandte Chemie·Kiyohiko GotoHiroshi Shinokubo
Jul 2, 2021·Chemistry : a European Journal·Maximilian ElterUwe H F Bunz
Feb 12, 2013·The Journal of Organic Chemistry·Manuel SchaffrothU H F Bunz
May 15, 2015·Accounts of Chemical Research·Uwe H F Bunz
Jul 10, 2013·ACS Applied Materials & Interfaces·Gang LiQichun Zhang
May 21, 2015·ACS Applied Materials & Interfaces·Junbo Li, Qichun Zhang
Nov 28, 2013·The Journal of Organic Chemistry·Rajneesh MisraShaikh M Mobin
Sep 28, 2013·The Journal of Organic Chemistry·Jens U EngelhartUwe H F Bunz
May 1, 2013·The Journal of Organic Chemistry·Rajneesh MisraShaikh M Mobin
Jan 17, 2013·Organic Letters·Benjamin D LindnerUwe H F Bunz
Dec 12, 2012·Journal of the American Chemical Society·Gang LiQichun Zhang

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