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1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss.

ABSTRACT: The synthesis and properties of 1,2,3,4-tetrahydro-1,4,5,8-tetraazaanthracene (THTAA) - a heterocycle involving both >N-H donating and =N- accepting moieties - have been reinvestigated. Unlike previously reported, THTAA is a thermally stable compound that can be re-sublimed at 300-310 °C without decomposition. Controlled introduction of substituents at the nitrogen atoms of THTAA led to variation of its electron donor/acceptor capability that allowed fine-tuning the absorption properties. The propensity of these compounds and a number of its derivatives to form infinite chains involving >N-H···N= and >N-H···Hal^-···N⁺ atoms is demonstrated by X-ray structure analysis. The DFT level optimized and experimental geometry of THTAA and its derivatives show considerable loss of aromaticity within the quinoxaline moiety.

SUBMITTER: Heynderickx A

PROVIDER: S-EPMC6720741 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss.

Heynderickx Arnault A Nénon Sébastien S Siri Olivier O Lokshin Vladimir V Khodorkovsky Vladimir V

Beilstein journal of organic chemistry 20190828

The synthesis and properties of 1,2,3,4-tetrahydro-1,4,5,8-tetraazaanthracene (THTAA) - a heterocycle involving both >N-H donating and =N- accepting moieties - have been reinvestigated. Unlike previously reported, THTAA is a thermally stable compound that can be re-sublimed at 300-310 °C without decomposition. Controlled introduction of substituents at the nitrogen atoms of THTAA led to variation of its electron donor/acceptor capability that allowed fine-tuning the absorption properties. The pr ...[more]

PMID: 31501674

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