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

Arnault Heynderickx, Sébastien Nénon, Olivier Siri, Vladimir Lokshin, Vladimir Khodorkovsky

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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.

Original languageEnglish
Pages (from-to)2059-2068
Number of pages10
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
StatePublished - 28 Aug 2019
Externally publishedYes

Keywords

  • Aromaticity
  • Density functional calculations
  • Heterocycles
  • Hydrogen bonds
  • X-ray structures

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