11,11,12,12-Tetracyano-2,6-anthraquinodimethane (TANT) as a novel extensive electron acceptor

Abstract

The title compound is prepared as a higher homologue in an extensively conjugated series of TCNQ (7,7,8,8tetracyanoquinodimethane) and TNAP (9,9,10,1O-tetracyano-2,6-naphthoquinodimethane); its complexes with TTT (tetrathiatetracene) and HMTTeF (hexamethylenetetratellurafulvalene) are electrically highly conductive.

Guanidine and 2-Aminoimidazoline Aromatic Derivatives as α2-Adrenoceptor Antagonists. 2. Exploring Alkyl Linkers for New Antidepressants

“…Standard Boc deprotection of the intermediates with an excess of trifluoroacetic acid in dichloromethane and further treatment with Amberlyte resin in aqueous solution led to the hydrochloride salts of the target molecules in good overall yields (Table ). All the starting amines are commercially available either from Aldrich or Fluka except for the 9,10-dihydroanthracene-2,6-diamine, which was synthesized according to the procedure reported in the literature …”

Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

“…There are two key issues concerning the application of this precursor: (1) breaking the symmetry of the molecule which involves retaining one amine and converting the other amine to a different functional group (e.g., dialkylating one amine and converting the other to a bromide) and (2) reduction of the 9,10-anthraquinone system to anthracene. The second issue had already been dealt with in a variety of other substituted anthraquinones using either sodium borohydride 13 or zinc in ammonia . Using either of these procedures, we successfully reduced 2,6-diamino-9,10-anthraquinone to 2,6-diaminoanthracene ( 2 ).…”

Pushing Extended p-Quinodimethanes to the Limit: Stable Tetracyano-oligo(N-annulated perylene)quinodimethanes with Tunable Ground States

“…Among them, a series of quinoidal oligothiophenes up to hexamer displayed interesting chain-length dependence of their ground-state electronic structures, with the pentamer and hexamer showing significant singlet biradical character . Incorporation of a p -QDM moiety and its analogues such as 2,6-naphthoquinodimthane and 2,6-anthraquinodimethane into a fused π-conjugated framework has proved to be an efficient way to generate polycyclic hydrocarbons with potential open-shell biradical ground states, and typical examples include indenofluorenes, bis(phenalenyls), and zethrenes . These polycyclic hydrocarbons exhibit unique optical, electronic, and magnetic properties and have promising applications in nonlinear optics, organic electronics, organic spintronics, and energy storage devices …”