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Near-IR dyes of a new type featuring multiple tuneable redox states (dia- and paramagnetic, neutral and positively and negatively charged) are synthesized by previously unknown self-condensation of Herz diradical.

Salts of sterically hindered chalcogen-varied Herz cations with various anions were synthesized. 4,6-Di-tert-butylsubstituted 1,2,3-benzothiaselenazolium (2), 2,1,3-benzothiaselenazolium (3), and 1,2,3-benzodiselenazolium (4) were obtained from corresponding 1,2,3-benzodithiazolium (1) or 2bromo-4,6-di-tert-butylaniline (9) and were isolated as salts with [Cl]or/and [SbCl 6 ]anions. Reaction of in situ prepared N,N,Tetris(trimethylsilyl)-2-amino-3,5-di-tert-butyltellurophenole with SeCl 4 , S 2 Cl 2 , and SOCl 2 resulted in elimination of Te and the formation of [4]

New chalcogen-nitrogen π-heterocycles covering 3,1,2,4-benzothiaselenadiazines, 1,3,2,4-benzodithiadiazines and 1,2,4,3,5-benzotrithiadiazepines were synthesized by electrophilic cyclization of compounds Ar–N=S=N–SiMe3 under the action of SeCl2, SeCl4/FeCp2, SCl2 and S2Cl2. Heterocycles obtained were thermolyzed into...

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