Publication 663

Eur. J., 16, 8390 -8399, 2010. DOI: 10.1002/chem.201000427
Electroactive Benzothiazole Hydrazones and Their [Mo6O19]2- Derivatives: Promising Building Blocks for Conducting Molecular Materials

Institut Parisien de Chimie Moléculaire, UMR CNRS 7201, UPMC Université Paris 06, Case courrier 42, 4 place Jussieu, 75252 Paris Cedex 05 (France) )
Institut Universitaire de France, 103, bd. Saint-Michel, 75005 Paris (France)
Laboratoire d'Electrochimie Moléculaire, UMR CNRS 7591, Université Paris Diderot Paris 7, Bâtiment Lavoisier, Case 7107, 15 rue Jean-Antoine de Baïf, 75205 Paris Cedex 13 (France)

The electroactive benzothiazole hydrazone AMBTH-H₂, a new member of the 2,2´-azino-bis(N-alkylbenzothiazole) family, was synthesised in a five-step procedure and characterised by using X-ray diffraction along with two intermediates and the N-methylbenzothiazole hydrazone MBTH-H₂. Both AMBTH-H₂ and MBTH-H₂ were coupled to [Mo₆O₁₉]^2- in acetonitrile in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine to give two new diazoalkane-hexamolybdates, which were isolated as tetrabutylammonium salts and characterised by using IR, UV/Vis and NMR spectroscopies, cyclic voltammetry and, for one of them, X-ray diffraction. The packing arrangement molecules in crystals of AMBTH-H₂, the redox features of the AMBTH-hexamolybdate hybrid together with a good electronic communication between the organic system and the molybdenum centres make these compounds very promising blocks for the synthesis of conducting molecular materials.