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Electroactive Benzothiazole Hydrazones and Their [Mo 6 O 19 ] 2− Derivatives: Promising Building Blocks for Conducting Molecular Materials
Author(s) -
Gatard Sylvain,
Blanchard Sébastien,
Schollhorn Bernd,
Gouzerh Pierre,
Proust Anna,
Boubekeur Kamal
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000427
Subject(s) - benzothiazole , materials science , chemistry , nanotechnology , organic chemistry
The electroactive benzothiazole hydrazone AMBTH–H 2 , 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–H 2 . Both AMBTH–H 2 and MBTH–H 2 were coupled to [Mo 6 O 19 ] 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–H 2 , the redox features of the AMBTH–hexamolybdate hybrid together with a good electronic communication between the organic π system and the molybdenum centres make these compounds very promising blocks for the synthesis of conducting molecular materials.