Premium
(Trialkoxysilyl)tetrathiafulvalenes: Precursors of Organized Organic‐Inorganic Hybrid Materials by Sol‐Gel Chemistry
Author(s) -
Bellec Nathalie,
Lerouge Frédéric,
Pichon Benoît,
Cerveau Geneviève,
Corriu Robert J. P.,
Lorcy Dominique
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400485
Subject(s) - chemistry , condensation polymer , alkylation , electrochemistry , monomer , hybrid material , polymer chemistry , tetrathiafulvalene , isocyanate , organic chemistry , hydrolysis , covalent bond , nucleophile , sol gel , polymer , catalysis , chemical engineering , molecule , electrode , engineering , polyurethane
The synthesis, characterization and electrochemical behaviour of novel monomers for use in sol‐gel processes are described. These new compounds include a rigid tetrathiafulvalene (TTF) core substituted by one or two spacers, to which a triethoxysilyl group is covalently bonded. The synthesis is based on the preparation of various cyanoethyl‐protected TTF thiolates, deprotection and alkylation of thiolate with 2‐bromoethanol, and subsequent condensation of the alcohol function with 3‐(triethoxysilyl)propyl isocyanate. The donor ability of the title compounds has been investigated by electrochemical studies. The hydrolytic polycondensation of these new precursors was performed in THF solution in the presence of nucleophile (tetrabutylammonium fluoride, TBAF) or acid (HCl) catalysts. The resulting hybrid solids are highly polycondensed and present organization at both the nanometric (X‐ray diffraction) and micrometric (birefringence) scales. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)