Advances in Synthetic Metals by P. Bernier, G. Bidan, S. Lefrant

By P. Bernier, G. Bidan, S. Lefrant

This edited paintings includes 8 vast, review-type contributions via best scientists within the box of man-made metals. The authors have been invited via the organisers of the overseas convention on technology and expertise of artificial Metals '98 (ICSM'98) to study the growth of study long ago twenty years in a unifying and pedagogical demeanour. the current paintings highlights the state of the art of the sphere and assesses the customers for destiny study.

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When treating haloaromatic compounds with magnesium metal in the presence of transition metals as catalysts [80] the yellow PPP-material formed is superior to the black product obtained by oxidative coupling, but also possesses relatively low molecular weight (scheme 7 (3)). To achieve higher molecular weight it was unavoidable to improve the solubility by introducing functionalized starting compounds that carry additional solubilizing alkyl chains [81]. Clearly, monoalkyl dihalobenzenes cause a regioselectivity problem, which can be avoided by using the corresponding 2,5-dialkyl compounds 6.

Regiochemical control to obtain the desired head-to-tail products is still missing for oligothiophenes exceeding three repeat units. This is due to the problems in obtaining isomer-free building blocks with a 2,4-substitution pattern. However, some differently functionalized, regioregular terthiophenes have been synthesized utilizing low-valent transition-metal catalysts [154]. 6. Polypyrrole The main interest in polypyrrole (PPy) 21 stems from the excellent long-term stability of its conductive state as compared, for example, with that of polythiophene, and from the possibility of tailoring its properties by synthesis [155].

The first approach towards Sugimoto and Yoshino FeCI3 95 94 Wudl 1. Mg, Et20, reflux 2. Ni(dppp)CI2, anisol, 100~ 96 20 Yamamoto Ni(COD)2, P(Ph)3 Br-~~~Br DMF, 60~ - 80~ 97 Scheme 22 Chemical approach towards unsubstituted PT. 20 Years of "Synthetic Metals" R a) 45 Dehalogenation Polymerization X ' ~ X x= Br, I 98 R b) C l H g ~ H g C l N i] cat. Demercuration polymerization Cu, PdCI2 pyridine, A 99 r R Sugimoto FeCI3 100 R Hotta d) FeCI3or AICI3 Y = CI, Br 101 Scheme 23 Synthesisof poly-(3-alkylthiophene)s (PAT).

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