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

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

This edited paintings comprises 8 wide, review-type contributions by way of top scientists within the box of artificial metals. The authors have been invited by means of the organisers of the foreign convention on technological know-how and expertise of man-made Metals '98 (ICSM'98) to check the growth of analysis long ago 20 years in a unifying and pedagogical demeanour. the current paintings highlights the cutting-edge of the sphere and assesses the customers for destiny study.

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The mechanism of the electrochemical polymerization of thiophene is not yet fully understood, but is believed to proceed by the recombination of two radical cations 92 formed by the oxidation of the monomer in the electrochemical step (scheme 21). Aromatization of the intermediate bithiophene 93 constitutes the driving force of the subsequent chemical step. The electropolymerization then proceeds by succesive oxidation and rearomatization steps until the polymer becomes insoluble in the electrolytic medium and precipitates in its oxidized form on the surface of the electrode.

An interesting variant is the transition-metal-induced coupling of dihaloaryls 75 and 78 with bis-tributyl-stannylethylene 76 to yield o-PPV 77 and m-PPV 79 by the Stille reaction (scheme 15) [l17f]. The ortho- and meta- subunits present in these structures provide, on the one hand, improved solubility. On the other, these units interrupt the w-conjugation and induce a localization of the charges on the stilbene building blocks. The Wurtz-type polymerization reaction represents another type of polycondensation reaction towards PPV [l17d], where a chromium bisacetate mediated reductive coupling of bis(geminal)xylenetetrachloride 80 yields, due to the arylsubstituents at the stilbene units, soluble PPVs (scheme 16).

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). poly(3-alkyl)thiophene (PAT) used the nickel-mediated Kumada reaction of 2,5-diiodo-3-alkylthiophene 98 (scheme 23a, X =I) [137]. Advantages of this synthetic path are the exclusively formed 2,5-linkages, as proved by 1H NMR, and the large quantities available; the disadvantage is the regioirregular connection of the thiophene units (see below).

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