Head-to-tail coupled, regioregular poly

R.S. Loewe, S.M. Khersonsky, and R.D. McCullough, A simple method to prepare head-to-tail coupled, regioregular poly(3-alkylthiophenes) using Grignard metathesis, Adv. Mater., 11 250-253, 1999. 

R.S. Loewe, P.C. Ewbank, J. Liu, L. Zhai, and R.D. McCullough, Regioregular, head-to-tail coupled poly(3-alkylthiophenes) made easy but the GRIM method investigation of the reaction and the origin of regioselectivity, Macromolecules, 34 4324-4333, 2001. 

SCHEME 9.1 The McCullough method for the regioregular synthesis of poly(3-alkylthiophene) (P3AT) with 100% head-to-tail couplings. 

McCullough, R.D. 1998. Regioregular, head-to-tail coupled poly(3-alkylthiophene) and its derivatives. In Handbook of conducting polymers, 2nd ed., eds. T.A. Skotheim, R.L. Elsenbaumer, J. R. Reynolds. NewYork Marcell Dekker, pp. 225-258. 

Regioregular, Head-to-Tail Coupled Poly(3-alkylthiophene) and Its Derivatives... 

IV. REGIOREGULAR, HEAD-TO-TAIL COUPLED POLY(3-ALKYLTHIOPHENES)... 

Guillerez and Bidan [604] recently described a new synthesis of highly regioregular poly(3-octyl-thiophene) based on the Suzuki coupling reaction. The stable polymerizable precursor which bore an iodo and boronic ester derivative in the 2 and 5 positions was obtained in two steps from the 3-octyJ monomer. Polymerization of this in the presence of Pd(II) acetate gave a final CP said to contain up to 97% of head-to-tail couplings. This synthesis is summarized in Fig. 14-4. 

S. Amou, O. Haba, K. Shirato, T. Hayakawa, M. Ueda, K. Takeuchi, and M. Asai, Head-to-tail regioregularity of poly(3-hexylthiophene) in oxidative coupling polymerization with FeCl3, J. Polym. Sci., Part A Polym. Chem., 37 1943-1948, 1999. 

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