New convenient synthesis of highly regioregular poly(3-octylthiophene) based on the Suzuki coupling reaction

doi:10.1016/S0379-6779(97)04102-7

Synthetic Metals

Volume 93, Issue 2, 15 March 1998, Pages 123-126

https://doi.org/10.1016/S0379-6779(97)04102-7 Get rights and content

Abstract

In this work, we present a new convenient synthesis leading to a highly regioregular poly(3-octylthiophene) (POT). The stable polymerizable precursor, bearing an iodo and a boronic ester derivative in the 2 and 5 positions, respectively, was obtained in two steps from 3-octylthiophene. Its polymerization, in the presence of palladium(II) acetate, gave a POT containing 96–97% of head—tail to head—tail (HT—HT) couplings.

References (7)

G. Bidan, A. De Nicola, V. Enée and S. Guillerez, to be...
R.D. McCullough et al.
J. Chem. Soc., Chem. Commun.
(1992)
T.-A. Chen et al.
J. Am. Chem. Soc.
(1992)

There are more references available in the full text version of this article.

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Citation Excerpt :
Historically, the impact of regioregularity on the properties of chemically poly(3-alkylthiophenes) has been reported by Elsenbaumer et al. [17]. Further investigations into the characteristics of chemically prepared poly(3-alkylthiophenes) have been carried out by Guillerez [12], Heeger [18] and Dunsch [19]. Interestingly, there has been no mention of solvent-modified electropolymerisation, a deficiency, which would be our intention to compensate for.
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New convenient synthesis of highly regioregular poly(3-octylthiophene) based on the Suzuki coupling reaction

Abstract

J. Chem. Soc., Chem. Commun.

J. Am. Chem. Soc.