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Titolo:
Highly conjugated poly(thiophene)s - Synthesis of regioregular 3-alkylthiophene polymers and 3-alkylthiophene/thiophene copolymers
Autore:
Lere-Porte, JP; Moreau, JJE; Torreilles, C;
Indirizzi:
Ecole Natl Super Chim, Lab Chim Organomet, UMR CNRS 5076, F-34296 Montpellier 5, France Ecole Natl Super Chim Montpellier France 5 F-34296 Montpellier 5, France
Titolo Testata:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 7, , anno: 2001,
pagine: 1249 - 1258
SICI:
1434-193X(200104):7<1249:HCP-SO>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
ELECTROCHEMICALLY-PREPARED POLY(3-DODECYLTHIOPHENE); STRUCTURE-PROPERTY RELATIONSHIPS; CROSS-COUPLING REACTIONS; OPTICAL-PROPERTIES; CONDUCTING POLYTHIOPHENES; POLY(3-ALKYLTHIOPHENES); POLYMERIZATION; CHEMISTRY; THIOPHENE; DERIVATIVES;
Keywords:
conducting materials; polythiophene; palladium; organometallic coupling;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
58
Recensione:
Indirizzi per estratti:
Indirizzo: Moreau, JJE Ecole Natl Super Chim, Lab Chim Organomet, UMR CNRS 5076, 8 Rue Ecole Normale, F-34296 Montpellier 5, France Ecole Natl Super Chim 8 Rue Ecole Normale Montpellier France 5
Citazione:
J.P. Lere-Porte et al., "Highly conjugated poly(thiophene)s - Synthesis of regioregular 3-alkylthiophene polymers and 3-alkylthiophene/thiophene copolymers", EUR J ORG C, (7), 2001, pp. 1249-1258

Abstract

Tributyltin derivatives of 2-bromo-3-octylthiophene and 5-bromo-4-octyl-2,2'-bi(thiophene) have been selectively prepared. Condensation reactions in the presence of Pd-2(dba)(3)(CHCl3)/4 PPh3 led to high yields (ca. 90%) of regioregular poly(3-octylthiophene) (M-w= 21.4 x 10(4), M-w/ M-n = 1.48) and poly[4-octylbi(thiophene)] (M-w = 3.8 x 10(4), M-w/M-n = 1.1). The regioregularity of the head-to-tail (HT) coupling has been determined by H-1 NMR,which showed HT > 95% for poly(3 -octylthiophene) and HT > 90% for the newpoly[4-octylbi(thiophene)]. The conjugation properties of these materials have been characterized by FT-IR and UV/ Vis spectroscopy. Compared to the corresponding random polymers, the absorption maxima of the new regular polymers are shifted to higher wavelengths (lambda (max) = 448 and 466nm, respectively). The mean conjugation length increases with increasing regioregularity of the coupling and with fewer substituents along the conjugated chain. The electroactive properties of the materials have also been studied. The new poly[4-octylbi(thiophene)] shows an oxidation peak at a low potential, and, compared to poly(3-octyl-thiophene), a reduction peak is also observed at a lower potential indicating a higher electron affinity. Both polymers exhibit reversible blue-red electrochromic behavior associated with the reversible redox properties.

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Documento generato il 25/09/20 alle ore 05:24:45