Highly Conductive, Regioregular Alkoxy-Functionalized Polythiophenes:  A New Class of Stable, Low Band Gap Materials

Sheina, Elena E.; Khersonsky, Sonya M.; Jones, E. G.; McCullough, Richard D.

doi:10.1021/cm050083o

Cited by 114 publications

(91 citation statements)

References 44 publications

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“…were also synthesized [45][46][47][48][49][50]. Although no detailed study on the polymerization mechanism was reported, the polymerization may also follow chain-growth mechanism.…”

Section: Pt4-pt9mentioning

confidence: 99%

Kumada chain-growth polycondensation as a universal method for synthesis of well-defined conjugated polymers

et al. 2010

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Kumada chain-growth polycondensation (KCGP) is a novel method for the synthesis of well-defined conjugated polymers. Because the Ni-catalyst can transfer in an intramolecular process to the propagating chain end, the polymerization follows chain-growth mechanism. With this newly developed method, various conjugated polymers, such as polythiophenes, poly(p-phenylene) (PPP), polypyrrole (PPy), and polyfluorene with controlled molecular weights and relatively narrow polydispersities (PDIs), have been prepared. Especially, the polymerizations for poly(3-alkylthiophene)s (P3ATs), PPP, and PPy exhibited quasi-living characteristics, which allows preparing polymer brushes, fully-conjugated block copolymers, and macroinitiators and macro-reactants for the synthesis of rod-coil block copolymers. In the current review, the progress in this new area is summarized.

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“…were also synthesized [45][46][47][48][49][50]. Although no detailed study on the polymerization mechanism was reported, the polymerization may also follow chain-growth mechanism.…”

Section: Pt4-pt9mentioning

confidence: 99%

Kumada chain-growth polycondensation as a universal method for synthesis of well-defined conjugated polymers

et al. 2010

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“…The on/off current ratio were quite low reaching values of 50. This is related to the relatively high off-current (I ds at V g = 0 V) probably originated by the low oxidation potential and highly stable p-type conductive state of alkoxy-substituted conjugated systems [30]. LS POPT OTFTs fabricated on bare t-SiO 2 substrates exhibit much worse field-effect properties.…”

Section: Field-effect Propertiesmentioning

confidence: 99%

Nanostructural depth-profile and field-effect properties of poly(alkoxyphenylene-thienylene) Langmuir–Schäfer thin-films

et al. 2008

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“…[6] As a consequence, the Grignard metathese method (GRIM), starting from the dibromothiophene derivative -as is used for the chain-growth polymerization of HT-P3AT -cannot be employed for the polymerization of HT-P3AOT, since this methods produces both isomers. [10] Also a selective GRIM on 2-iodo-5-bromo-3-alkoxythiophene, even if iPrMgCl·LiCl was employed, was unsuccessful in our hands.…”

Section: Molar Mass Versus [M] 0 /[In]mentioning

confidence: 82%

Ni‐Catalyzed Polymerization of Poly(3‐alkoxythiophene)s

Bergh

Winter

Gerbaux

et al. 2010

Macro Chemistry & Physics

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The Ni-catalyzed polymerization of poly(3-alkoxythiophene)s (P3AOTs) was studied and compared with the controlled chain-growth polymerization of poly(3-alkylthiophene)s (P3ATs). By varying the ratio of the initial monomer concentration to the initiator concentration, no linear dependence of the molar mass was observed, revealing that the polymerization does not proceed via a controlled mechanism. This was also confirmed by analyzing the end-groups of the polymer with MALDI-TOF mass spectrometry. To acquire more information on the polymerization mechanism, the formation of the actual monomer and the polymerization reaction were studied into more detail. These experiments proved that the polymerization proceeds via a chain-growth mechanism, although not in a controlled way. a Supporting information for this article is available at the bottom of the article's abstract page, which can be accessed from the journal's homepage at http://www.macros.wiley-vch.de, or from the author.-2 - IntroductionPoly(3-alkylthiophene)s (P3ATs) are a class of conjugated polymers that has been intensively studied over the past decades. The discovery by McCullough and Yokozawa of the chain-growth polymerization mechanism of P3ATs has led to a renewed interest in the synthesis of these polymers.[1] This chain-growth mechanism is made possible by the 'ringwalking process' of the Ni-catalyst, whereby the Ni(0) species is transferred intramolecularly along a polymer chain to its end where it oxidatively inserts in the C-Br bond. [2] Due to this mechanism, all polymer chains are equipped with the same end-groups, being a bromine and a hydrogen atom (after quenching with acid). It also allows control of the molar mass by adjusting the feed ratio of the monomer to the Ni-catalyst, and the formation of block copolymers by successive monomer addition.[3]The versatility of the quasi-controlled chain-growth polycondensation has also been demonstrated by the use of other monomers, polymerized with Ni-as well as Pd-catalysts. In this way, polyfluorenes [4] , poly(para-phenylenes) [5] and polypyrroles [3d] have been successfully prepared.If the polythiophene backbone is substituted with an alkoxy instead of an alkyl side-chain, a polymer with different characteristics is obtained. Regioregular HT-coupled poly(3-alkoxythiophene)s (P3AOTs) are electronically different and show a significantly higher  max compared to P3ATs. [6] Their Faraday rotation is much larger (Verdet constant up to 3x10 6 T -1 m -1 ) [7] and their magnetic properties differ [8] . Although their properties are interesting, the polymerization behavior of P3AOTs has never been studied in detail.An important finding in this respect is that starting the polymerization of P3AOT with an otolyl nickel initiator complex results in polymers which mainly bear o-tolyl/hydrogen endgroups -as would be formed by a controlled chain-growth mechanism -but also otolyl/bromine and even small amounts of Br/Br, Br/H and H/H end-groups.[9] Although most -3 -polymers were equipped with the initiator u...

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Highly Conductive, Regioregular Alkoxy-Functionalized Polythiophenes: A New Class of Stable, Low Band Gap Materials

Cited by 114 publications

References 44 publications

Kumada chain-growth polycondensation as a universal method for synthesis of well-defined conjugated polymers

Kumada chain-growth polycondensation as a universal method for synthesis of well-defined conjugated polymers

Nanostructural depth-profile and field-effect properties of poly(alkoxyphenylene-thienylene) Langmuir–Schäfer thin-films

Ni‐Catalyzed Polymerization of Poly(3‐alkoxythiophene)s

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