Synthesis of substituted oligothiophenes and X-ray crystal structures of 3′-methyl-2,2′∶5′,2″-terthiophene, 3,3″-dimethyl-2,2′∶5′,2″-terthiophene and 5′-(2-thienyl)-2,2′∶3′,2″-terthiophene

Chaloner, Penny A.; Gunatunga, S. R.; Hitchcock, Peter B.

doi:10.1039/a607254b

Cited by 57 publications

(51 citation statements)

References 26 publications

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“…[19][20][21] The random copolymers were prepared following the so-called Grignard metathesis procedure according to McCullough et al (Scheme 1). [22] The resulting pristine copolymers, after a standard work-up procedure of the reaction mixture, were further purified by subsequent solvent extraction steps with methanol, hexane, dichloromethane and chloroform.…”

Section: Experimental Partmentioning

confidence: 99%

The Influence of Interchain Branches on Solid State Packing, Hole Mobility and Photovoltaic Properties of Poly(3‐hexylthiophene) (P3HT)

Bilge

Adamczyk

et al. 2007

Macromol. Rapid Commun.

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The hole mobility and power conversion efficiency of bulk heterojunction solar cells based on P3HT‐type donor polymers and the soluble fullerene derivative [6,6]‐phenyl C61 butyric acid methyl ester (PCBM) as an acceptor both show a strong sensitivity to the introduction of interchain branches into the P3HT backbones. Branched B‐P3HT copolymers display a distinctly decreased hole mobility and reduced solar cell power conversion efficiency with increasing amount of interchain 3.3′‐bithiophene branches within the polythiophene macromolecules. The results illustrate the primary importance of proper solid state packing towards optimum charge transport and solar cell performance.

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Section: Experimental Partmentioning

confidence: 99%

The Influence of Interchain Branches on Solid State Packing, Hole Mobility and Photovoltaic Properties of Poly(3‐hexylthiophene) (P3HT)

Bilge

Adamczyk

et al. 2007

Macromol. Rapid Commun.

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“…The first two steps were performed according to literature and consisted of making the methyl thiophene Grignard reagent 1 , which was then coupled to dibromobithiophene in a nickel-catalyzed reaction to form quaterthiophene 2 52,53. Subjecting the alpha-free quaterthiophene 2 to Vilsmeier formylation followed by reduction produced the bismethoxy-dimethyl quarterthiophene (bMdMQT) 4 .…”

Section: Resultsmentioning

confidence: 99%

Toward a Biocompatible and Biodegradable Copolymer Incorporating Electroactive Oligothiophene Units

2008

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As part of an ongoing effort to develop biocompatible, biodegradable conducting polymers, we report here the synthesis and characterization of a novel copolymer, 5,5"'bishydroxymethyl-3,3"'-dimethyl-2,2':5',2":5",2"'-quaterthiophene-co-adipic acid polyester (QAPE). This system was designed so as to incorporate alternating electroactive quaterthiophene units and biodegradable ester units into one macromolecular framework, while allowing for facile preparation of the polymer via a polycondensation reaction. In agreement with the design expectations, the ester groups were found to be incorporated into the polymer between the quaterthiophene subunits, as inferred from standard chemical and spectroscopic analyses. QAPE exhibited redox activity as detected by cyclic voltammetry and a new red-shifted absorption peak upon doping, providing support for the notion that the quaterthiophene units maintain electroactivity after incorporation into the QAPE polymer framework. The degradation, likely through surface erosion, of this polymer in the presence of cholesterol esterase was confirmed by the detection of a fluorescence signal at wavelengths corresponding to the quaterthiophene subunit and comparisons to appropriate controls. In vitro cytocompatability studies, carried out over 48 h, indicate that the QAPE polymer is nontoxic to Schwann cells.

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“…3-Hexylthiophene was synthesized in this laboratory by following the method of literature reported by Chaloner et al[43].All other reagents and solvents used in this work were purchased from Shanghai Reagent Co., China. Before use, toluene and tetrahydrofuran were refluxed over sodium and then distilled.…”

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confidence: 99%

Nanostructured thermosets containing π-conjugated polymer nanophases: Morphology, dielectric and thermal conductive properties

Cong

et al. 2015

Polymer

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Synthesis of substituted oligothiophenes and X-ray crystal structures of 3′-methyl-2,2′∶5′,2″-terthiophene, 3,3″-dimethyl-2,2′∶5′,2″-terthiophene and 5′-(2-thienyl)-2,2′∶3′,2″-terthiophene

Abstract: A range of substituted oligothiophenes has been prepared and characterised. Crystal structures were determined for three substituted terthiophenes. Both in solution and in the solid state, syn-conformers were found to be populated to a greater extent than expected.

Cited by 57 publications

References 26 publications

The Influence of Interchain Branches on Solid State Packing, Hole Mobility and Photovoltaic Properties of Poly(3‐hexylthiophene) (P3HT)

The Influence of Interchain Branches on Solid State Packing, Hole Mobility and Photovoltaic Properties of Poly(3‐hexylthiophene) (P3HT)

Toward a Biocompatible and Biodegradable Copolymer Incorporating Electroactive Oligothiophene Units

Nanostructured thermosets containing π-conjugated polymer nanophases: Morphology, dielectric and thermal conductive properties

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