Layered structure with side chain crystallinity in undoped poly(3-alkyl thiophenes)

Ho, Kachun; Bartus, Jan; Levón, Kalle; Mao, Jingjing; Zheng, Wenyue; Laakso, J.; Taka, T.

doi:10.1016/0379-6779(93)90962-v

Cited by 30 publications

(27 citation statements)

References 2 publications

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“…For the series of polymers bearing a nonafluorobutyl chain (i.e., P(Th- m ,4) ) or heptadecafluorooctyl chain (i.e., p(Th- m ,8) ) the melting points decrease upon increasing the length of the hydrocarbon spacer (increasing m ). This is consistent with the effect of side chain lengths of poly(3-alkylthiophene)s on the melting point . However, for p(Th-11,4) there are two endothermic peaks (87 and 128 °C).…”

Section: Resultssupporting

confidence: 84%

Synthesis and Oxidative Polymerization of Semifluoroalkyl-Substituted Thiophenes

et al. 1999

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A series of semifluorinated 3-alkylthiophenes ((3-thienyl-(CH2) m -CF2) n F, Th- m , n ) were prepared by addition of perfluoroalkyl iodides to 3-(ω-alken-1-yl)thiophenes followed by treatment with NaBH4. Chemical and electrochemical oxidation gave the corresponding substituted polythiophenes. The fluorinated side chains have dramatic effects on the conjugation of the polythiophene backbone and thermal phase bahavior. Since the perfluoroalkyl parts of the side chains are approximately the same size as alkyl parts, and the electron-withdrawing effect of the fluorine atoms is insulated from the thiophene ring by a hydrocarbon spacer, these effects are ascribed to interactions between side chains. Microsegregation arising from the immiscibility of fluorocarbon and hydrocarbon segments of semifluorinated alkyl-substituted polymers provides for control of supermolecular architecture. The new 3-(semifluorinated alkyl)thiophenes will serve as comonomers in the design of self-organizing conjugated polymers.

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Section: Resultssupporting

confidence: 84%

Synthesis and Oxidative Polymerization of Semifluoroalkyl-Substituted Thiophenes

et al. 1999

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“…The length of alkyl chains at the third position of the thiophene ring, in the polymerization of the thiophene monomers, has been found to significantly influence the effective conjugation length. Indeed, long alkyl chains are more flexible and accommodating, such as dodecyl chains, and lead to a larger effective conjugation length than the shorter ones [ 66 , 67 ]. As such, the long alkyl chains at the third position of the thiophene ring, in M4 110 must have favoured effective polymerization, and thus, the conjugation length observed.…”

Section: Resultsmentioning

confidence: 99%

New Layered Polythiophene-Silica Composite Through the Self-Assembly and Polymerization of Thiophene-Based Silylated Molecular Precursors

et al. 2018

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A new layered hybrid polythiophene-silica material was obtained directly by hydrolysis and polycondensation (sol-gel) of a silylated-thiophene bifunctional precursor, and its subsequent oxidative polymerization by FeCl3. This precursor was judiciously designed to guarantee its self-assembly and the formation of a lamellar polymer-silica structure, exploiting the cooperative effect between the hydrogen bonding interactions, originating from the ureido groups and the π-stacking interactions between the thiophene units. The lamellar structure of the polythiophene-silica composite was confirmed by X-ray powder diffraction (XRD) and transmission electron microscopy (TEM) analyses. The solid-state nuclear magnetic resonance (NMR), UV-Vis, and photoluminescence spectra unambiguously indicate the incorporation of polythiophene into the silica matrix. Our work demonstrates that using a polymerizable silylated-thiophene precursor is an efficient approach towards the formation of nanostructured conjugated polymer-based hybrid materials.

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“…Thus, the addition of ran‐P3DT, which is not able to adopt an ordered main chain structure, to the coatings produces an improvement of both the mechanical properties and the anticorrosive properties not only with respect to original paints but also with respect the paints modified with reg‐P3DT. It should be remarked that the structure of the decyl side groups is very similar for both reg‐P3DT and ran‐P3DT7–10, 14–17 indicating that, when these two polymers are used as additives of conventional organic coatings, the differences in their behavior must be attributed exclusively to the main chain stereoregularity. Thus, the amorphous nature of ran‐P3DT induces favorable interactions with the resin allowing their complete miscibility, this feature being responsible for the excellent results obtained when this polymer is used as additive.…”

Section: Resultsmentioning

confidence: 99%

Poly(3‐alkylthiophene)s as anticorrosive additive for paints: Influence of the main chain stereoregularity

Iribarren

Ocampo

Armelín

et al. 2008

J of Applied Polymer Sci

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The influence of the main chain stereoregularity on the properties of poly(3-decylthiophene-2,5-diyl) as anticorrosive additive of conventional organic coatings have been examined. For this purpose a small concentration (0.3% w/w) of regiorandom and regioregular conducting polymers were added to alkyd, epoxy, and polyurethane paints typically used in marine environments. The Young's modulus and the elongation at break of the alkyd and epoxy coatings modified with the regiorandom conducting polymer were significantly better than those of the films generated with the original paints, evidencing a very favorable interaction between the additive and the resins. On the other hand, the anticorrosive properties imparted by the modified paints are better when the conducting polymer is regiorandom than when it is regioregular, although even the degree of protection provided by all the modified coatings was higher than that of the original ones.

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Layered structure with side chain crystallinity in undoped poly(3-alkyl thiophenes)

Cited by 30 publications

References 2 publications

Synthesis and Oxidative Polymerization of Semifluoroalkyl-Substituted Thiophenes

Synthesis and Oxidative Polymerization of Semifluoroalkyl-Substituted Thiophenes

New Layered Polythiophene-Silica Composite Through the Self-Assembly and Polymerization of Thiophene-Based Silylated Molecular Precursors

Poly(3‐alkylthiophene)s as anticorrosive additive for paints: Influence of the main chain stereoregularity

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