End-group modification of regioregular poly(3-alkylthiophene)s

Langeveld-Voss, Bmw Bea; Janssen, Raj René; Spiering, A. J. H.; Dongen, Jlj Joost van; Vonk, EC Erik; Claessens, HA Henk

doi:10.1039/a908848b

Cited by 52 publications

(41 citation statements)

References 11 publications

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“…Our group 15 and others 14 have recently reported that HT-PATs synthesized through either the McCullough 2 or Rieke 3 route usually have three types of end group composition due to the presence of side reactions in the cross-coupling polymerization. The polymer chains can be terminated with a proton at one end and a bromine at the other end (H/Br), a proton at both ends (H/H), or a bromine at both ends (Br/Br).…”

Section: Resultsmentioning

confidence: 99%

End Group Modification of Regioregular Polythiophene through Postpolymerization Functionalization

2002

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HT-poly(3-hexylthiophenes) (HT-PHT) with H/Br end group composition were prepared via a modified McCullough method using anhydrous ZnCl2 for the transmetalation step. These bromineterminated HT-PHT can be end group modified at the ω end through a cross-coupling reaction with thienylzinc compounds bearing a THP-protected hydroxy or STABASE-protected amino groups. After deprotection, HT-PHTs with -OH or -NH2 functional groups at the ω end were obtained. In addition, HT-PHT with pure H/H end group composition were also modified by treatment with Vilsmeier reagent and functionalized with formaldehyde groups at both the R and ω chain ends. Reduction of the formaldehyde groups produced the HT-PHT diol. MALDI-TOF is a powerful tool to monitor each step of these end group functionalizations.

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Section: Resultsmentioning

confidence: 99%

End Group Modification of Regioregular Polythiophene through Postpolymerization Functionalization

2002

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“…Contribution of the different monomeric sequences to the peaks assigned to a-CH 2 cannot be ruled out a priori, but this effect generally becomes important only when distinct sequences of the two repeating units (blocks) are generated along the polymeric backbone, thus leading to a duplication of the two aforementioned signals. [29][30][31][32] In fact, in these PT systems, the two peaks ascribable to the a-CH 2 belonging to the two sequences, determined by the homo-coupling of a single type of monomer, while although very close together, can nevertheless be distinguished. [33] Since the peak at 0.96 ppm may be exclusively ascribed to the -CH 3 of the plasticizing comonomer and the two peaks ascribable to the methylenic protons a to the thiophenic ring are common to both comonomers, an azo-dye content of 27% may be estimated, on the basis of their normalized integrated intensity ratios (see Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Novel Polymers with Inherent Conductivity and Enhanced Second‐Order NLO Activity

Lanzi¹,

Paganin²,

Cesari³

2008

Macro Chemistry & Physics

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A new polythiophene derivative bearing an azobenzene substituent at the end of a ethylenic side‐chain was synthesized and characterized by FT‐IR spectroscopy, 1H and 13C NMR spectroscopy, DSC, TGA, XRD, and UV‐vis spectroscopy. Its electrical conductivity was measured and its second‐order NLO activity was by SHG. Structure‐property relations were elucidated by comparison with a similar polymer only partially substituted by the NLO‐active chromophore. The molecular design of the chromophoric system allows high and stable non‐linear coefficients d33 to be obtained, making these polymers suitable for the construction of second‐harmonic generators with improved efficiency and life‐time.

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“…[36][37][38] This remarkable property of P3HT has led to numerous new materials including block copolymers capable of generating nanostructures. 35 39 Synthesis of P3HT by the GRIM or McCullough methods produces a polymer with two different end groups, H/Br and H/H.…”

Section: End Group Functionalization Of Regioregular P3htmentioning

confidence: 99%

Poly(3-Hexylthiophene) Nanostructured Materials for Organic Electronics Applications

Bhatt¹,

Magurudeniya²,

Rainbolt³

et al. 2014

j. nanosci. nanotech.

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Semiconducting polymers have been developed during the last few decades and are currently used in various organic electronics applications. Regioregular poly(3-hexylthiophene) (P3HT) is the most employed semiconducting polymer for organic electronics applications. The development of living Grignard metathesis polymerization (GRIM) allowed the synthesis of P3HT with well-defined molecular weights and functional end groups. A large number of block copolymers containing P3HT have been reported, and their opto-electronic properties have been investigated. The performance of P3HT homopolymer and block copolymers in field-effect transistors and bulk heterojunction solar cells are discussed in this review. The morphology of the P3HT materials is also discussed.

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End-group modification of regioregular poly(3-alkylthiophene)s

Cited by 52 publications

References 11 publications

End Group Modification of Regioregular Polythiophene through Postpolymerization Functionalization

End Group Modification of Regioregular Polythiophene through Postpolymerization Functionalization

Novel Polymers with Inherent Conductivity and Enhanced Second‐Order NLO Activity

Poly(3-Hexylthiophene) Nanostructured Materials for Organic Electronics Applications

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