Design and synthesis of aniline-appended P3HT for single step covalent functionalisation of carbon nanotubes

Klein, Felipe Wasem; Lamps, Jean-Philippe; Raoui, Mohamed; Paillet, Matthieu; Sauvajol, Jean‐Louis; Mésini, Philippe J.; Petit, P.

doi:10.1039/d0py01147a

Cited by 2 publications

(9 citation statements)

References 36 publications

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“…This ratio corresponds to 780 mg of SWNTs per mmol of PDTcoADT. As shown previously [15], for the hexyl analogue, the critical ratio is of 230 mg of SWNTs per mmol of PHTcoAHT. It shows that the dodecyl analogue solubilizes 3.3 times more SWNTs than the hexyl analogue.…”

Section: Formation and Study Of The Non-covalent Copolymer/swnt Hybridssupporting

confidence: 60%

“…We aim at synthesizing a copolymer based on a poly(3-alkylthiophene) with side chains bearing aniline groups. As we have shown previously [15], when the alkyl chain is hexyl, this polymer is able to bind non-covalently with SWNTs, to form soluble polymer/SWNT hybrid complexes. The same hybrids heated in the presence of isoamyl nitrite react according to Tour's reaction: the aniline groups are transformed into a transitory diazonium that reacts with SWNTs to attach the phenyl of the aniline covalently to the SWNTs walls (Scheme 1).…”

Section: Design Of the Compoundsmentioning

confidence: 60%

“…The choice of the iodine in position 5 adds a step to the synthesis of the monomer; but as shown by Catala et al [22], it increases the regioselectivity of the metallation and subsequent polymerization. Moreover, both monomers have close reactivity, and we have shown that the composition of the polymer follows that of the feed mixture monomer [15], which suggests that the yielded polymer is a random copolymer. By the GRIM method, Yang et al have also obtained random copolymers from thiophene based monomers with even larger structural differences than 1 and 2 [23].…”

Section: Syntheses Of the Monomers And Polymersmentioning

confidence: 71%

“…Size exclusion chromatography: analytical and preparative SEC were carried out according the previously described procedure [15].…”

Section: General Methodsmentioning

confidence: 99%

“…In order to overtake this problem, we propose a functionalization in one-step by attaching the functional group directly to the polymer chain. In our previous work, [15] we have synthesized PHTcoAHT, a statistical copolymer based on poly(3-hexylthiophene) and bearing aniline side groups. This copolymer forms non-covalent hybrids with singlewalled carbon nanotubes (SWNTs) and can also react with the SWNTs in one step to form covalent hybrids.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a Poly(3-dodecylthiophene) Bearing Aniline Groups for the Covalent Functionalization of Carbon Nanotubes

et al. 2021

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The functionalization of carbon nanotubes by polymers necessitates two steps, first their modification by oxidizing them or by covalently attaching small compounds to them, then the growth of the polymer chains from these anchors or their grafting onto them. In order to better control the process and the rate of functionalization, we develop polymers able to covalently react with the carbon nanotubes by their side chains in one step. We describe the synthesis of a copolymer of dodecylthiophene and its analogue bearing an aniline group at the end of the dodecyl side chain. This copolymer can functionalize single-walled carbon nanotubes (SWNTs) non-covalently and disperse more SWNTs than its hexyl analogues. UV-Vis and fluorescence spectroscopies show that in these non-covalent hybrids, the polymer forms p-stacked aggregates on the SWNTs. The non-covalent hybrids can be transformed into covalent ones by diazonium coupling. In these covalent hybrids the polymer is no longer p-stacked. According to Raman spectroscopy, the conformation of the poly(3-hexylthiophene) backbone is more ordered in the non-covalent hybrids than in the covalent ones.

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Section: Formation and Study Of The Non-covalent Copolymer/swnt Hybridssupporting

confidence: 60%

Section: Design Of the Compoundsmentioning

confidence: 60%

Section: Syntheses Of the Monomers And Polymersmentioning

confidence: 71%

“…Size exclusion chromatography: analytical and preparative SEC were carried out according the previously described procedure [15].…”

Section: General Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of a Poly(3-dodecylthiophene) Bearing Aniline Groups for the Covalent Functionalization of Carbon Nanotubes

et al. 2021

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Molecular Weight-Dependent Physical and Photovoltaic Properties of Poly(3-alkylthiophene)s with Butyl, Hexyl, and Octyl Side-Chains

Nguyen

Song

et al. 2021

Polymers

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A series of poly-3-alkylthiophenes (P3ATs) with butyl (P3BT), hexyl (P3HT), and octyl (P3OT) sidechains and well-defined molecular weights (MWs) were synthesized using Grignard metathesis polymerization. The MWs of P3HTs and P3OTs obtained via gel permeation chromatography agreed well with the calculated MWs ranging from approximately 10 to 70 kDa. Differential scanning calorimetry results showed that the crystalline melting temperature increased with increasing MWs and decreasing alkyl side-chain length, whereas the crystallinity of the P3ATs increased with the growth of MWs. An MW-dependent red shift was observed in the UV–Vis and photoluminiscence spectra of the P3ATs in solution, which might be a strong evidence for the extended effective conjugation occurring in polymers with longer chain lengths. The photoluminescence quantum yields of pristine films in all polymers were lower than those of the diluted solutions, whereas they were higher than those of the phenyl-C61-butyric acid methyl ester-blended films. The UV–Vis spectra of the films showed fine structures with pronounced red shifts, and the interchain interaction-induced features were weakly dependent on the MW but significantly dependent on the alkyl side-chain length. The photovoltaic device performances of the P3BT and P3HT samples significantly improved upon blending with a fullerene derivative and subsequent annealing, whereas those of P3OTs mostly degraded, particularly after annealing. The optimal power conversion efficiencies of P3BT, P3HT, and P3OT were 2.4%, 3.6%, and 1.5%, respectively, after annealing with MWs of ~11, ~39, and ~38 kDa, respectively.

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Design and synthesis of aniline-appended P3HT for single step covalent functionalisation of carbon nanotubes

Abstract: The synthesis of a copolymer derived from poly(3-hexylthiophene), one of the monomers bearing an aniline group, is described. Like the homopolymer, this copolymer is able to functionalise carbon nanotubes by...

Cited by 2 publications

References 36 publications

Synthesis of a Poly(3-dodecylthiophene) Bearing Aniline Groups for the Covalent Functionalization of Carbon Nanotubes

Synthesis of a Poly(3-dodecylthiophene) Bearing Aniline Groups for the Covalent Functionalization of Carbon Nanotubes

Molecular Weight-Dependent Physical and Photovoltaic Properties of Poly(3-alkylthiophene)s with Butyl, Hexyl, and Octyl Side-Chains

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