Chromic effects in poly(3-(10-hexanoyloxydecyl)-2,5-thienylene) as precursor of ω-hydroxydecyl-functionalized polythiophen

Lanzi, Massimiliano; Bertinelli, F.; Costa-Bizzarri, Paolo; Della-Casa, Carlo

doi:10.1002/(sici)1099-1581(199806)9:6<334::aid-pat786>3.0.co;2-7

Cited by 10 publications

(7 citation statements)

References 9 publications

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“…An alternative method to achieve the best mix between these materials is the introduction of polar groups in the side-chain of polythiophene derivatives, for example, hydroxyl or carboxylic acid groups [22] . In general, homopolymers with such high polar groups have limited solubility in common volatile organic solvents because of the strong hydrogen bonding [12,[23][24][25][26][27][28] . The key to improve the solubility of these derivatives is the design of amphiphilic copolymers containing both non-polar and polar side-chains.…”

Section: Introductionmentioning

confidence: 99%

Structural and thermal properties of carboxylic acid functionalized polythiophenes

et al. 2014

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Polythiophenes functionalized with polar groups at the end of side-chain have emerged as an alternative method to obtain good compatibility between this class of conjugated polymers and electron acceptor compounds. The aim is to prevent phase segregation and to improve the efficiency of the polythiophene technological devices. However, homopolymers synthesized from thiophene rings with high polar groups at the end of the side-chain, such as hydroxyl and carboxylic acid groups, are poorly soluble in common volatile organic solvents. We report on a systematic preparation of copolymers of 3-hexylthiophene (HT) and thiophene-3-acetic acid (TAA), using different feed ratios. The chemical structures of the copolymers were confirmed by FTIR and 1 H-NMR. The TAA content in these copolymers were 33, 38 and 54 mol %. HPSEC results did not show any remarkable correlation with TAA contents in the copolymers. In contrast, the thermal analyses showed a decrease in the thermal stability and an increase in rigidity of their backbones, for the copolymers with high amounts of TAA. The solubility and optical property of copolymers were also related to the TAA contents. Thus, the properties of these copolymers can be modulated by a simple control of feed ratio of TAA in the copolymerization.

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Section: Introductionmentioning

confidence: 99%

Structural and thermal properties of carboxylic acid functionalized polythiophenes

et al. 2014

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“…3-(10-Hexanoyloxydecyl)thiophene was synthesized from 3-(10-bromodecyl)thiophene by nucleophilic substitution of the halogen with sodium hexanoate according to the literature. [7] Yield: 84%. 1…”

Section: -(10-hexanoyloxydecyl)thiophene (M1)mentioning

confidence: 99%

“…The structures of polymers and copolymers are shown in Scheme 1. The precursor polymers, poly[3-(10-hexanoyloxydecyl)-2,5-thienylene] (P1), poly{[3-(10-hexanoyloxydecyl)-2,5-thienylene]-co-(3-decyl-2,5-thienylene)} 1 : 9 (CP1), poly{[3-(10-hexanoyloxydecyl)-2,5-thienylene]-co-(3-decyl-2,5-thienylene)} 1 : 1 (CP2) and also poly(3-decyl-2,5-thienylene) (P2) were prepared by the following general procedure: [7] a 1 m solution (20 mL) of anhydrous iron trichloride in dry nitromethane was added dropwise over 20 min at room temperature to a solution of 5 mmol of the monomer (or of the comonomers M1, M2 in molar ratios of 1 : 9 and 1 : 1, respectively, to obtain the copolymer CP1 or CP2, respectively) in carbon tetrachloride. The mixture was stirred for 40 min under a dry nitrogen flow, and then 100 mL of freshly distilled tetrahydrofuran (THF) were added to increase polymer solubility.…”

Section: Synthesis Of Polymersmentioning

confidence: 99%

“…P1: Yield: 75% 1 The hydroxyalkyl polymers, that is poly[3-(10-hydroxydecyl)-2,5-thienylene] (P3), poly{[3-(10-hydroxydecyl)-2,5thienylene]-co-(3-decyl-2,5-thienylene)} 1 : 9 (CP3) and poly{[3-(10-hydroxydecyl)-2,5-thienylene]-co-(3-decyl-2,5thienylene)} 1 : 1 (CP4), were obtained by alkaline methanolysis of the corresponding carboxy precursors P1, CP1 and CP2, according to the procedure described by us in a previous paper. [7] 20 mL of a 0.1 m solution of KOH in MeOH were added under stirring to 1.49 mmol (with respect to repeat unit) of the precursor polymer in 40 mL of THF. The mixture was refluxed for 1 hr and then poured into 600 mL of methanol.…”

Section: Synthesis Of Polymersmentioning

confidence: 99%

“…[4 -6] Notwithstanding, we have managed to obtain completely soluble poly(x-hydroxyalkylthiophenes) via post-functionalization of precursor polymers by way of alkaline methanolysis of some alkyl ester-substituted polythiophenes. [7] A soluble x-hydroxydecyl-functionalized polythiophene has been investigated previously in a number of solvent/non-solvent mixtures. [8] Some peculiar effects have been recorded for the polymer.…”

Section: Introductionmentioning

confidence: 99%

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Anomalous Solvatochromic Effect. Comparison Between Decyl and ω-Hydroxydecyl 3-Substituted Polythiophenes

Lanzi¹,

Della-Casa²,

Costa-Bizzarri³

et al. 2001

Macromol. Chem. Phys.

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The solvatochromic behavior of chloroform solutions of poly(3‐decyl‐2,5‐thienylene), poly[3‐(10‐hydroxydecyl)‐2,5‐thienylene] and their copolymers was studied by the addition of the non‐solvent methanol. A reversed chromic transformation was found associated with the content of the hydroxyalkyl substituent. This anomalous effect was investigated using a number of non‐solvents, in particular aliphatic alcohols from methanol up to decanol. In the case of a chloroform/methanol mixture, which gives the maximum anomalous effect, the effect produced by temperature variation was also examined. An explanation based on a molecular approach was attempted.

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Photoactive Polythiophene:Titania Hybrids with Excellent Miscibility for Use in Polymer Photovoltaic Cells

Chang

Wang

2008

Macromol. Rapid Commun.

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A series of poly{(3‐hexylthiophene)‐co‐[3‐(6‐hydroxyhexyl)thiophene]}:titania (P3HT‐OH:TiO2) hybrids were synthesized via the in situ polycondensation of titanium (IV) n‐butoxide in the presence of P3HT‐OH. Introducing a hydroxyl moiety onto the side‐chain of poly(3‐hexylthiophene) (P3HT) significantly promotes the polymer‐titania interaction, resulting in the formation of homogeneous hybrid colloids. The UV‐vis spectra of P3HT‐OH:TiO2 films demonstrate that TiO2 markedly affects the stacking structure and the chain conformation of P3HT‐OH. The maximum absorption wavelength of these hybrid materials can be tailor‐made by merely varying the weight percentage of TiO2. Moreover, P3HT‐OH:TiO2 can be further utilized as an efficient compatibilizer in preparing photoactive P3HT:P3HT‐OH:TiO2 films with excellent miscibility. The photovoltaic cell based on such a hybrid exhibited a 2.4‐fold higher value of power‐conversion efficiency compared to the cell based on P3HT:TiO2.

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Chromic effects in poly(3-(10-hexanoyloxydecyl)-2,5-thienylene) as precursor of ω-hydroxydecyl-functionalized polythiophen

Cited by 10 publications

References 9 publications

Structural and thermal properties of carboxylic acid functionalized polythiophenes

Structural and thermal properties of carboxylic acid functionalized polythiophenes

Anomalous Solvatochromic Effect. Comparison Between Decyl and ω-Hydroxydecyl 3-Substituted Polythiophenes

Photoactive Polythiophene:Titania Hybrids with Excellent Miscibility for Use in Polymer Photovoltaic Cells

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