Synthesis by post-polymerization functionalization of sensitive polythiophenes for selective chemo-recognition purposes

Lanzi, Massimiliano; Costa-Bizzarri, Paolo; Paganin, Luisa; Cesari, Gaia

doi:10.1016/j.reactfunctpolym.2007.01.007

Cited by 12 publications

(11 citation statements)

References 22 publications

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“…Moreover, when 13 C-NMR spectra of PT6buP + and P[(T6buP + )-co-(T6F)] (Figures S2 and S3) are compared with those of the corresponding precursor polymers PT6Br and P[(T6Br)-co-(T6F)] (Figures S4 and S5), a further confirmation that the post-functionalization took place is obtained. In detail, passing from the PT6Br to PT6buP + spectrum, the signal at 34.59 ppm (CH 2 Br) is missing, while three new signals appear at 19.52 (CH 2 P + ), 19.04 (P + CH 2 ), and 13.87 (CH 3 ) ppm. A similar result is obtained from the comparison of the spectra of P[(T6Br)-co-(T6F)] and P[(T6buP + )-co-(T6F)]: in this case, the signal at 32.03 ppm (CH 2 Br) present in the brominated copolymer spectrum is completely missing in that of the watersoluble copolymer and replaced by the signals belonging to the tributylphosphonium group at 19.37 (CH 2 P + ), 18.90 (P + CH 2 ), and 13.80 (CH 3 ) ppm.…”

Section: Nmr Characterizationmentioning

confidence: 92%

“…Iodine resublimed (I 2 ) and magnesium (Mg) for Grignard were purchased from Merck (Darmstadt, Germany). 2,5-Dibromo-3-(6bromohexyl)thiophene (2,, as the starting monomer, was synthesized according to the method reported in the literature [19,20]. Just before use, the solvent used for the Grignard Metathesis Polymerization (GRIM) was dried with a sodium-potassium alloy under reflux and stored over molecular sieves.…”

Section: Methodsmentioning

confidence: 99%

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Influence of the Active Layer Structure on the Photovoltaic Performance of Water-Soluble Polythiophene-Based Solar Cells

et al. 2021

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A new side-chain C60-fullerene functionalized thiophene copolymer bearing tributylphosphine-substituted hexylic lateral groups was successfully synthesized by means of a fast and effective post-polymerization reaction on a regioregular ω-alkylbrominated polymeric precursor. The growth of the polymeric intermediate was followed by NMR spectrometry in order to determine the most convenient reaction time. The obtained copolymer was soluble in water and polar solvents and was used as a photoactive layer in single-material organic photovoltaic (OPV) solar cells. The copolymer photovoltaic efficiency was compared with that of an OPV cell containing a water-soluble polythiophenic homopolymer, functionalized with the same tributylphosphine-substituted hexylic side chains, in a blend with a water-soluble C60-fullerene derivative. The use of a water-soluble double-cable copolymer made it possible to enhance the control on the nanomorphology of the active blend, thus reducing phase-segregation phenomena, as well as the macroscale separation between the electron acceptor and donor components. Indeed, the power conversion efficiency of OPV cells based on a single material was higher than that obtained with the classical architecture, involving the presence of two distinct ED and EA materials (PCE: 3.11% vs. 2.29%, respectively). Moreover, the synthetic procedure adopted to obtain single material-based cells is more straightforward and easier than that used for the preparation of the homopolymer-based BHJ solar cell, thus making it possible to completely avoid the long synthetic pathway which is required to prepare water-soluble fullerene derivatives.

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Section: Nmr Characterizationmentioning

confidence: 92%

Section: Methodsmentioning

confidence: 99%

Influence of the Active Layer Structure on the Photovoltaic Performance of Water-Soluble Polythiophene-Based Solar Cells

et al. 2021

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“…2,5‐Dibromo‐3‐(6‐bromohexyl)thiophene was prepared by adapted procedure described in ref. 17 (yield 91%), 1 H NMR (400 MHz, DMSO‐ d 6 , 25 °C, ppm): 7.14 (s, 1 H 3 ), 3.51 (t, 2 H 10 , J = 6.7), 2.53 (m, 2H 5 , signal overlaps with the solvent signal), 1.79 (m, 2 H 9 ), 1.52 (m, 2 H 6 ), 1.40 (m, 2 H 8 ), 1.28 (m, CH 7 ). 13 C NMR (100.58 MHz, DMSO‐ d 6 , 25 °C, ppm): 143.26 C q 4 , 131.9 C 3 , 109.9 C q 1 , 107.5 C q 2 , 40.0 C 5 (overlapped with solvent signal), 35.0 C 10 , 32.1 C 9 , 28.7 C 6 .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and properties of cationic polyelectrolyte with regioregular polyalkylthiophene backbone and ionic‐liquid like side groups

Bondarev

Zednı́k

Šloufová

et al. 2010

J. Polym. Sci. A Polym. Chem.

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High-regioregular poly{3-[6-(1-methylimidazolium-3yl)hexyl]thiophene-2,5-diyl bromide}, PMHT-Br, has been prepared by reaction of high-regioregular (above 92%) poly[3-(6bromohexyl)thiophene-2,5-diyl] with 1-methylimidazole. PMHT-Br is soluble in water and water miscible solvents such as methanol, DMSO and shows solvatochromism; k max (nm): 423 (H 2 O); 435 (MeOH); 452 (DMSO). Increased absorption band broadening observed for aqueous solution as well as NMR spectra in D 2 O suggests a micelle-like structure of PMHT-Br molecules in these solutions: poly(3-hexylthiophene) core and 1-methylimidazolium bromide shell. Despite the disturbing effect of ionic groups, the solid-state PMHT-Br shows absorption maximum at 520 nm, the band edge at 660 nm (ca. 1.9 eV), and fluorescence emission with maximum at 635 nm, in a good agreement with the polymer regioregularity. Fluorescence emission maxima: k em (nm): 598 (H 2 O); 562 (MeOH); 574 (DMSO), occur in a vicinity of corresponding adsorption band edges. Plot of electrical conductivity of PMHT-Br (measured under the dynamic vacuum conditions, 5 Â 10 À5 Pa) versus 1/T shows a break at about 70 C same as the temperature dependence of k max of the solid PMHT-Br. These breaks indicate an increase in the mobility of polymer segments and ions within PMHT-Br; however, a thermal analysis did not provide solid evidence for it. V C 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3073-3081, 2010 INTRODUCTION Conjugated polyelectrolytes (CPEs) show unique optical and electrical properties together with good solubility in water making possible processing of these polymers from aqueous solutions. As CPEs exhibit both electronic and ionic conductivity, they can be used as layers reducing electron injection barrier from metal electrodes, such as aluminum and gold electrodes into polymer in various optoelectronic applications 1 and also as new solid polyelectrolytes with increased room-temperature electrical conductivity. 2,3 Solubility in aqueous environment and water-miscible solvents also substantially simplifies preparation of the composites of CPEs with noble-metal nanoparticles, which exhibit the effect of local enhancement of electromagnetic field. 4 Another possible application field of CPEs is their use as water-soluble sensing agents for the detection of ions, nucleic acids, and some proteins on the basis of changes in UV/vis and photoluminescence spectra induced by conformational changes of CPE macromolecules caused by their complexation with oppositely charged analyte species. 5-10

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“…The films' thickness was measured by means of a mechanical profilometer and was about 0.15 mm. The values of specific electrical conductivity of OCT and PQ1 are slightly higher if compared to other previously synthesized PATs [28,29] but they, however, fall within the values typical of insulating materials.…”

Section: Electrical Measurementsmentioning

confidence: 49%

New photoactive oligo- and poly-alkylthiophenes

Lanzi

Paganin

Caretti

2008

Polymer

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Synthesis by post-polymerization functionalization of sensitive polythiophenes for selective chemo-recognition purposes

Cited by 12 publications

References 22 publications

Influence of the Active Layer Structure on the Photovoltaic Performance of Water-Soluble Polythiophene-Based Solar Cells

Influence of the Active Layer Structure on the Photovoltaic Performance of Water-Soluble Polythiophene-Based Solar Cells

Synthesis and properties of cationic polyelectrolyte with regioregular polyalkylthiophene backbone and ionic‐liquid like side groups

New photoactive oligo- and poly-alkylthiophenes

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