Combination of phosphonium and ammonium pendant groups in cationic conjugated polyelectrolytes based on regioregular poly(3-hexylthiophene) polymer chains

Hladysh, Sviatoslav; Murmiliuk, Anastasiia; Vohlı́dal, Jiřı́; Havlı́ček, David; Sedlařík, Vladimír; Štěpánek, Miroslav; Zednı́k, Jiřı́

doi:10.1016/j.eurpolymj.2018.01.029

Cited by 14 publications

(23 citation statements)

References 54 publications

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“…The occurrence of the post-functionalization with tributylphosphine of PT6Br and P[(T6Br)-co-(T6F)], to give PT6buP + and P[(T6buP + )-co-(T6F)], respectively, was verified by both 1 H-NMR and 13 C-NMR, as well as 31 P-NMR spectroscopy. In particular, when analyzing 1 H-NMR spectra, the presence of a broad multiplet at 2.75 ppm (P[(T6buP + )-co-(T6F)] spectrum, Figure 2B) and a broad triplet at 2.24 ppm (PT6buP + spectrum, Figure S1) can be attributed to the eight methylenic protons in αand α'-position to the cationic phosphine group.…”

Section: Nmr Characterizationmentioning

confidence: 94%

“…All the synthesized products were characterized by 1 H-NMR and 13 C-NMR spectrometry to evaluate their chemical structure and purity degree (see Supporting Information for 1 H-NMR and 13 C-NMR spectra).…”

Section: Nmr Characterizationmentioning

confidence: 99%

“…1 H-NMR, 13 C-NMR and 31 P-NMR were recorded on a Varian Mercury Plus 400 spectrometer using TMS as a reference. IR spectra were taken on Ge or KBr disks using a Perkin Elmer Spectrum One spectrophotometer.…”

Section: Measurementsmentioning

confidence: 99%

“…Polymers 2021, 13, 1640 2 of 19 with an electron acceptor (EA, usually a fullerene derivative) material. The obtained heterojunction provides a high interface area between the two components, while promoting an efficient generation and transport of free-charge carriers.…”

Section: Introductionmentioning

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: 94%

Section: Nmr Characterizationmentioning

confidence: 99%

Section: Measurementsmentioning

confidence: 99%

Section: Introductionmentioning

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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“…The key starting conjugated polymer precursor poly[3‐(6‐bromohexyl)thiophene‐2,5‐diyl], abbreviated as PHT‐Br , was synthesized according to the procedure frequently used in our research group . High head‐to‐tail regioregularity (more than 90% of the aforementioned polymer) was achieved using the Grignard metathesis (GRIM) polymerization method developed by the McCullough’s group .…”

Section: Methodsmentioning

confidence: 99%

Attachment of a 1,8‐Naphthalimide Moiety to a Conjugated Polythiophene Efficiently Improves the Sensing Abilities of Naphthalimide‐Based Materials

Hladysh

Murmiliuk

Vohlı́dal

et al. 2018

Macro Chemistry & Physics

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A novel polythiophene‐based conjugated polymer bearing 1,8‐naphthalimide‐based pendants is prepared by a two‐step modification of regioregular poly[3‐(6‐bromohexyl)thiophene] involving a nucleophilic substitution reaction of the bromide end‐groups with sodium azide followed by a robust, copper‐catalyzed Huisgen click reaction with a novel 1,8‐naphthalinmide derivative containing an active, N‐substituted propyne group. Both the polymer and the highly luminescent‐active synthesized dye are extensively studied in solution by UV–vis spectroscopy, photoluminescence, NMR, light‐scattering and isothermal titration calorimetry. The materials prepared are considered potential chemosensors for different transition metals, such as Fe2+, Co2+, Ni2+, Cu2+, Zn2+, and Cd2+. Luminescence quenching shows that these materials have a higher sensitivity to Fe2+ than to the other metal ions tested. Moreover, the 1,8‐naphthalimide‐based conjugated polymer is more efficiently quenched by Fe2+ metal ions, at a significantly lower concentration and with a higher binding constant than its parent 1,8‐naphthalimide derivative, thus indicating a high potential for sensor development.

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Effects of Water/Alcohol Soluble Cationic Polythiophenes as Cathode Interlayers for Eco‐Friendly Solar Cells

Quadretti

Marinelli

Salatelli

et al. 2023

Macro Chemistry & Physics

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Three new ionic polythiophene derivatives, soluble in polar solvents, are synthesized with good yields using simple, low-cost, and straightforward procedures. They are investigated as interfacial cationic conjugated polyelectrolyte (CPE) layers for halogen-free bulk heterojunction polymeric solar cells, based on a water-soluble electron-donor polymer (poly[3-(6-diethanolaminohexyl)thiophene]) and a water-soluble electron-acceptor fullerene derivative (malonodiserinolamide fullerene). The simple insertion of the CPE interlayer between the active layer and the aluminum cathode dramatically increases the power conversion efficiency of the final device up to nearly 5%, resulting from a decrease of the electrode work function, improved electron extraction, and optimization of the morphology of the layers. The obtained results demonstrate that the incorporation of CPE layer is a powerful and convenient methodology for the development of highly efficient and eco-friendly processable polymeric solar cells.

show abstract

Combination of phosphonium and ammonium pendant groups in cationic conjugated polyelectrolytes based on regioregular poly(3-hexylthiophene) polymer chains

Cited by 14 publications

References 54 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

Attachment of a 1,8‐Naphthalimide Moiety to a Conjugated Polythiophene Efficiently Improves the Sensing Abilities of Naphthalimide‐Based Materials

Effects of Water/Alcohol Soluble Cationic Polythiophenes as Cathode Interlayers for Eco‐Friendly Solar Cells

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