Novel conjugated polyelectrolytes based on polythiophene bearing phosphonium side groups

Hladysh, Sviatoslav; Bondarev, Dmitrij; Svoboda, Ján; Vohlı́dal, Jiřı́; Vrbata, David; Zednı́k, Jiřı́

doi:10.1016/j.eurpolymj.2016.07.019

Cited by 14 publications

(14 citation statements)

References 44 publications

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“…In this context, due to the effective combination of excellent intrinsic optoelectronic properties [ 6 ] with a unique solubility in green solvents, water/alcohol-soluble conjugated polymers (WSCPs) have attracted growing attention in recent years [ 7 , 8 , 9 , 10 ]. Water solubility of π-conjugated polymers, in particular poly(3-alkylthiophene)s, can be achieved and tailored by incorporating hydrophilic ionic moieties—such as imidazolium [ 11 , 12 ], amino [ 13 ], or phosphine groups [ 14 ]—to monomer and/or polymer side chains to obtain conjugated polyelectrolytes (CPEs).…”

Section: Introductionmentioning

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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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: Introductionmentioning

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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“…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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“…Recent papers have reported that regioregular head-to-tail CPTs are accessed via a two step approach: First, Ni-initiated polymerization to form regioregular poly[3-(6-bromoalkyl)thiophene-2,5-diyl] ,,,,,− or polymerization of a thiophene with ester pendant group by GRIM, followed by postpolymerization functionalization to install the cationic moiety (Scheme A; see Scheme , Table , and Schemes –). Zhang showed that GRIM method was not suitable for thiophenes bearing charged ionic side groups, so Kumada catalyst transfer polycondensation (KCTP) was performed to prepare the PT precursor with the ester side group.…”

Section: Advances In the Structures Mechanism And Properties Of Polyt...mentioning

confidence: 99%

Molecular Design, Synthetic Strategies, and Applications of Cationic Polythiophenes

Carreon-Asok

2019

Chem. Rev.

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This review delves into the synthesis of cationic-functionalized oligothiophenes and polythiophenes, their properties, and their diverse applications from the year 2002 to 2019. Pristine polythiophene chains are hydrophobic and are not easily converted into a form that is useful for broad applications or for device fabrications. Functional modification of the polymer side chain especially with cationic pendant groups imparts favorable properties to the system, such as solubility in aqueous medium and affinity with anions and negatively charged species, alongside the extensive π conjugation that provides unique optoelectronic characteristics. This review provides a detailed account of the design and the different synthetic strategies to access cationic polythiophenes (CPTs) via chemical oxidation using iron(III) chloride (FeCl 3 ), via metal catalyzed and initiated polymerization, and via postpolymerization functionalization approaches. CPTs have been traditionally used in sensing and as a component in optoelectronic devices; the utility of these systems has been extended to biomedical applications, such as nonviral gene delivery, cell targeting and imaging, anticancer, antifungal, and bactericidal actions, and biofilm formation, and to use as a molecular probe. A summary and outlook are also presented, discussing the remaining challenges and the future direction for this field.

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Novel conjugated polyelectrolytes based on polythiophene bearing phosphonium side groups

Cited by 14 publications

References 44 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

Molecular Design, Synthetic Strategies, and Applications of Cationic Polythiophenes

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