Effect of π-conjugation on electrochemical properties of poly(terthiophene)s 3′-substituted with fullerene C 60

Czichy, Małgorzata; Wagner, Paweł; Łapkowski, Mieczysław; Officer, David L.

doi:10.1016/j.jelechem.2016.04.009

Cited by 10 publications

(9 citation statements)

References 44 publications

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“…The quasi-reversible redox couples recorded at lower potentials, i.e. at -0.7 and -0.9 V, comes from the reduction of C60 nanostructures incorporated in the organic matrix to form C60 •and C60 2-, respectively, and are in agreement with the signals recorded for fullerene solution with bare ITO electrode [33,34].…”

Section: Cyclic Voltammetrysupporting

confidence: 84%

Formation of poly(Azure A)-C60 photoactive layer as a novel approach in the heterogeneous photogeneration of singlet oxygen

Blacha–Grzechnik

Piwowar

Zdyb

et al. 2018

Applied Surface Science

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Fullerene, C60 photosensitizer was incorporated into poly(Azure A) in the process of electrochemical polymerization from the solution of corresponding dye and fullerene. The synthesized organic layer (PAA_C60/ITO) was characterized by means of cyclic voltammetry, UV-Vis, Raman and X-ray photoelectron spectroscopies. It was shown that PAA_C60/ITO exhibits strong absorption in both UV and Vis regions and that both immobilized photosensitizers, i.e. Azure A and C60, retain their photochemical activity towards 1 O2 generation under illumination as tested with 2,3,4,5-tetraphenylcyclopentadienone (TPCPD) singlet oxygen quencher. The electrodeposited photoactive layer composed of two photosensitizers was investigated as a source of 1 O2 in the process of α-terpinene oxidation.

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Section: Cyclic Voltammetrysupporting

confidence: 84%

Formation of poly(Azure A)-C60 photoactive layer as a novel approach in the heterogeneous photogeneration of singlet oxygen

Blacha–Grzechnik

Piwowar

Zdyb

et al. 2018

Applied Surface Science

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“…With macromers P3HT-(CH 2 ) 3 -MIM and P3HT-(CH 2 ) 3 -VIM in hand, we envisioned that they could be conveniently converted into linked P3HT-C 60 donor-acceptor dyads ( Scheme 2 ), an interesting topic of current investigations into photoinduced intramolecular energy transfer and electron transfer within such systems [ 32 , 33 , 34 , 35 , 36 , 47 ]. The proposed two-step procedure to construct such dyads, P3HT-(CH 2 ) 3 -MIM-C 60 and P3HT-(CH 2 ) 3 -VIM-C 60 , first involves deprotonation of the imidazolium chain end to generate the corresponding NHC moiety, followed by facile adduct formation between the polymeric NHC LB and all carbon LA C 60 , a method we established previously for the construction of poly(NHC-C 60 ) [ 41 ].…”

Section: Resultsmentioning

confidence: 99%

Brush Polymer of Donor-Accepter Dyads via Adduct Formation between Lewis Base Polymer Donor and All Carbon Lewis Acid Acceptor

et al. 2017

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A synthetic method that taps into the facile Lewis base (LB)→Lewis acid (LA) adduct forming reaction between the semiconducting polymeric LB and all carbon LA C60 for the construction of covalently linked donor-acceptor dyads and brush polymer of dyads is reported. The polymeric LB is built on poly(3-hexylthiophene) (P3HT) macromers containing either an alkyl or vinyl imidazolium end group that can be readily converted into the N-heterocyclic carbene (NHC) LB site, while the brush polymer architecture is conveniently constructed via radical polymerization of the macromer P3HT with the vinyl imidazolium chain end. Simply mixing of such donor polymeric LB with C60 rapidly creates linked P3HT-C60 dyads and brush polymer of dyads in which C60 is covalently linked to the NHC junction connecting the vinyl polymer main chain and the brush P3HT side chains. Thermal behaviors, electronic absorption and emission properties of the resulting P3HT-C60 dyads and brush polymer of dyads have been investigated. The results show that a change of the topology of the P3HT-C60 dyad from linear to brush architecture enhances the crystallinity and Tm of the P3HT domain and, along with other findings, they indicate that the brush polymer architecture of donor-acceptor domains provides a promising approach to improve performances of polymer-based solar cells.

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“…In the literature, many studies are devoted to examining the formation of polymeric materials based on polythiophenes or polythiophene derivatives and fullerenes or fullerene derivatives. [43][44][45][46][139][140][141][142][143][144][145][146][147][148][149][150][151][152] Because the oligo-and polythiophenes possess advantageous electronic properties, these materials show promise for use in applications mainly in organic electronics [45,138,139,147,148] and photoelectronics. [43,44,46,137,[141][142][143][144][145][146][147] In these "double cable" systems, the polythiophene backbone and fullerene pedant moiety independently retain their ground state properties.…”

Section: Polythiophene-based Side-chain C 60 Polymersmentioning

confidence: 99%

“…[43–46,139–152] Because the oligo‐ and polythiophenes possess advantageous electronic properties, these materials show promise for use in applications mainly in organic electronics [ 45,138,139,147,148 ] and photoelectronics. [ 43,44,46,137,141–147 ] In these “double cable” systems, the polythiophene backbone and fullerene pedant moiety independently retain their ground state properties. These materials are formed using different synthesis techniques.…”

Section: Polymers Containing Fullerene Moieties Covalently Linked To mentioning

confidence: 99%

“…[ 7,8,29,40–42 ] A large group of fullerene‐based materials consists of organic conducting polymers containing fullerenes attached covalently to the polymer chain by the linker. [ 43–46 ] The physicochemical properties of these materials depend on the polymer chain, linker structures, and the density of fullerene moieties within the polymeric material. Similar to olefins, fullerene form homopolymers through [2+2] cycloaddition.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Fullerene‐Based Conducting Polymers:n‐Dopable Materials for Charge Storage Application

Grądzka

Wysocka‐Żołopa

Winkler

2020

Advanced Energy Materials

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structure, which can be easily covalently modified. Progress in extensive organic chemistry of fullerene development facilitates the production of a variety of fullerene derivatives with different structures and physicochemical properties. Additionally, the polyhedral structure of fullerenes containing a large number of bonding sites provides an opportunity for a wide range of covalent modifications. Polymeric structures containing fullerene moieties represent a particularly large class of materials in terms of their number, composition, structure, morphology, and physicochemical properties. [24-29] Some of the most common structures of these polymeric materials are schematically shown in Figure 1. The simplest and most common structures are composites formed from the polymeric chains and fullerenes. Fullerenes form a crystalline phase in the polymeric matrix [30] or are incorporated as guest molecules into polymeric chain containing host moieties. [31] In both cases, covalent interactions are not formed between fullerenes and the polymeric network. However, van der Waals and electrostatic interactions, as well as possible charge transfer between both components of the composite significantly modulate the electronic structure of the polymer/fullerene interphase. [32,33] A stronger electronic interaction between the polymer component and fullerene moieties is expected for the system in which carbon cages are covalently bound to the polymeric chain or covalently incorporated into the polymeric backbone. In the case of in-chain structures, fullerene moieties are separated by short organic conjugated linkers, [34-37] small inorganic linkers, [37-39] or metal atoms and metal complexes. [7,8,29,40-42] A large group of fullerene-based materials consists of organic conducting polymers containing fullerenes attached covalently to the polymer chain by the linker. [43-46] The physicochemical properties of these materials depend on the polymer chain, linker structures, and the density of fullerene moieties within the polymeric material. Similar to olefins, fullerene form homopolymers through [2+2] cycloaddition. [47-51] Fullerene homopolymers, in-chain and side chain fullerene polymers can be cross-linked to form 3D polymeric structures. A large number of reactive π-bond centers in the fullerene moiety enable the formation of star-shaped macromolecular systems with polymeric chains covalently grafted to the C 60. [52-57] In common structures, the number of linked This article provides a comprehensive review of research related to the formation and electrochemical properties of fullerene-based conducting polymeric materials. The paper begins with an overview of composites containing fullerenes incorporated into the network of a conducting polymer through van der Walls, electrostatic, or guest-host interactions. The properties of these composites are generally a superposition of the properties of the individual components. More attention is devoted to the structures in which fullerene is covalently incorporated into the polyme...

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Effect of π-conjugation on electrochemical properties of poly(terthiophene)s 3′-substituted with fullerene C 60

Cited by 10 publications

References 44 publications

Formation of poly(Azure A)-C60 photoactive layer as a novel approach in the heterogeneous photogeneration of singlet oxygen

Formation of poly(Azure A)-C60 photoactive layer as a novel approach in the heterogeneous photogeneration of singlet oxygen

Brush Polymer of Donor-Accepter Dyads via Adduct Formation between Lewis Base Polymer Donor and All Carbon Lewis Acid Acceptor

Fullerene‐Based Conducting Polymers:n‐Dopable Materials for Charge Storage Application

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