Electrochemical and Photophysical Properties of a Novel Polythiophene with Pendant Fulleropyrrolidine Moieties:  Toward “Double Cable” Polymers for Optoelectronic Devices

Cravino, Antonio; Zerza, G.; Neugebauer, Helmut; Maggini, Michele; Bucella, Stefania; Menna, Enzo; Svensson, Mattias; Andersson, Mats R.; Brabec, Christoph J.; Sariciftci, Niyazi Serdar

doi:10.1021/jp013077y

Cited by 85 publications

(75 citation statements)

References 46 publications

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“…Fullerene C 60 with covalently linked zinc meso-tetraphenylporphyrin, ZnPo-C 60 or ZnPp-C 60 , was synthesized according to a method described in the literature [39]. Palladium acetate, Pd(ac) 2 (Aldrich) and C 60 (Southern Chemical Group) were used as received.…”

Section: Methodsmentioning

confidence: 99%

Redox Active Two-Component Films of Palladium and Covalently Linked Zinc Porphyrin–Fullerene Dyad

et al. 2006

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Redox active films have been generated electrochemically by the reduction of dyads consisting of fullerene C 60 covalently linked to zinc meso-tetraphenyloporphyrin, ZnPÀC 60 , and palladium acetate. The films are believed to consist of a polymeric network formed via covalent bonds between the palladium atoms and the fullerene moieties. In these films, the zinc porphyrin moiety is covalently linked to the polymeric chains through the pyrrolidine ring of the fullerene. The ZnPÀC 60 /Pt films are electrochemically active in both positive and negative potential excursions. At positive potentials, two oxidation steps for the zinc porphyrin are observed. In the negative potential range, electron transfer processes involving the zinc porphyrin and the fullerene entities are observed. Film formation is also accompanied by palladium deposition on the electrode surface. The presence of a metallic phase in the film influences its morphology, structure and electrochemical properties.

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Section: Methodsmentioning

confidence: 99%

Redox Active Two-Component Films of Palladium and Covalently Linked Zinc Porphyrin–Fullerene Dyad

et al. 2006

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“…34,35 A solar cell made using a double cable compound with a hybrid poly(p-phenylene vinylene)/poly(p-phenylene ethynylene) backbone and attached methanofullerenes was first reported by Janssen and co-workers. 36 Singlet EET to the fullerene was found to occur in non-polar solution, while the polymer fluorescence was quenched by photoinduced CS in thin films, yielding charge carriers with a millisecond lifetime.…”

Section: Introductionmentioning

confidence: 99%

Ultrafast spectroscopic investigation of a fullerene poly(3-hexylthiophene) dyad

et al. 2011

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We present the femtosecond spectroscopic investigation of a covalently linked dyad, PCB-P3HT, formed by a segment of the conjugated polymer P3HT (regioregular poly(3-hexylthiophene) that is end-capped with the fullerene derivative PCB ([6,6]-phenyl-C 61 -butyric acid ester), adapted from PCBM. The fluorescence of the P3HT segment in tetrahydrofuran (THF) solution is reduced by 64% in the dyad compared to a control compound without attached fullerene (P3HT-OH). Fluorescence upconversion measurements reveal that the partial fluorescence quenching of PCB-P3HT in THF is multiphasic and occurs on an average time scale of 100 ps, in parallel to excited-state relaxation processes. Judging from ultrafast transient absorption experiments, the origin of the quenching is excitation energy transfer from the P3HT donor to the PCB acceptor. Due to the much higher solubility of P3HT compared to PCB in THF, the PCB-P3HT dyad molecules self-assemble into micelles. When pure C 60 is added to the solution, it is incorporated into the fullerene-rich center of the micelles. This dramatically increases the solubility of C 60 , but does not lead to significant additional quenching of the P3HT fluorescence by the C 60 contained in the micelles. In PCB-P3HT thin films drop-cast from THF, the micelle structure is conserved. In contrast to solution, quantitative and ultrafast (<150 fs) charge separation occurs in the solid-state films and leads to the formation of long-lived mobile charge carriers with characteristic transient absorption signatures similar to those that have been observed in P3HT:PCBM bulk heterojunction blends. While π-stacking interactions between neighboring P3HT chains are weak in the micelles, they are strong in thin films drop-cast from ortho-dichlorobenzene (DCB). Here, PCB-P3HT self-assembles into a network of long fibers, clearly seen in AFM images.Ultrafast charge separation occurs also for the fibrous morphology, but the transient absorption experiments show fast loss of part of the charge carriers due to intensity-induced 2 recombination/annihilation processes and monomolecular interfacial trap-mediated or geminate recombination. The yield of the long-lived charge carriers in the highly organized fibers is however comparable to that obtained with annealed P3HT:PCBM blends. PCB-P3HT can therefore be considered as an active material in organic photovoltaic devices.

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“…Unfortunately, no photoelectrochemical measurements were performed in order to probe PV properties in this study. Several investigations following a similar pattern of electrochemical characterization have also been reported concerning the electropolymerization of PTh precursors with pendant C 60 groups, namely, by the groups of Ferraris [62,63], Cravino [64][65][66][67], Komatsu [68,69], and Wallace [70,71]. Beyond the similar pattern of electrochemical measurements established in the first report by Sannicolo and coworkers, a limited number of more insightful investigations have been reported.…”

Section: Polythiophenes Via Electropolymerization Of Precursors Functmentioning

confidence: 68%

“…This approach avoids the problems associated with the simple blending of donors and acceptors, including phase separation and immiscibility of materials. Several examples of the electropolymerization of PTh precursors with covalently attached C 60 functionalities have been reported (Figure 11.3) [61][62][63][64][65][66][67][68][69][70][71]. The first such investigation was reported by Sannicolo and coworkers [61] for a cyclopentadithiophene-fullerene precursor ( Figure 11.3a), which was electropolymerized by CV.…”

Section: Polythiophenes Via Electropolymerization Of Precursors Functmentioning

confidence: 99%

“…measured I sc values of ∼1 µA cm −2 under 50 mW cm −2 white-light illumination in a half-cell employing a photoanode, based on the Structures of C 60 -functionalized PTh precursors utilized following electropolymerization as possible photoactive materials for energy conversion: (a) a cyclopentadithiophene-fullerene[61], (b) a 3 -alkyl-2,2 -bithienyl-fullerene[62,63], (c) a bithiophene-fulleropyrrolidine[64][65][66][67], (d) a terthiophene-fullerene dyad, R = −H or −CH 3…”

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confidence: 99%

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Inherently Conducting Polymers via Electropolymerization for Energy Conversion and Storage

Wallace

Tsekouras

Wang

2010

Electropolymerization

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Inherently conducting polymers (ICPs) have found widespread application as electrode materials for energy conversion and storage. The use of electropolymerization to produce such materials and structures containing them has a number of advantages including the fact that localized polymerization onto electrode structures ensures • the ability to incorporate a wide range of dopants • intimate electrical connection • spatial control • ease of fabrication of microstructures • careful control over the polymer oxidation state • the ability to form copolymers • sequential deposition to produce layered structures.In this chapter, we examine the use of electropolymerization to produce ICPs for use in solar cells (an example of energy conversion) and for polymer electrodes used in batteries and supercapacitors (energy storage). ICPs prepared via electrodeposition have also found use in catalytic electrodes for fuel cells; however, this application is not covered here.It has been widely accepted that the physicochemical and electrochemical properties of ICPs depend strongly on many factors encountered during electrodeposition [1]. These include electrochemical technique, working electrode substrate, and electrolyte [2][3][4][5]. The following considers each of these variables in turn, before the discussion is shifted to consider the application of ICPs in energy conversion and storage.

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Electrochemical and Photophysical Properties of a Novel Polythiophene with Pendant Fulleropyrrolidine Moieties: Toward “Double Cable” Polymers for Optoelectronic Devices

Cited by 85 publications

References 46 publications

Redox Active Two-Component Films of Palladium and Covalently Linked Zinc Porphyrin–Fullerene Dyad

Redox Active Two-Component Films of Palladium and Covalently Linked Zinc Porphyrin–Fullerene Dyad

Ultrafast spectroscopic investigation of a fullerene poly(3-hexylthiophene) dyad

Inherently Conducting Polymers via Electropolymerization for Energy Conversion and Storage

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