Simultaneous doping and crosslinking of polythiophene films

Reinold, P.; Bruchlos, Kirsten; Ludwigs, Sabine

doi:10.1039/c7py01688c

Cited by 20 publications

(17 citation statements)

References 71 publications

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“…The second polymer, namely PT‐TPA, is composed of a linear regioregular polythiophene (PT) backbone bearing TPA redox pendants connected to the main backbone via click chemistry (Fig. ).…”

Section: Crosslinking In Polymer Films For Stable Redox‐active Filmssupporting

confidence: 87%

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

107

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This review article gives an overview of past and current activities in the Linear Conjugated Systems Group of Angers and in the IPOC – Functional Polymers Group of the Institute of Polymer Chemistry of Stuttgart on the use of triphenylamine (TPA) as versatile building block for organic electronics. In the first part, the properties of TPA itself are introduced including geometrical and energy level considerations. Dimerization of TPA to tetraphenylbenzidine upon electrochemical oxidation is highlighted. The blocking of TPA para‐positions and its implications in terms of electroactivity is further discussed. The second part shows that dimerization of TPA as pendant redox‐active moieties in polymers is a versatile strategy to crosslink polymer films. Coming from redox homopolymers the crosslinking strategy is extended towards conjugated redox polymers based on polythiophenes and block copolymers. Conductivity mechanisms and the influence of doping level on conductivity are probed with cyclic voltammetry coupled with in situ conductance and four‐point probe measurements. The last part is dedicated to the use of TPA as an electron‐donating block in the design of donor‐π‐acceptor chromophores and their use as active material in organic photovoltaics. An overview of some relevant TPA‐based push–pull molecules from the literature and our contribution to this field is presented emphasizing the progress of the photovoltaic performance of organic solar cells made over the last decade. © 2018 Society of Chemical Industry

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Section: Crosslinking In Polymer Films For Stable Redox‐active Filmssupporting

confidence: 87%

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

107

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“…The response is characterized by a sigmoidal transition from a neutral (non‐conducting) to an oxidized or reduced state (conducting) in a G vs E plot, which can be correlated with the corresponding voltammogram. (Figure ) . These curves can be depicted in two formats; linear or logarithmic scale for the conductance values.…”

Section: Chemical Aspects Related To In Situ Electrochemical‐conductamentioning

confidence: 99%

“…(Figure 8). [79,84,116,117] These curves can be depicted in two formats; linear or logarithmic scale for the conductance values. In some cases, is important to analyze the semi-conducting region (10 À 4 � σ � 10 À 0 Ω À 1 cm À 1 ) in order to extract important information about the electrical material behavior.…”

Section: Studies On Conductivity Models Based On the In Situ Electrocmentioning

confidence: 99%

“…The conductivity profile during the charge process of πconjugated polymers by means of the in situ electrochemicalconductivity experiments is characterized, as mentioned pre- viously, by a sigmoidal increase of the conductivity followed by a plateau where, in some examples, no further changes are observed. [79,83,117] In the course of the discharge process the conductivity begins to decrease in a similar way, however, usually both processes occur at different potentials values. [133] This phenomenon is known as hysteresis and is very common during different in-situ techniques (Figure 10, ΔE G ).…”

Section: Studies Of the Charge/discharge Process In Conducting Polymementioning

confidence: 99%

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Analysis of Conjugated Polymers Conductivity by in situ Electrochemical‐Conductance Method

Salinas

Frontana‐Uribe

2019

ChemElectroChem

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The in situ electrochemical‐conductance method is presented as an important electrochemical characterization tool for gaining insight into the chemical and electrical behavior of π‐conjugated polymers and electroactive materials. Important information about conductivity models, the type of charge carrier, and the carrier‐transport pathways as well as explanations of different phenomena related to charge and mass transport can be extracted from the obtained analyses. Using conveniently modified polymers, this method enables the development of a wide range of conductometric sensory devices. This Minireview summarizes the historical development of the in situ electrochemical‐conductance method, describes the systems used, explains details of the calculations, and discusses recent advances and applications.

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“…Another attractive approach for the obtainment of functionalized triarylamine electroactive surface, as an alternative to electrodeposition from monomer solution, exploits the dimerizing ability of arylamine units just in a post deposition step of pre‐deposited films. In this case the triarylamine unit is present for example as a redox‐active pendant covalently bound to a polymer backbone, acting as a cross‐linker unit upon oxidative triggering, and generating polymer films crosslinked with redox‐active tetraphenylbenzidine (TPB) moieties …”

Section: Introductionmentioning

confidence: 99%

Impact of the Replacement of a Triphenylamine by a Diphenylmethylamine Unit on the Electrochemical Behavior of Pentaerythritol‐Based Push‐Pull Tetramers

et al. 2019

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The synthesis of a tetra‐functionalized pentaerythritol core decorated with N‐methyl‐N,N‐diphenylamine‐based push‐pull chromophores and its electropolymerization to 3D push‐pull networks are described. The electrochemical and absorption behaviors of the tetramer are compared with the one of two reference linear push‐pull compounds, carrying triphenylamine (TPA) or methyldiphenylamine (MeDPA) donor groups, a thienyl linker and a dicyanovinyl acceptor group (DCV). We found that substituting the outer phenyl with a methyl group causes important differences in the radical cation stability, such that MeDPA chromophore generates stable dimers and TPA is reversibly oxidized. Interestingly, DFT calculations suggest that steric hindrance and electrostatic interactions dominate the radical cation reactivity.

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Simultaneous doping and crosslinking of polythiophene films

Cited by 20 publications

References 71 publications

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Analysis of Conjugated Polymers Conductivity by in situ Electrochemical‐Conductance Method

Impact of the Replacement of a Triphenylamine by a Diphenylmethylamine Unit on the Electrochemical Behavior of Pentaerythritol‐Based Push‐Pull Tetramers

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