Triphenylamine-based electroactive compounds: synthesis, properties and application to organic electronics

Rybakiewicz, Renata; Zagórska, Małgorzata; Proń, Adam

doi:10.1007/s11696-016-0097-0

Cited by 37 publications

(20 citation statements)

References 152 publications

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“…Compared to the high reactivity of the radical cation of TPA, described above, the insertion of terminal groups at the para position of each phenyl ring combined with the -extension of the arms favor the stabilization of the radical cation species, hence preventing any follow-up dimerization of electropolymerization reactions. Note that compound DA 3 -1 displays also an irreversible reduction peak at E pr 1 = −1.65 V. Since then, many other DA 3 push-pull molecules derived from TPA have been successfully used as donor materials in BHJ OSCs in the presence of [6,6]-phenyl-C71-butyric acid methyl ester (PC 71 BM) as acceptor material. 11,12 Scheme 2 shows representative examples.…”

Section: Star-shaped Da 3 Push-pull Moleculesmentioning

confidence: 99%

“…Triphenylamine (TPA) derivatives are a class of versatile redox-active molecules that have attracted particular attention in relation to their promising hole transport properties. [1][2][3][4] Applications include various thin layer opto-electronic devices 1,5,6 comprising organic light emitting diodes (OLEDs), 7,8 electrochromic devices, 9 dye sensitized solar cells, organic solar cells (OSCs) [10][11][12] and perovskite solar cells. [12][13][14] The electron-rich character of TPA has also been exploited for electrochemical storage of energy 15 and electrical memory devices.…”

Section: Introductionmentioning

confidence: 99%

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

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

109

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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: Star-shaped Da 3 Push-pull Moleculesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

109

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“…However, it normally induced an additional peak at 2.2–2.3 eV (539–564 nm) for PF [26]. More importantly, TPA is electroactive where it can be excited by high applied voltage [27]. A TPA electromer or excited-state complex could be formed between molecules or subunits carrying a charge [22].…”

Section: Resultsmentioning

confidence: 99%

Photophysical and Electroluminescence Characteristics of Polyfluorene Derivatives with Triphenylamine

et al. 2019

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In this work, polymers of poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-triphenylamine] with side chains containing: pyrene (C1), diphenyl (C2), naphthalene (C3), and isopropyl (C6) structures were synthesized via a Suzuki coupling reaction. The structures were verified using NMR and cyclic voltammetry measurements provide the HOMO and LUMO of the polymers. The polymer with pyrene (C1) and naphthalene (C3) produced photoluminescence in the green while the polymer with the side chain containing diphenyl (C2) and isopropyl (C6) produce dual emission peaks of blue-green photoluminescence (PL). In order to examine the electroluminescence properties of the polymers, the solutions were spin-coated onto patterned ITO anode, dried, and subsequently coated with an Al cathode layer to form pristine single layer polymer LEDs. The results are compared to a standard PFO sample. The electroluminescence spectra resemble the PL spectra for C1 and C3. The devices of C2, C3, and C6 exhibit voltage-dependent EL. An additional red emission peak was detected for C2 and C6, resulting in spectra with peaks at 435 nm, 490 nm, and 625 nm. The effects of the side chains on the spectral characteristics of the polymer are discussed.

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“…In fact, triphenylamine is at the basis of numerous compounds developed for photovoltaic applications due to its remarkable charge transport ability and its low oxidation potential. [28][29][30][31][32][33][34][35][36] The chemical structures of the different triphenylamine-based dyes 9-11 synthesized by click chemistry are presented in Fig. 2.…”

Section: Push-pull Molecules and Light Responsive Organic Molecules Cmentioning

confidence: 99%

“…From a synthetic point of view, the first series (19)(20)(21)(22)(23)(24)(25)(26)(27) was prepared while using the azide group attached to the electrondonating moiety (34)(35)(36). The click reaction carried out under microwave irradiation could provide the different dyes with reaction yields ranging from 54 to 91% upon irradiating the solutions for 30-60 minutes.…”

Section: Push-pull Molecules and Light Responsive Organic Molecules Cmentioning

confidence: 99%

Recent advances in organic dyes and fluorophores comprising a 1,2,3-triazole moiety

Brunel

Dumur

2020

New J. Chem.

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Triphenylamine-based electroactive compounds: synthesis, properties and application to organic electronics

Cited by 37 publications

References 152 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

Photophysical and Electroluminescence Characteristics of Polyfluorene Derivatives with Triphenylamine

Recent advances in organic dyes and fluorophores comprising a 1,2,3-triazole moiety

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