Carbazole electrochemistry: a short review

Karoń, Krzysztof; Łapkowski, Mieczysław

doi:10.1007/s10008-015-2973-x

Cited by 236 publications

(191 citation statements)

References 36 publications

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“…[45] The evolution of the CVs is even accentuated when cycling between 0.2 and 1.86 V( Figure 4C)w ith a complete disappearance of the first oxidation wave at 0.86 V, in favour of the appearance and the regular growth of an ew redox system centred at 1.5-1.3 V, and the covering of the electrode surface with an insoluble deposit. Although anodic coupling is aw ell-known technique to generate p-conjugated oligomers and polymers from various linear building blocks, [46,51,52] as far as we know, this strategy has never been used forn anorings. Although anodic coupling is aw ell-known technique to generate p-conjugated oligomers and polymers from various linear building blocks, [46,51,52] as far as we know, this strategy has never been used forn anorings.…”

Section: Resultsmentioning

confidence: 99%

“…Although anodic coupling is aw ell-known technique to generate p-conjugated oligomers and polymers from various linear building blocks, [46,51,52] as far as we know, this strategy has never been used forn anorings. [47][48][49][50][51][52][53] Firstly,t his particularity can be explained by the carbon atoms involved in the coupling.I ndeed, as previously shown with variousc arbazole oligomers or polymers, [46] such type of anodic couplings take place at the C3 and C6 carbon atoms (as forc lassical electrophilic aromatics ubstitutions), [54] which are both in meta position of the biphenyl linkagel eading to an electronic decoupling. The electrochemical behaviour of the electrodepositedm aterials tudied in as olutioni na bsence of any electroactives ubstance ( Figure 4D)s hows ar eversible redoxp rocess with am aximum at 1.5 Va nd E onset ox = 1.02 V( HOMO = À5.42 eV).…”

Section: Resultsmentioning

confidence: 99%

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[4]Cyclo‐N‐ethyl‐2,7‐carbazole: Synthesis, Structural, Electronic and Charge Transport Properties

Lucas

Sicard

Jeannin

et al. 2019

Chemistry A European J

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Nanorings, which are macrocyclesp ossessing radially directed p-orbitalsh ave shown fantastic developmenti n the last ten years. Unravelling their unusuale lectronicp roperties has been one of the driving forces of this research field. However,a nd despite promising properties, their incorporationi no rganic electronic devices remains very scarce. In this work, we aim to contribute to bridge the gap between organice lectronics and nanorings by reporting the synthesis, the structurala nd electronic properties and the incorporation in an organic field-effect transistor (OFET) of ac yclic tetracarbazole, namely[ 4]cyclo-N-ethyl-2,7-carbazole( [4]C-Et-Cbz). The structural, photophysicala nd electrochemical properties have been compared to those of structurally related analogues [4]cyclo-9,9-diethyl-2,7-fluorene [4]C-diEt-F (with carbon bridges) and [8]-cycloparaphenylene [8]CPP (withouta ny bridge) in ordert os hed light on the impact of the bridging in nanorings. This work shows that nanorings can be used as an active layer in an OFET and provides a first benchmark in term of OFET characteristicsf or this type of molecules.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

[4]Cyclo‐N‐ethyl‐2,7‐carbazole: Synthesis, Structural, Electronic and Charge Transport Properties

Lucas

Sicard

Jeannin

et al. 2019

Chemistry A European J

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“…This feature will prevent an oxidative polymerization typical for carbazole derivatives and hence stabilize the charged redox states of the molecules. 37 5. Addition of thiophene -based linkers results in almost complete quenching of emission what might be caused by the stronger push-pull effect for systems with elongated conjugation framework.…”

Section: Resultsmentioning

confidence: 99%

Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole–BODIPY donor–acceptor systems

et al. 2016

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(2016). Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole-BODIPY donor-acceptor systems. RSC Advances: an international journal to further the chemical sciences, 6 (43), 36500-36509.Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole-BODIPY donor-acceptor systems Abstract Synthesis, spectral and electrochemical properties of a series of new panchromatic BODIPY donor-acceptordonor derivatives, comprising carbazole conjugated with systematically elongated framework by thiophenebased linkers were investigated. It has been found that elongation of the π-system with one thiophene unit shifts the spectra toward near infrared, while incorporation of next thiophene derivatives has only limited influence on the lowest energy transition, causing no further shift of absorption maxima. Elongation of π-conjugation of the donor arm tunes the electron properties, influencing the ionization potential (IP) and electron affinity (EA) values of the molecules. The experimental results are supported by quantum chemical computations revealing that electron density of SOMO orbital is low at the 3-positions of terminal carbazole units in BODIPY push-pull oligomers while elongating their backbone, thus preventing them to undergo electrochemical polymerization giving reversibly p-and n-dopable products. Presented study tests the influence and limitations of incorporation of electron-rich substituents for designing panchromatic BODIPY systems. elongating their backbone, thus preventing them to undergo electrochemical polymerization giving reversibly p-and n-dopable products. Presented study tests the influence and limitations of incorporation of electron -rich substituents for designing panchromatic BODIPY systems.

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“…33 Indeed, Siove and co-workers showed that a monomer in which two carbazole units are tethered by an N-substituted alkyl spacer merely leads to sequential dimerization upon chemical oxidation to form a polymer that could be spin-cast on electrodes. 34 The C–C coupling para to the nitrogen upon (electro)oxidation 24−26 via a 4 electron ECCE process is analogous to the dimerization of indoline derivatives 35 and N , N -dialkyl substituted anilines, 36−38 which occur readily.…”

Section: Introductionmentioning

confidence: 99%

Reversible Charge Trapping in Bis-Carbazole-Diimide Redox Polymers with Complete Luminescence Quenching Enabling Nondestructive Read-Out by Resonance Raman Spectroscopy

et al. 2017

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The coupling of substituted carbazole compounds through carbon–carbon bond formation upon one-electron oxidation is shown to be a highly versatile approach to the formation of redox polymer films. Although the polymerization of single carbazole units has been proposed earlier, we show that by tethering pairs of carbazoles double sequential dimerization allows for facile formation of redox polymer films with fine control over film thickness. We show that the design of the monomers and in particular the bridging units is key to polymer formation, with the diaminobenzene motif proving advantageous, in terms of the matching to the redox potentials of the monomer and polymer film and thereby avoiding limitations in film thickness (autoinsulation), but introduces unacceptable instability due to the intrinsic redox activity of this moiety. The use of a diimide protecting group both avoids complications due to p-diamino-benzene redox chemistry and provides for a redox polymer in which the photoluminescence of the bis-carbazole moiety can be switched reversibly (on/off) with redox control. The monomer design approach is versatile enabling facile incorporation of additional functional units, such as naphthalene. Here we show that a multicomponent carbazole/naphthalene containing monomer (APCNDI) can form redox polymer films showing both p- and n- conductivity under ambient conditions and allows access to five distinct redox states, and a complex electrochromic response covering the whole of the UV/vis–NIR spectral region. The highly effective quenching of the photoluminescence of both components in poly-APCNDI enables detailed characterization of the redox polymer films. The poly-APCNDI films show extensive charge trapping, which can be read out spectroscopically in the case of films and is characterized as kinetic rather than chemical in origin on the basis of UV/vis–NIR absorption and resonance Raman spectroscopic analyses. The strong resonantly enhanced Raman scattering for the various oxidized and reduced states of APCNDI enables nondestructive “read-out” of the state of the polymer, including that in which charges are trapped kinetically at the surface, making poly-APCNDI highly suitable for application as a component in organic nonvolatile memory devices.

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Carbazole electrochemistry: a short review

Cited by 236 publications

References 36 publications

[4]Cyclo‐N‐ethyl‐2,7‐carbazole: Synthesis, Structural, Electronic and Charge Transport Properties

[4]Cyclo‐N‐ethyl‐2,7‐carbazole: Synthesis, Structural, Electronic and Charge Transport Properties

Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole–BODIPY donor–acceptor systems

Reversible Charge Trapping in Bis-Carbazole-Diimide Redox Polymers with Complete Luminescence Quenching Enabling Nondestructive Read-Out by Resonance Raman Spectroscopy

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