The anodic oxidation and polymerization of carbazoles and dicarbazoles N-substituted by polyether chains

Marrec, Philippe; Dano, Cécile; Gueguen-Simonet, Noëlle; Simonet, Jacques

doi:10.1016/s0379-6779(97)81214-3

Cited by 65 publications

(54 citation statements)

References 19 publications

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“…This is consistent with results reported in the literature for the electrochemical behavior of carbazole and its derivatives. [55,56] The oxidation peaks at relatively high potentials of 1.04 and 1.08 V are attributed to oxidation of the trimer fluorene units in the backbone of the compounds. [57,58] The oxidation-onset potentials for these compounds (0.79 V for TCPC-6 and 0.81 V for TCPC-4) are significantly lower than that for Mod I (1.01 V).…”

Section: Electrochemical Propertiesmentioning

confidence: 99%

“…In subsequent scans in the potential range from 1.15 to 0 V, reduction peaks are observed at 0.51 V for TCPC-6 and 0.49 V for TCPC-4, which correspond to the formation of neutral dimeric carbazyl from dimeric carbazyl cations. [55,56] The first CV scans of TCPC-6 and TCPC-4 show only a slight difference, indicating that the electrochemical properties of the compounds are not significantly influenced by the length of the peripheral alkyl chain.…”

Section: Full Papermentioning

confidence: 99%

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A Molecular Glass for Deep‐Blue Organic Light‐Emitting Diodes Comprising a 9,9′‐Spirobifluorene Core and Peripheral Carbazole Groups

Tang

Liu

Lü

et al. 2007

Adv Funct Materials

178

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Novel fluorene‐based compounds, TCPC‐6 and TCPC‐4, with rigid central spirobifluorene cores and peripheral carbazole groups are synthesized using the Suzuki coupling reaction. The optical, electrochemical, and thermal properties of these compounds are characterized. The compounds show strong deep‐blue emission both in solution and as thin films. Both TCPC‐6 and TCPC‐4 exhibit amorphous morphologies in the solid state with high glass transition temperatures (Tg) of 108 and 143 °C, respectively. Atomic force microscopy (AFM) measurements indicate that high‐quality amorphous films of these novel compounds can be prepared by spin‐coating. The oxidation potentials of TCPC‐6 and TCPC‐4 are significant lower than that of model compounds without peripheral carbazole groups, which suggests that these compounds have relatively high highest occupied molecular orbital (HOMO) energy levels and better hole‐injection capabilities. Light‐emitting devices fabricated by spin‐coating films of these molecules exhibit deep‐blue emission with Commission Internationale de l'Eclairage (CIE) chromaticity coordinates (x, y) of (0.16, 0.05); the devices fabricated using spin‐coated TCPC‐6 and TCPC‐4 layers exhibit high luminance efficiencies of 1.35 and 0.90 cd A–1 (with external quantum efficiencies of 3.72 and 2.47 %), respectively.

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Section: Electrochemical Propertiesmentioning

confidence: 99%

Section: Full Papermentioning

confidence: 99%

A Molecular Glass for Deep‐Blue Organic Light‐Emitting Diodes Comprising a 9,9′‐Spirobifluorene Core and Peripheral Carbazole Groups

Tang

Liu

Lü

et al. 2007

Adv Funct Materials

178

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show abstract

“…Previously reported ED films generally exhibited very poor device performance [19][20][21][22]. This is due to a variety of factors, such as structural defects, rough morphology, and strong fluorescence quenching from the doped counter ions present in the ED films [23][24][25]. To enhance the emissive efficiency of ED films, our group [26,27] designed and synthesized an electroactive and structurally well-defined compound TCPC (Fig.…”

Section: Introductionmentioning

confidence: 99%

Almost completely dedoped electrochemically deposited luminescent films exhibiting excellent LED performance

Tang

Yang

et al. 2009

Electrochimica Acta

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“…In general, electropolymerized conjugated polymers exhibit weak or no fluorescence, probably due to structural defects and quenching by doping counterions in the film [291,292]. Advincula and co-workers reported a luminescent thin film of conjugated polymer with pendant N-alkyl carbazole.…”

Section: Applications Of Carbazole Electrocoupling and Ec-lblmentioning

confidence: 99%

Electrochemical nanoarchitectonics and layer-by-layer assembly: From basics to future

et al. 2015

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No. of Pages 30 2 G. Rydzek et al. SummaryDuring the last few decades, electrochemistry and electrode modification have seen a tremendous fall off in creativity with the emergence of the nanoarchitectonic-based layerby-layer (LbL) film deposition technique. An unprecedented variety of building blocks can be immobilized on surfaces, leading to progress in several fields including sensing, electrochromic, electro-responsive and energy devices. This review describes the state of the art of electrochemical devices based on LbL assemblies, with a focus on supercapacitors, biosensors, and electroresponsive LbL such as electrodissolution/electroswelling of coatings. Recently, electrochemistry has also been used as an ''active trigger'' to induce the formation of films by covalent coupling, leading to new nanoarchitectonic approaches beyond the LbL strategy. These emerging electro-coupling reactions, including electroclick and carbazole chemistry, open new perspectives toward architecture and patterning of functional films and are extensively reviewed.

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The anodic oxidation and polymerization of carbazoles and dicarbazoles N-substituted by polyether chains

Cited by 65 publications

References 19 publications

A Molecular Glass for Deep‐Blue Organic Light‐Emitting Diodes Comprising a 9,9′‐Spirobifluorene Core and Peripheral Carbazole Groups

A Molecular Glass for Deep‐Blue Organic Light‐Emitting Diodes Comprising a 9,9′‐Spirobifluorene Core and Peripheral Carbazole Groups

Almost completely dedoped electrochemically deposited luminescent films exhibiting excellent LED performance

Electrochemical nanoarchitectonics and layer-by-layer assembly: From basics to future

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