Electrochemical formation of polycarbazole films in air- and water-stable room-temperature ionic liquids

Zhuang, Ding-Xuan; Chen, Po‐Yu

doi:10.1016/j.jelechem.2008.12.012

Cited by 22 publications

(20 citation statements)

References 30 publications

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“…The mechanism described here appears many times in t h e l i t e r a t u r e i n d e s c r i p t i o n s o f c a r b a z o l e electropolymerization or the process of polymer crosslinking via dicarbazole bridging [10][11][12][13][14][15][16].…”

Section: Electrochemical Oxidation Of Carbazolesmentioning

confidence: 99%

Carbazole electrochemistry: a short review

Karoń

Łapkowski

2015

J Solid State Electrochem

236

168

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Carbazole and its derivatives have become important materials for optoelectronic applications in recent years. In this work, we have collated information on the oxidation of carbazole and its derivatives. Knowledge of their electrochemical properties affords insight into the mechanisms for their oxidation and reduction as well as possible subsequent reactions. This knowledge therefore provides the basis for evaluating the stabilities of these materials and for designing novel carbazole-derived materials with desired properties as well as new devices.

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Section: Electrochemical Oxidation Of Carbazolesmentioning

confidence: 99%

Carbazole electrochemistry: a short review

Karoń

Łapkowski

2015

J Solid State Electrochem

236

168

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“…The oxidation of carbazole is rather complex and has the characteristics of an electrochemical-chemical-electrochemical (ECE) process in which one electron is involved per parent molecule. Interestingly, the carbazole amine derivatives show a slightly different nature of oxidation processes 32 . The presence of additional nitrogen atoms supplying electrons in the molecule reduces the initial oxidation potential compared to carbazole 33 .…”

Section: Resultsmentioning

confidence: 99%

“…For unsubstituted carbazoles, the 3, 6, and 9 positions are readily available as coupling sites. Substitution of the molecule in 3 and 6 positions eliminates their participation in the dimerization process, and thus the only likely coupling sites remain the 9(N) and optionally positions 1 or 8, respectively 30 – 32 . The type of dimer formed during oxidation depends on proton concentration in the area around the electrode, the status of the carbazole nitrogen (protonated or unprotonated), and the electron densities at the remaining reactive coupling sites 33 , 34 .…”

Section: Resultsmentioning

confidence: 99%

Photosensitive and pH-dependent activity of pyrazine-functionalized carbazole derivative as promising antifungal and imaging agent

Chylewska

Dąbrowska

Ramotowska

et al. 2020

Sci Rep

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Carbazole skeleton plays a significant role as a structural scaffold of many pharmacologically active compounds. Pyrazine-functionalized carbazole derivative was constructed by coupling 2-amino-5-bromo-3-methylaminepyrazine (ABMAP) into 3 and 6 positions of the carbazole ring. Multiexperimental methods were used, e.g., potentiometric, spectroscopic (ATR, UV, XRD powder, 1 H and 13 C NMR), electrochemical (cyclic voltammetry), and optical techniques, to receive the complete structural analysis, physicochemical (pKa, logP) and biological profile of a new carbazole derivative with acronym 3,6-PIRAMICAR. the interaction ability of the compound studied with potential cellular targets like Calf Thymus DNA (CT-DNA), or BovineSerumAlbumin (BSA) were also taken into account. experiments showed the existence of strong binding, but no DnA or BSA cleavage was observed. the comparative analyzes of compounds anti-Candida action clearly show pH-dependent antifungal activity of 3,6-PIRAMICAR , which was strongly stimulated in the acidic media. Surprisingly, the titled compound turn out to be much more effective (14 times by MIC50; 8 times by MIC; c.a. 4 times by MFC) against Candidakrusei than fluconazole at pH 4. The emergence of multidrug-resistant microorganisms, as well as fungal infectious diseases, is a major global problem, especially for immuno-deficient populations. The development of new antifungal agents in clinical trials is problematic inferior to the incidence of drug resistance, and the available antifungal agents are restricted. Their mechanisms are based on certain characteristics of the fungus in order to avoid biological similarities with the host 1. Fungi in the Candida genus are the most common fungal pathogens which can colonize various host niches (stomach, vagina and oral mucosa) with varying ambient pH range 2-6. Carbazoles and derivatives with carbazole skeleton are currently tested intensively according to their antimicrobial properties which is directly relating with their structure or in more details with anaromatic N-heterocyclic ring inside 7. Carbazole derivatives have been reported to be potential agents against tumor 8 or opportunistic infections of AIDS 9,10. The studies about high active DNA intercalators show the significance of the carbazole structural agents like planarity or aromaticity 11,12. Interestingly, the mentioned parameters are described as responsible for the high affinity of carbazoles substituted at 3,6-or 2,7-positions by amine, amidine, or imidazoline groups to GC or AT-rich sequences of DNA 13,14. However, chemistry of especially di-substituted 3,6-derivatives of carbazole is still not very extensively explored due to problems with synthesis of such compounds. Mainly nitrogen atom was a hot spot for carbazole derivatives 14. The first concept of the studies was to check the basic design structures assumptions to predict pharmaceuticals activity, like presented carbazole functionalized by pyrazines-our previous research objects. Consequently, the confirmation of the possibili...

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“…The fact that conjugated polymers can repeatedly undergo electrochemical doping/undoping processes makes them a promising class of material to be used in EC devices with wide hue of colors. These p-conjugated polymers offer support for the incorporation of ionic liquids into a variety of electrochemical materials and their reversible doping/ undoping processes make them suitable for application in electrochromic devices [21][22][23][24][25][26]. In contrast, PPy has received much less attention than polyaniline and poly(3,4-ethylenedioxythiophene) and other conjugated polymers due to the poor EC properties and a, b coupling [27].…”

Section: Introductionmentioning

confidence: 99%

Growth of N-substituted polypyrrole layers in ionic liquids: Synthesis and its electrochromic properties

Ahmad

Gürsoy

Kazim

et al. 2012

Solar Energy Materials and Solar Cells

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A new series of pyrrole family, N-substituted phenyl attached alkyl at the ortho, meta and para position were synthesized by a straight forward method and were exploited as an innovative monomer for electroactive polymers. Ionic liquids were employed as a medium for electro-polymerization of these monomers to obtain N-(methyl)phenyl polypyrroles. N-substituted polypyrroles show different morphologies and conductivity according to position of methyl group on the benzene ring and synthesis medium. The electrical conductivity value varies with the position of methyl group and was 410 À 5 S/cm, higher than the sample obtained from conventional media. The resulting polymer films were characterized by FT-IR and UV-Vis spectroscopy, contact angle measurements, cyclic voltammetry and scanning probe microscopic technique along with their electrochromic behavior.

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Electrochemical formation of polycarbazole films in air- and water-stable room-temperature ionic liquids

Cited by 22 publications

References 30 publications

Carbazole electrochemistry: a short review

Carbazole electrochemistry: a short review

Photosensitive and pH-dependent activity of pyrazine-functionalized carbazole derivative as promising antifungal and imaging agent

Growth of N-substituted polypyrrole layers in ionic liquids: Synthesis and its electrochromic properties

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