Carbazole derivative synthesis and their electropolymerization

Ateş, Murat; Uludag, Nesimi

doi:10.1007/s10008-016-3269-5

Cited by 35 publications

(17 citation statements)

References 148 publications

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“…In a similar way, some transformations currently seem very challenging via an electrochemical approach. Examples are the usage of carbazoles due to electropolymerization (Section 2.4) [84,88,89,90,91] and the difficulty of employing aldehydes as acyl radical precursors [3] compared to the photochemical approach [198].…”

Section: Discussionmentioning

confidence: 99%

“…Nonetheless, it is currently impossible to use substoichiometric amounts of mediator because the exposure of carbazoles to electrochemical conditions results in a complex reaction mixture. The electrolysis of carbazole and its derivatives is quite complex as anodic oxidation of carbazoles leads to homocoupling and electropolymerization [88,89,90]. This exhibits a flaw of this methodology as it uses stoichiometric amounts of chemical oxidants.…”

Section: Side By Side Comparison Of Synthetic Methodologiesmentioning

confidence: 99%

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Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis

2019

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This review provides an overview of synthetic transformations that have been performed by both electro- and photoredox catalysis. Both toolboxes are evaluated and compared in their ability to enable said transformations. Analogies and distinctions are formulated to obtain a better understanding in both research areas. This knowledge can be used to conceptualize new methodological strategies for either of both approaches starting from the other. It was attempted to extract key components that can be used as guidelines to refine, complement and innovate these two disciplines of organic synthesis.

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Section: Discussionmentioning

confidence: 99%

Section: Side By Side Comparison Of Synthetic Methodologiesmentioning

confidence: 99%

Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis

2019

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“…[25] It is also known that the particular photophysics of carbazole-containing polymers is responsible for its good electron donor capacity and outstanding photoelectrical properties. [26][27][28] Among carbazole derivatives N-phenyl-carbazoles are of particular interest due to display high thermal stabilities and tunable photoluminescence, which directly influences their optical and electric properties. [29,30] By attaching proper substituents the dihedral angle between N-phenyl ring and carbazole moiety can be modified, so affecting the grade of electron delocalization and the energy of the electronic excited states.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species

Ramírez

Mangione

Bertolotti

et al. 2018

Journal of Photochemistry and Photobiology A: Chemistry

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Highlights  Ground and singlet excited states of N-phenyl-carbazoles were characterized.  Properties of dicarbazoles are susceptible to electronic coupling between single units.  The oxidized species were analyzed by cyclic voltammetry and spectroelectrochemistry.  An electrochromic polymer was deposited by electropolymerization.  The studied compounds might be suitable as fluorescent sensors and hole transporters.

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“…Conjugated copolymers based on carbazole derivatives are materials that have generated increasing interest in the past years for organic electronics . But based on our knowledge there is a lack of works dealing with the functionalization of this polymer by a redox group such as TEMPO derivatives for electrochemical energy applications.…”

Section: Introductionmentioning

confidence: 99%

A New Conducting Copolymer Bearing Electro‐Active Nitroxide Groups as Organic Electrode Materials for Batteries

et al. 2020

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To reduce the amount of conducting additives generally required for polynitroxide‐based electrodes, a stable radical (TEMPO) is combined with a conductive copolymer backbone consisting of 2,7‐bisthiophene carbazole (2,7‐BTC), which is characterized by a high intrinsic electronic conductivity. This work deals with the synthesis of this new polymer functionalized by a redox nitroxide. Fine structural characterization using electron paramagnetic resonance (EPR) techniques established that: 1) the nitroxide radicals are properly attached to the radical chain (continuous wave EPR) and 2) the polymer chain has very rigid conformations leading to a set of well‐defined distances between first neighboring pairs of nitroxides (pulsed EPR). The redox group combined with the electroactive polymer showed not only a very high electrochemical reversibility but also a perfect match of redox potentials between the de‐/doping reaction of the bisthiophene carbazole backbone and the redox activity of the nitroxide radical. This new organic electrode shows a stable capacity (about 60 mAh g−1) and enables a strong reduction in the amount of carbon additive due to the conducting‐polymer skeleton.

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Carbazole derivative synthesis and their electropolymerization

Cited by 35 publications

References 148 publications

Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis

Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis

A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species

A New Conducting Copolymer Bearing Electro‐Active Nitroxide Groups as Organic Electrode Materials for Batteries

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