Photorefractive properties of bifunctional N-arylated carbazole derivatives in a carbazole polymer host matrix

Schaerlaekens, Mark; Hendrickx, Eric; Hameurlaine, Ahmed; Dehaen, Wim; Persoons, André

doi:10.1016/s0301-0104(01)00708-x

Cited by 13 publications

(8 citation statements)

References 26 publications

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“…Notable is the significantly lower reduction potentials of 2 (280 mV difference for the first reduction) compared with those of a prototypal decaaryl adduct, i.e., 4- n butylphenyl adduct (−2.13 and −2.51 V), indicating that the carbazolyl group acts as an electron-withdrawing group rather than a donating group as expected for an ordinary p -nitrogen substituent. It is evident that the nonplanar conformation of the carbazolylphenyl group relative to the phenylene group attached to the fullerene core (as indicated in Scheme ) does not allow the p -nitrogen lone pair to be conjugated to the phenylene π-system …”

mentioning

confidence: 99%

Light Emission of [10]Cyclophenacene through Energy Transfer from Neighboring Carbazolylphenyl Dendrons

Zhang

Nakamura

2008

Org. Lett.

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A dendritic deca(carbazolylphenyl)[60]fullerene bearing a cyclic benzenoid core was synthesized. The photophysical studies indicated that intramolecular energy transfer and electron transfer took place from the linked carbazolylphenyl moieties to the core-cyclic benzenoid moiety. The fluorescence quantum yield of the deca-adduct was determined to be 0.21 in toluene. Rich photophysical functions and their dendritic structures suggest that the photoactive decaadducts will serve as luminescent scaffolds in materials application.

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confidence: 99%

Light Emission of [10]Cyclophenacene through Energy Transfer from Neighboring Carbazolylphenyl Dendrons

Zhang

Nakamura

2008

Org. Lett.

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“…As a result, rotation of the phenyl ring occurs around the C-N bond, leading to a non-planar conformation. 15 Also, it has been already confirmed that N-aryl substitution of carbazoles clearly increases the total electron density. 14 This might be the reason of the higher affinity of N-arylated oligocarbazoles towards Pb 2+ .…”

Section: Potentiometric Responses Of Oligocarbazole-containing Ises Tmentioning

confidence: 83%

“…14,15 However, the conformation of this complex is still to be explored. The results obtained by spectroscopic measurements correlate well with the potentiometric responses of the oligocarbazole membranes.…”

Section: Spectroscopic Measurementsmentioning

confidence: 99%

“…Carbazoles and oligocarbazoles are compounds whose syntheses, molecular and photorefractive properties, and also electrochemical behavior are still being studied. [13][14][15] In view of their unique optical and electrical properties, carbazole derivatives have found applications in polymer films for the construction of biosensors. [16][17][18] Considerable effort is currently invested in the improvement of the selectivity and detection limits of ISEs.…”

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confidence: 99%

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Oligocarbazoles as Ligands for Lead-selective Liquid Membrane Electrodes

et al. 2004

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Ionophore-based liquid-membrane ion-selective electrodes (ISEs), because of their versatility and low cost, are becoming widely used for many applications as electrochemical sensors. The selectivity of ISEs is governed by specific receptors, immobilized in an organic membrane, which are responsible for the molecular recognition of the analyte at the aqueous/organic interface. 1-3The strong need for the selective determination of Pb 2+ in environment monitoring, food technology and clinical analysis still stimulates research that seeks suitable ionophore designs which would allow one to improve the selectivity and detection limits.Several types of ionophores including thiacrown ethers, 4,5 methoxy-substituted arylenevinylene derivatives, 6,7 diazacrown ethers, 8 calixarene phosphine oxide, 9 macrocyclic amides, 10 oxamides, acyclic dithiocarbamates, 11,12 were used for detection of lead(II) ions. Here we report on a sensing system involving oligocarbazoles ( Fig. 1) that, to our knowledge, have been applied for the first time as Pb 2+ -selective ionophores in ISEs. Carbazoles and oligocarbazoles are compounds whose syntheses, molecular and photorefractive properties, and also electrochemical behavior are still being studied. [13][14][15] In view of their unique optical and electrical properties, carbazole derivatives have found applications in polymer films for the construction of biosensors. [16][17][18] Considerable effort is currently invested in the improvement of the selectivity and detection limits of ISEs. [19][20][21][22] The success within this research area and the possibilities of miniaturized sensors based on ion-selective liquid membranes 23-25 make potentiometric sensors a promising alternative for other analytical methods and justify the requirements to design new, selective ionophores. In this context, oligocarbazoles derivatives, studied as a new class of ionophores for potentiometric determination of lead ions in water samples, is the main objective of the research presented. Warmia and Mazury, Faculty of Environmental Sciences and Fisheries, Oczapowskiego 5, Olsztyn, Poland ***University of Leuven, Department of Chemistry, Celestijnenlaan 200F, 3001 Leuven, Belgium Oligocarbazoles have been applied as new ionophores in liquid membrane electrodes (ISEs) destined for lead(II) determination in water samples. The oligocarbazole-containing ISEs demonstrated a close-to-Nernstian potentiometric response towards Pb 2+ in the activity range 10 -7 -10 -2 M. The selectivity coefficients measured by the matched potential method (MPM) confirmed their good selectivity against common interfering mono-and doubly charged cations. The oligocarbazole-containing ISEs do not respond towards protons. Their applicability has been checked by performing the recovery test while using a sample of wastewater.

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“…Recrystallization from DMF yielded 16 g (86% in yield) of nitro compound 2 as yellow needles with mp = 236–237 °C (ref. 20: 234–235 °C) measured by DSC at 10 °C/min.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, photoluminescence, and electrochromism of polyamides containing (3,6‐di‐tert‐butylcarbazol‐9‐yl)triphenylamine units

Wang

Hsiao

Liou

et al. 2010

J. Polym. Sci. A Polym. Chem.

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A new carbazole-derived, triphenylamine (TPA)containing aromatic dicarboxylic acid monomer, 4,4 0 -dicarboxy-4 00 -(3,6-di-tert-butylcarbazol-9-yl)TPA, was synthesized, and it led to a series of electroactive aromatic polyamides with main-chain TPA and pendent 3,6-bis(tert-butyl)carbazole units by reacting it with various aromatic diamines via the phosphorylation polyamidation technique. The polyamides were amorphous with good solubility in many organic solvents and could be solution-cast into flexible and strong films. They showed high glass-transition temperatures (282-335 C) and high thermal stability (10% weight loss temperatures >480 C). The electroactive polymer films had well-defined and reversible redox couples with good cycle stability in acetonitrile solutions. The polymer films also exhibited fluorescent and multielectrochromic behaviors. The anodically electrochromic polyamide films had moderate coloration efficiency ($100 cm 2 /C) and high optical contrast ratio of transmittance change (D%T) up to 47% at 813 nm and 48% at 414 nm for the green coloring. After hundreds of cyclic switches, the polymer films still retained good redox and electrochromic activity. V C 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: [4775][4776][4777][4778][4779][4780][4781][4782][4783][4784][4785][4786][4787][4788][4789] 2010

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Photorefractive properties of bifunctional N-arylated carbazole derivatives in a carbazole polymer host matrix

Cited by 13 publications

References 26 publications

Light Emission of [10]Cyclophenacene through Energy Transfer from Neighboring Carbazolylphenyl Dendrons

Light Emission of [10]Cyclophenacene through Energy Transfer from Neighboring Carbazolylphenyl Dendrons

Oligocarbazoles as Ligands for Lead-selective Liquid Membrane Electrodes

Synthesis, photoluminescence, and electrochromism of polyamides containing (3,6‐di‐tert‐butylcarbazol‐9‐yl)triphenylamine units

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