- A new route towards fluorescent organic nanoparticles with red-shifted emission and increased colloidal stability
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Suzuki-Miyaura cross-coupling reaction with a new boron reagent has been used to conveniently and efficiently synthetize a dipolar chromophore having an elongated π-conjugated system (i.e., bithiophene based), which displays a red-shifted emission while m
- Amro, Kassem,Daniel, Jonathan,Clermont, Guillaume,Bsaibess, Talia,Pucheault, Mathieu,Genin, Emilie,Vaultier, Michel,Blanchard-Desce, Mireille
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- Synthesis and photophysical properties of fluorescent dyes based on triphenylamine, diphenylamine, diphenyl sulfone or triphenyltriazine derivatives containing an acetylene linkage group
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In this study, ten fluorescent dyes were prepared based on three different kinds of central moiety, such as triphenylamine, diphenylsulfone or triphenyltriazine, which was coupled to either carbazole or naphthalimidinyl group via an acetylene linkage group. N-n-Butyl-carbazole, N-phenyl-carbazole or N-n-butyl-naphthalimide was coupled to the individual central moiety of triphenylamine, diphenyl sulfone, 2,4,6-triphenyl-1,3,5-trazine or diphenylamine using a Sonogashira coupling reaction in the final step. All dyes were confirmed their chemical structure by 1H NMR, GC-Mass and elemental analyses. The absorption properties and thermal stabilities of the fluorescent dyes were examined. Density Functional Theory (DFT) and Time-Dependent DFT calculations were carried out, in addition to geometry simulation, by using the Gaussian 09 program. In terms of fluorescence properties in this series, two dyes based on diphenyl sulfonyl and three dyes based on triphenylamine substituted by 1–3 of N-n-butyl-carbazole exhibited a blue emission, whereas three dyes based on triphenylamine substituted by 1–3 of N-n-butyl-naphthalimide were observed by a red emitter which can be attributable to both effects the bathochromic shifts in absorption maxima and larger Stokes shifts. In case of corresponding 2,4,6-triphenyl-1,3,5-trazine central moiety coupled to a carbazole ring, a green fluorescence was emitted. Results revealed that the fluorescence of the dyes is affected by the electron-donating strength of the acetylene linkages involved in the π-conjugation systems of the dyes.
- Ahn, Sung-Ok,Choi, Jae-Hong,Kim, Kyung-Won,Kwon, Su-Hyeon,Lee, Byung-Jun,Lee, Ju-Hong
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- ORGANIC LIGHT-EMITTING DIODE MATERIALS
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Described herin are molecules for use in organic light emitting diodes. Example molecules comprise at least one acceptor moiety A, at least one donor moiety D, and optionally one or more bridge moieties B. Each moiety A is covalently attached to either the moiety B or the moeity D, each moiety D is covalently attached to either the moeity B or the moeity A, and each B is covalently attached to at least one moiety A and at least one moiety D. Values and preferred values of moieties A, D and B are defined herein.
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Paragraph 0546
(2018/08/09)
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- Electron-Catalyzed Coupling of Magnesium Amides with Aryl Iodides
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An electron was found to catalyze the coupling of magnesium diarylamides with aryl iodides giving triarylamines through a radical-anion intermediate. The transformation requires no transition metal catalysts or additives, and a wide array of products are formed in good-to-excellent yields.
- Kiriyama, Kazuya,Okura, Keisho,Tamakuni, Fumiko,Shirakawa, Eiji
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supporting information
p. 4519 - 4522
(2018/03/13)
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- Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes
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Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable ipso-iododeboronation procedure that uses NIS in the non-toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter-expressing tumours.
- Webster, Stacey,O'Rourke, Kerry M.,Fletcher, Conor,Pimlott, Sally L.,Sutherland, Andrew,Lee, Ai-Lan
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supporting information
p. 937 - 943
(2017/12/26)
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- Multipodal arrangement of push-pull chromophores: a fundamental parameter affecting their electronic and optical properties
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A series of model push-pull molecules with linear, quadrupolar, and tripodal arrangements, a varyingly substituted amino donor, two acceptors, and a partially extended π-system has been prepared. Two peripheral electron acceptors, namely N,N′-dibutylbarbituric acid and dicyanovinyl, were employed. The fundamental properties of 24 push-pull chromophores were investigated by differential scanning calorimetry, electrochemistry, one-photon absorption spectroscopy, photoinduced piezooptics, and were supported by DFT calculations. Thorough structure-property relationships were elucidated, while a significant influence of the structural arrangement/branching on the electronic and optical properties has been revealed. The fundamental optoelectronic properties of push-pull molecules are affected by their arrangement (linear/quadrupolar/tripodal), the peripheral acceptor attached, extension and planarization of the π-system, and also by the type of auxiliary N-substituent.
- Klikar,Kityk,Kulwas,Mikysek,Pytela,Bure?
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supporting information
p. 1459 - 1472
(2017/02/23)
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- Remarkable Influence of Phenyl/Arylethynylation on the Photochromism of 2,2-Diphenylbenzopyrans (Chromenes)
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Phenyl/arylethynylation of 2,2-diphenylbenzopyrans (i.e., chromenes) permits modulation of the spectral properties of photogenerated colored o-quinonoid intermediates, and brings about remarkable stabilization of the latter, rendering the phenomenon of ph
- Mukhopadhyay, Arindam,Maka, Vijay Kumar,Moorthy, Jarugu Narasimha
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supporting information
p. 274 - 281
(2016/02/14)
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- Solvent and branching effect on the two-photon absorption properties of push-pull triphenylamine derivatives
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The photophysical and two-photon absorption (2PA) properties of two tri-podal molecules and of their quadrupolar and dipolar counterparts are reported for a series of solvents with varying polarity. The molecules possess a tri-phenylamine electron donating group and mono-cyano acceptors while olefinic and acetylenic π-linkers have been used. Branching led to an increase of the molar extinction coefficient and to a slight bathochromic shift of the absorption spectra while the fluorescence quantum yields decrease but they are maintained to relatively high values. Solvatochromic measurements in the tri-podal molecules revealed an emitting state with a polar nature. The 2PA cross sections in general increase upon branching but the observed behaviour strongly depends on the type of solvent. The highest 2PA cross sections are obtained in solvents of medium polarity and values as high as 1420 GM are reported.
- Cvejn,Michail,Seintis,Klikar,Pytela,Mikysek,Almonasy,Ludwig,Giannetas,Fakis,Bure?
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p. 12819 - 12828
(2016/02/12)
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- NOVEL COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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Disclosed are: an organic electroluminescent element compound represented by structural formula 1 or 2 below; and an organic electroluminescent element comprising same. In this way, it is possible to provide an organic electroluminescent element compound which can be used as a host, hole-transport material and electron-transport material that has outstanding electrical stability and electron- and hole-transporting ability, a high level of triplet state energy and is able to improve the light-emitting efficiency of phosphorescent light-emitting materials, and an organic electroluminescent element.
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- Sonochemically synthesis of arylethynyl linked triarylamines catalyzed by CuI nanoparticles: A rapid and green procedure for Sonogashira coupling
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A simple and green method was performed to the preparation of copper iodide nanoparticles by ultrasound approach. Consequently the synthesis of aryl ethynyl linked triarylamines was carried out through the Sonogashira coupling between iodo-substituted triarylamine and aryl acetylenes in the presence of CuI nanoparticles/Pd(PPh3)2Cl2 as an efficient catalytic system and triethylamine as the base under ultrasonic irradiation. Good to excellent yields of products and short reaction times are some of the important advantages of this solvent free protocol which were attained by both nano CuI and ultrasound conditions.
- Safaei-Ghomi, Javad,Akbarzadeh, Zeinab
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p. 365 - 370
(2014/11/08)
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- The effect of porphyrins suspended with different electronegative moieties on the photovoltaic performance of monolithic porphyrin-sensitized solar cells with carbon counter electrodes
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Three D-π-A porphyrin sensitizers with different electronegative moieties (2,4,6-triphenyl-1,3,5-triazine, carbazole and triphenylamine) attached at the meso-position were designed and synthesized for monolithic dye-sensitized solar cells based on mesoscopic carbon counter electrodes. The effects of these different electronegative moieties on the photophysical, electrochemical and accordingly photovoltaic performance of the corresponding devices were investigated systematically. Electrochemical measurements indicate that the HOMO and LUMO energy levels could be tuned through the introduction of different electronegative groups onto the backbone of D-π-A porphyrin molecules. Current-voltage characteristics indicate that the Jsc and Voc of the DSSCs based on WH-C3, WH-C4 and WH-C5 increase as the electron-donating ability of their donors enhance in the order of WH-C3 sc) of 11.43 mA cm-2, an open circuit voltage (Voc) of 633.84 mV, and a fill factor (FF) of 0.69, corresponding to an overall conversion efficiency (η) of 5.00%.
- Chen, Jiangzhao,Ko, Songguk,Liu, Linfeng,Sheng, Yusong,Han, Hongwei,Li, Xiong
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p. 2889 - 2900
(2015/04/22)
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- Push-pull 1,8-naphthalic anhydride with multiple triphenylamine groups as electron donor
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In this paper, the push-pull molecules consisting of different number of triphenylamino groups and 1,8-naphthalic anhydride ring were designed and synthesized. The UV-vis absorption and emission spectra of these compounds were recorded. Along with the inc
- Wang, Limin,Shi, Yan,Zhao, Yingyuan,Liu, Heyuan,Li, Xiyou,Bai, Ming
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supporting information
p. 339 - 346
(2014/01/06)
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- High performance asymmetrical push-pull small molecules end-capped with cyanophenyl for solution-processed solar cells
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Two novel asymmetrical push-pull small molecules have been synthesized successfully, consisting of triphenylamine and diketopyrrolopyrrole as a fundamental dipolar D-π-A structure with ethynylbenzene as the π-bridge. TPATDPPCN end-capped with cyanophenyl exhibits a low optical band gap of 1.65 eV, and an impressive PCE of 5.94% has been achieved. This journal is the Partner Organisations 2014.
- Gao, Hang,Li, Yanqin,Wang, Lihui,Ji, Changyan,Wang, Yue,Tian, Wenjing,Yang, Xichuan,Yin, Lunxiang
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supporting information
p. 10251 - 10254
(2014/08/18)
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- A visible-light-mediated synthesis of carbazoles
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The photosynthetic preparation of N-aryl- and N-alkyl-bearing carbazoles utilizes continuous flow, visible light, and an in situ formed Cu-based sensitizer (see picture). The method is mild and efficient, and allows the straightforward synthesis of a variety of carbazoles with different substituents, heterocycles, and complex carbon architectures. Copyright
- Hernandez-Perez, Augusto C.,Collins, Shawn K.
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supporting information
p. 12696 - 12700
(2013/12/04)
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- Arylamino-functionalized fluorene- and carbazole-based copolymers: Color-tuning their CdTe nanocrystal composites from red to white
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Four alternating arylamino-functionalized copolymers were synthesized in a Suzuki copolymerization applying 4, 4′-(2,7-dibromo-9H-fluorene-9,9-diyl) dianiline, 4,4′-(2,7-dibromo-9H-fluorene-9,9-diyl)bis(N,N-diphenylaniline) , 4-(3,6-dibromo-9H- carbazol-9
- Kanelidis, Ioannis,Ren, Yi,Lesnyak, Vladimir,Gasse, Jan-Christoph,Frahm, Ronald,Eychmueller, Alexander,Holder, Elisabeth
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experimental part
p. 392 - 402
(2012/01/06)
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- Synthesis and spectroscopic study of diphenylamino-substituted phenylene-(poly)ethynylenes: remarkable effect of acetylenic conjugation modes
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A series of diphenylamino-substituted phenylene-(poly)ethynylenes were successfully synthesized by a combination of Sonogashira coupling and double elimination protocol of β-substituted sulfones. When UV-light was irradiated, the amino-substituted phenylene-(poly)ethynylene emitted strong luminescence. The emission underwent a large bathochromic shift in polar solvent because of stabilization of their charge-separated excited states. Analyses of fluorescence life times of aminoacetylenes revealed that radiationless process was suppressed in the polar solvent CH2Cl2, resulting in high quantum yields.
- Fang, Jing-Kun,An, De-Lie,Wakamatsu, Kan,Ishikawa, Takeharu,Iwanaga, Tetsuo,Toyota, Shinji,Matsuo, Daisuke,Orita, Akihiro,Otera, Junzo
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supporting information; experimental part
p. 917 - 920
(2010/05/03)
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- Molecular wires comprising π-extended ethynyl- and butadiynyl-2,5- diphenyl-1,3,4-oxadiazole derivatives: Synthesis, redox, structural, and optoelectronic properties
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2,5-Diphenyl-1,3,4-oxadiazole (OXD) derivatives with terminal ethynyl- (4a,b) and butadiynyl-(8a,b) substituents have been synthesized in high yields. 2-Methyl-3,5-hexadiyn-2-ol has not been exploited previously in the synthesis of terminal butadiynes. Cr
- Wang, Changsheng,Palsson, Lars-Olof,Batsanov, Andrei S.,Bryce, Martin R.
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p. 3789 - 3799
(2007/10/03)
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- Mechanism and Models for Copper Mediated Nucleophilic Aromatic Substitution. 2. A Single Catalytic Species from Three Different Oxidation States of Copper in an Ullmann Synthesis of Triarylamines
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Ullmann condensations of diarylamines with iodobenzenes has been investigated under homogeneous and a heterogeneous catalytic conditions with cupruos and cupric salts, as well as powered copper metal.Copper catalyzed condensation of diarylamines with iodoaromatics is relatively insensitive to substituent (for substituted iodobenzenes p=-0.25; for substituted diphenylamines p=1.09) but quite sensitive to halogen (k1/kBr.200).The first direct evidence for solution catalysis after filtration of a metal catalyzed reactions was obtained.Quantitative analysis of reaction rates, product yields, and catalyst characteristics leads to a comprehensive picture of the formation of soluble cuprous ions as the single active catalytic species under all conditions investigated.This hypothesis rationalizes many of the perplexing results which typify the literature associated with copper catalyzed nucleophilic aromatic substitution.
- Paine, Anthony James
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p. 1496 - 1502
(2007/10/02)
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