- Synthesis of Thiophene-Based Optical Ligands That Selectively Detect Tau Pathology in Alzheimer's Disease
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The accumulation of protein aggregates is associated with many devastating neurodegenerative diseases and the development of molecular ligands able to detect these pathological hallmarks is essential. Here, the synthesis of thiophene based optical ligands
- Shirani, Hamid,Appelqvist, Hanna,B?ck, Marcus,Klingstedt, Therése,Cairns, Nigel J.,Nilsson, K. Peter R.
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- Rapid and sensitive detection of hypochlorite in ~100% aqueous solution using a bithiophene-based fluorescent sensor: Application to water analysis and live-cell imaging
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A new bithiophene-based biocompatible fluorescent and colorimetric sensor 2TD capable of detecting hypochlorite (ClO?) in enviro/biosystem was successfully synthesized. This sensor 2TD underwent a highly specific and sensitive oxidation reaction with ClO? and produced a bithiophene aldehyde (2T-CHO) emitting strong blue fluorescence, which was strongly confirmed by 1H NMR, HRMS, FTIR and DFT calculation. The 2TD for detecting ClO? displays an ultra-fast response (25 s), great water-solubility (~100% aqueous solution), wide pH working range (7–11), excellent anti-interference capability, and ultra-sensitivity with low detection limit of 8.3 nM. Colorimetric test strips demonstrate that 2TD can be utilized as a cost-effective and efficient solid-state sensor for rapidly and conveniently sensing ClO? with great sensitivity in practical applications. With the robust applicability, the 2TD was successfully utilized to determine/image ClO? in environmental water and live-cells. More interestingly, this developed sensor 2TD could be used as an efficient test tool for ClO? sensing.
- Chen, Jianbin,Hu, Tingting,Li, Chunpeng,Li, Tianduo,Niu, Qingfen,Qin, Xuyang,Wei, Tao,Yin, Pengcheng
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- Novel protein kinase C inhibitors: Synthesis and PKC inhibition of β- substituted polythiophene derivatives
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A series of β-substituted polythiophene derivatives was synthesized through palladium-catalyzed coupling reaction. Their structure-protein kinase C (PKC) inhibitory activity relationship was studied. The carboxaldehyde and hydroxymethyl derivatives of α-terthiophene were potent PKC inhibitors (IC50 = 10-7 M).
- Xu, Wei-Chu,Zhou, Qin,Ashendel, Curtis L.,Chang, Ching-Te,Chang, Ching-Jer
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- A novel dual-function bithiophene-Meldrum's acid based chemosensor for highly sensitive, colorimetric and fluorimetric detection of cyanide and hypochlorite and its applications
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A dual-function bithiophene-Meldrum's acid based chemosensor 2TM was developed, which displayed ultrafast, colorimetric and fluorescence turn-on responses for CN? and ClO? with specific selectivity and high sensitivity. The sensor 2TM for CN? detection in DMSO/H2O (1/3, V/V) solution was based on the nucleophilic addition of CN? to sensor, which resulted in remarkable spectral and discernible color changes. Meanwhile, 2TM showed specific selectivity for ClO? in 100percent aqueous solution based on the sensing mechanism of oxidative cleavage of C[dbnd]C bond. The detection limits were obtained to be 0.96 μM for CN? and 48 nM for ClO?. The sensing mechanism of 2TM toward CN? and ClO? was investigated by job'plot, FTIR, 1H NMR, HRMS and optical spectra. The sensor 2TM loaded colorimetric test strips/supported silica measurements demonstrated to be a portable, eco-friendly and ultrafast device for real-time and on-site visual detection of CN? and ClO? in water by the naked eye. More importantly, sensor 2TM with excellent photophysical properties and low biotoxicity was successfully applied to detect CN? and ClO? in live cells and environmental water samples, as well as capable of monitoring CN? in the natural food samples, illustrating its practical utility in biological and environmental systems.
- Chen, Jianbin,Hu, Tingting,Li, Chunpeng,Li, Tianduo,Niu, Qingfen,Qin, Xuyang,Wei, Tao,Yang, Lan
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- Photophysical, crystallographic, and electrochemical characterization of symmetric and unsymmetric self-assembled conjugated thiopheno azomethines
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Novel conjugated azomethines consisting uniquely of thiophene units are presented. The highly conjugated compounds were synthesized by simple condensation of a stable diamino thiophene (2) with its complementary thiophene aldehydes. These interesting nitrogen-containing thiophene units exhibit variable reactivity leading to controlled aldehyde addition. Because of the different amino reactivity, a one-pot synthesis of unsymmetric and symmetric conjugated azomethines with varying number of thiophene units was possible by judicious choice of solvent and careful control of reagent stoichiometry. The resulting covalent conjugated connections are both reductively and hydrolytically resistant. The thermodynamically E isomer is formed uniquely for all of the azomethines synthesized, which is confirmed by crystallographic studies. These also demonstrated that the azomethine bonds and the thiophene units are highly planar and linear. The fluorescence and phosphorescence of the thiopheno azomethines measured are similar to those of thiophene analogues currently used in functional devices, but with the advantage of low triplet formation and band-gaps as low as 1.9 eV. The time-resolved and steady-state temperature-dependent photophysics revealed the thiopheno azomethines do not populate extensively their triplet manifold by intersystem crossing. Rather, their excited-state energy is dissipated predominantly by nonradiative means of internal conversion. Quasi-reversible electrochemical radical cation formation of the thiophene units was found. These compounds further undergo electrochemically induced oxidative cross-coupling, resulting in conjugated products that also exhibit reversible radical cation formation.
- Guarin, Sergio Andres Perez,Bourgeaux, Marie,Dufresne, Stephane,Skene
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- Bithiophene-based fluorescent sensor for highly sensitive and ultrarapid detection of Hg2+ in water, seafood, urine and live cells
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Using Hg2+-promoted deprotection reaction, we have developed a new fluorescent turn-on sensor 2TS based on bithiophene fluorophore for Hg2+ detection. The sensing mechanism of 2TS towards Hg2+ was strongly proved by 1H NMR, FTIR, HRMS, UV–vis and fluorescence spectra. Remarkly, 2TS towards Hg2+ in 100% aqueous solution shows high sensitivity with a low detection limit of 19 nM, superior selectivity and ultra-rapid response of 20 s during a wide sensing pH range from 4 to 10. Taking advantage of the excellent properties, the low-cost sensor 2TS-based filter paper/TLC test strips were fabricated for visual, immediate and quantitative detection of Hg2+ in water, proving its applicability towards sensitive in-situ and on-site detection. Meanwhile, 2TS showed high analytical performance for Hg2+ detection in water, seafood as well as human urine samples. Moreover, thanks to the good water solubility, negligible cytotoxicity, good biocompatibility and cell-membrane permeability, 2TS was further applied to effectively image Hg2+ in live cells. Furthermore, the developed sensor 2TS acted as good fluorescent display material for Hg2+ with obvious color change.
- Chen, Jianbin,Li, Chunpeng,Li, Tianduo,Niu, Qingfen,Qin, Xuyang,Wang, Jingui,Wei, Tao,Yang, Qingxin
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- Anthelmintic activity of a nanoformulation based on thiophenes identified in Tagetes patula L. (Asteraceae) against the small ruminant nematode Haemonchus contortus
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The synthesis of thiophenic compounds, previously identified in Tagetes patula, revealed that 4-(5′-(hydroxymethyl)-[2,2′-bithiophene]-5-yl)but-3-yn-1-ol), or simply Thio1, has a pronounced in vitro anthelmintic effect against Haemonchus contortus, showing 100% efficacy in the egg hatch and larval development tests presenting EC50 = 0.1731 mg.mL?1 and EC50 = 0.3243 mg.mL?1, respectively. So, this compound was selected to preparation of a nanostructured formulation to be orally administered to Santa Inês sheep. In general, from the fecal egg count reduction test (FECRT), it was observed that the product kept the parasitic load in the digestive tract of the hosts stable, with eggs per gram of faeces (EPG) counts having a mean value mean = 2167.1, efficacy = 36,45%), thus protecting the animals from health risks caused by a massive nematode infestation. To better understand the mode of action of this thiophene derivative, in silico molecular modeling studies were carried out with the glutamate-activated chloride channel (GluCl), a well-known molecular target of anthelmintic compounds. Based on the affinity score (GlideScore = -5.7 kcal.mol?1) and the proposed binding mode, Thio1 could be classified as a potential GluCl ligand, justifying the promising results observed in the anthelmintic assays.
- Politi, Flávio Augusto Sanches,Bueno, Renata Vieira,Zeoly, Lucas André,Fantatto, Rafaela Regina,Eloy, Josimar de Oliveira,Chorilli, Marlus,Coelho, Fernando,Guido, Rafael Victório Carvalho,Chagas, Ana Carolina de Souza,Furlan, Maysa
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- Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells
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Two novel triads based on a diketopyrrolopyrrole (DPP) central core and two 4,4-difluoro-4-bora-3a,4a-diaza- s - indacene (BODIPY) units attached by thiophene rings have been synthesised having high molar extinction coefficients. These triads were characterised and used as donor materials in small molecule, solution processable organic solar cells. Both triads were blended with PC 71 BM as an acceptor in different ratios by wt % and their photovoltaic properties were studied. For both the triads a modest photovoltaic performance was observed, having an efficiency of 0.65%. Moreover, in order to understand the ground and excited state properties and vertical absorption profile of DPP and BODIPY units within the triads, theoretical DFT and TDDFT calculations were performed.
- Cortizo-Lacalle, Diego,Howells, Calvyn T.,Pandey, Upendra K.,Cameron, Joseph,Findlay, Neil J.,Inigo, Anto Regis,Tuttle, Tell,Skabara, Peter J.,Samuel, Ifor D. W.
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- Donor–acceptor (E)-2-[2-(2,2′-bithiophen-5-yl)vinyl]benzo[d]thiazole: synthesis, optical, electrochemical studies and charge transport characteristics
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Condensation of 2-methylbenzothiazole with 2,2′-bithiophene-5-carbaldehyde affords the title compound, a new chromophore. This compound was used for the doping of poly[9,9-bis(6-diethoxylphosphorylhexyl)fluorene], and the obtained composites demonstrated high electron mobility (1.50 × 10?4 cm2 V?1 s?1) in contrast to dopant-free matrixes.
- Tokarev, Sergey D.,Sotnikova, Yulia A.,Anisimov, Alexander V.,Fedorov, Yurii V.,Jonusauskas, Gediminas,Lypenko, Dmitriy A.,Malov, Vladimir V.,Tameev, Alexey R.,Mal'tsev, Eugene I.,Fedorova, Olga A.
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- Anchoring stability and photovoltaic properties of new D(-π-A) 2 dyes for dye-sensitized solar cell applications
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This study deals with the synthesis and characterization of two new di-anchoring dyes for applications in dye-sensitized solar cells. The materials were designed with a branched D(-π-A)2 structure containing (i) a rigid alkyl-functionalized carbazole core as the donor part, (ii) one (DYE1) or two (DYE2) thiophene units as the π-bridge and (iii) a cyano-acrylic moiety as acceptor and anchoring part. Electrochemical impedance spectroscopy indicated that the injected electron lifetime is higher in the case of DYE2, probably due to the length of the π-spacer that, in combination with the alkyl chain on the carbazole unit, hampers the charge recombination with the electrolyte. Stability tests on TiO2-sensitized films revealed that the di-anchoring remarkably slows down the desorption process, which conversely is evident for classic reference dyes. The highest power conversion efficiency reaches 5.01% in the case of DYE2 with a photovoltage of 0.70 V and a photocurrent of 10.52 mA cm-2, substantially deriving from a broader absorption with respect to DYE1, as also confirmed by IPCE measurements. These results support the efforts aimed at the structural engineering of D(-π-A)2 dyes to design new, more efficient and stable organic sensitizers.
- Grisorio, Roberto,De Marco, Luisa,Allegretta, Giovanni,Giannuzzi, Roberto,Suranna, Gian Paolo,Manca, Michele,Mastrorilli, Piero,Gigli, Giuseppe
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- Hexathianonaphyrin(1.0.0.1.0.0.1.0.0): Synthesis, optical, redox and protonation induced antiaromaticity
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A simple non-rigid precursor termed as a "triheterole"comprising of 2,2′-bithiophene linked to α-pyrrole was prepared using a four-step synthetic strategy. This functionalized triheterole was allowed to undergo acid catalyzed condensation in the presence
- Ajay, Jayaprakash,Sulfikarali, Thondikkal,Chakravarthy, Kakarlamudi Akhil,Reddy, Vennapusa Sivaranjana,Gokulnath, Sabapathi
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p. 484 - 492
(2021/04/07)
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- Synthesis and photoinduced charge stabilization in molecular tetrads featuring covalently linked triphenylamine-oligothiophene-BODIPY-C60
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Two covalently linked tetrads comprised of charge stabilizing triphenylamine (TPA)-oligothiophene (bi- or terthiophene, BT or TT) linked at the meso-position of a well-known photosensitizer, BF2-chelated boron dipyrromethene (BODIPY), was furth
- Benitz, Alejandro,D’Souza, Francis,Jang, Youngwoo,Nesterov, Vladamir,Thomas, Michael B
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- Discovery of novel “Dual-site” binding oseltamivir derivatives as potent influenza virus neuraminidase inhibitors
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From our research group, it was noticed that oseltamivir derivatives targeting 150-cavity of neuraminidase enzyme (NA) could significantly increase antiviral activity. Thus, we further enriched the C5–NH2 position of oseltamivir structure to ob
- Ai, Wei,Cherukupalli, Srinivasulu,Ding, Xiao,Huang, Bing,Jia, Ruifang,Jiang, Xiangyi,Li, Zhong,Liu, Xinyong,Ma, Xiuli,Sun, Lin,Sun, Zhuosen,Wang, Defeng,Zalloum, Waleed A.,Zhan, Peng,Zhang, Jian
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- Oxime ester photoinitiators containing five-membered heteroaromatic ring structure, and preparation and use thereof
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The invention relates to oxime ester compounds containing a five-membered heteroaromatic ring structure and represented by the formula (I) and (II), wherein m, n, n', A1, A2, R1, R2, R3, R4, R5, R6, R6'R7 and R7' are defined in the specification. The compounds represented by the formula (I) and (II) have excellent light absorption at 350-450 nm, can initiate the polymerization of acrylate monomersat low concentration, and have excellent thermal stability in the acrylate monomers, are oxime ester photoinitiators good in stability and suitable for a UV-Vis LED light source. The invention also relates to preparation of the compounds represented by the formula (I) and (II) and a use of the compounds represented by the formula (I) and (II) as photoinitiators or photosensitizers.
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Paragraph 0149; 0150
(2019/12/25)
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- Construction of 3,7-Dithienyl Phenothiazine-Based Organic Dyes via Multistep Direct C-H Arylation Reactions
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Herein, an effective and feasible approach to prepare 3,7-dithienyl phenothiazine-based organic dyes has been developed. In this synthetic procedure, the Pd-catalyzed multistep direct C-H arylation of thiophene derivatives with phenothiazine bromides was employed for the first time to construct the 3,7-dithienyl phenothiazine core scaffold, which greatly streamlines access to this class of organic dyes. 3-Thienyl phenothiazine-based dyes were also synthesized via the direct C-H arylation of thiophenes as references. Most of the 3,7-dithienyl phenothiazine-based dyes exhibit better photovoltaic performances than the 3-thienyl phenothiazine-based dyes. Among these organic dyes, the solar cell device based on 6d exhibits the highest conversion efficiency of 8.9%. Compared with 6d, organic dyes with longer π-conjugation, also including bithiophene as the π-spacer, show dramatically reduced conversion efficiencies of cell devices. The introduction of the more electron-rich 3,4-ethylenedioxythiophene to the C3- and/or C7-position of phenothiazine instead of thiophene does not significantly improve the photoelectric conversion performance. The highly efficient synthetic strategy herein developed and these primary results may be helpful to design and synthesize a variety of new 3,7-dithienyl phenothiazine-based organic dyes.
- Wang, Wen,Li, Xiaoyu,Lan, Jingbo,Wu, Di,Wang, Ruilin,You, Jingsong
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p. 8114 - 8126
(2018/06/11)
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- Thiophene-Based Organic D–π–A Dyes as Potent Sensitizers for Photodynamic Therapy
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In this study, synthetically readily accessible, thiophene-based organic D–π–A sensitizers exerted high phototoxicity and are valuable as sensitizer templates for use in photodynamic therapy (PDT). Evaluation of the antitumor activity of our previously sy
- Fuse, Shinichiro,Takizawa, Miori,Matsumura, Keisuke,Sato, Shinichi,Okazaki, Shigetoshi,Nakamura, Hiroyuki
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p. 5170 - 5177
(2017/09/23)
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- End-Capping Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C–H (Hetero)arylation
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A Pd-catalyzed C–H (hetero)arylation methodology has been optimized for the efficient synthesis of various useful end-capping groups that are widely applied in small-molecule optoelectronic materials. We report herein the synthesis of a broad scope of target molecules ranging from donor-type through acceptor-type to hybrid-type end-capping groups. To demonstrate their application in dye-sensitized solar cells, we have designed two new D–A–π–A′-type organic sensitizers (CYL-3 and CYL-4), which were synthesized in a step-economic manner by sequential C–H arylations using the facilely obtained end-capping groups. The devices based on CYL-3 and CYL-4 give Vocvalues of 0.67–0.71 V, Jscvalues of 10.07–11.63 mA cm–2, and FF values of 70.6–72.9 %, which correspond to overall power conversion efficiencies of 4.76–6.02 %. This work is expected to become a practical synthetic alternative allowing materials scientists to access small-molecule organic materials in fewer synthetic transformations.
- Lu, Te-Jui,Lin, Po-Han,Lee, Kun-Mu,Liu, Ching-Yuan
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p. 111 - 123
(2017/01/14)
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- METAL CHALCOGENIDE NANOSTRUCTURES
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A hybrid inorganic-organic composite comprising a nanostructure of a metal chalcogenide and at least one compound comprising an organic cyclic moiety, wherein the compound is linked to the nanostructure, is provided. A nanotube of metal chalcogenide (e.g., metal dichalcogenide) nanostructure having attached to at least one surface thereof one or more selected chemically reactive nanoparticles is also provided.
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Paragraph 0234; 0235; 0236
(2017/07/06)
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- Star-shaped D-π-A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: Synthesis and physical and photovoltaic properties
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Synthesis of a series of star-shaped oligomers having a novel electron donating tris(2-methoxyphenyl)amine (m-TPA) core, which is linked through a bithiophene or terthiophene π-bridge with electron-deficient alkyldicyanovinyl (alkyl-DCV) groups, is descri
- Luponosov, Yuriy N.,Min, Jie,Solodukhin, Alexander N.,Bakirov, Artem V.,Dmitryakov, Petr V.,Shcherbina, Maxim A.,Peregudova, Svetlana M.,Cherkaev, Georgiy V.,Chvalun, Sergei N.,Brabec, Christoph J.,Ponomarenko, Sergei A.
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p. 7061 - 7076
(2016/08/02)
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- A new polythiophene-driven coating method on an inorganic INT/IF-WS2 nanomaterial surface
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Inorganic nanotubes and fullerene nanoparticles of tungsten disulfide (INTs-WS2 and IFs-WS2, respectively) are practically inert, hindering their usefulness in both research and commercial applications. The covalent attachment of fun
- Raichman,Ben-Shabat Binyamini,Lellouche
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p. 4490 - 4504
(2016/01/29)
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- A benzo thiophene group-containing indole salt dye and its preparation and use
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The invention relates to a benzindole salt dye containing a thiophene group, which is as shown in formula (1) and has a relatively strong surface-enhanced Raman scattering (SERS) effect, and a preparation method and application of the benzindole salt dye. Cations of a benzindole salt are of a D-pi-A structure, dialkylamino is taken as an electron donor, nitrogen-containing heterocyclic benzindole cations are taken as electron acceptors, and thiophene vinyl is taken as a conjugated bridge respectively. Dye molecules with the structure can be compounded with nano-gold or silver particles to form an SERS marker for surface-enhanced Raman spectral detection, the SERS intensity is high, and the reaction is sensitive; and the absorption wavelength of the dye is controllable by regulating and controlling the length of a molecular conjugated chain, and the SERS dye molecules are expected to be applied in the field of biomedical spectral detection.
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Paragraph 0036-0038; 0042
(2017/04/11)
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- A molecular breakwater-like tetrapod for organic solar cells
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We report the synthesis and characterization of a tetrapodal breakwater-like small molecule, SO, containing a tetraphenylsilane core and four cyanoester functionalized terthiophene arms. SO possesses a deep lying HOMO energy level of -5.2 eV and a narrow bandgap of 1.9 eV. Absorption, X-ray scattering and differential scanning calorimetry (DSC) measurements indicate crystalline nature of this compound but very slow crystallization kinetics. Solar cells employing SO and phenyl-C61-butyric acid methyl ester (PCBM) were fabricated and evaluated. Relatively low performance was obtained mainly due to the lack of optimal phase separation under various processing conditions including thermal annealing, slow-cooling and solvent annealing. Addition of poly(thienylene vinylene) (PTV), poly(3-hexylthiophene) (P3HT) and a platinum-containing low bandgap conjugated polymer Pt-BODIPY, into the SO/PCBM blend was found to induce device favorable phase separation and the polymers were found to act as the primary hole conductor. Such ternary blend devices showed cooperatively improved performances over binary devices employing either SO or the individual conjugated polymer alone.
- Yang, Jianzhong,He, Wenhan,Denman, Kimberly,Jiang, Ying-Bing,Qin, Yang
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p. 2108 - 2119
(2015/02/05)
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- Bithiophene derivative for green organic light-emitting diode dopant and method for preparing the same
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A bithiophene derivative for green organic light-emitting diode dopant and method for preparing the same are provided to have an excellent thermal stability, color purity, and light efficiency and to have superior photophysical characteristics as a dopant
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Paragraph 0084-0089
(2020/04/01)
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- Phenothiazine derivatives-based D-π-A and D-A-π-A organic dyes for dye-sensitized solar cells
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D-π-A and D-A-π-A-structured organic dyes represent different developmental directions of photosensitizers in dye-sensitized solar cells (DSSCs). In this work, two phenothiazine derivatives-based D-π-A and D-A-π-A-structured organic dyes have been synthesized and applied in DSSCs. The physical and electrochemical properties of both dyes have been investigated systematically. The results show that the D-A-π-A-structured dye exhibits a broader spectrum response but lower molar coefficient of extinction when compared to the D-π-A-structured dye. Regarding photovoltaic performance, the D-π-A-structured dye yields a higher efficiency (η) of 7.5% with a higher short-circuit current density (Jsc) of 16.36 mA cm -2 and open-circuit voltage (Voc) of 706 mV than that of the D-A-π-A-structured dye. Incident photon-to-electron conversion efficiency (IPCE) studies and impedance analysis also support these results. These results demonstrate that the phenothiazine derivatives-based D-π-A-structured organic dyes can compete with, and even exceed, D-A-π-A-structured organic dyes under the same test conditions. The Royal Society of Chemistry 2014.
- Yang, Xichuan,Zhao, Jianghua,Wang, Lei,Tian, Jie,Sun, Licheng
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p. 24377 - 24383
(2014/06/24)
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- Synthesis and fluorescent properties of novel chiral 1,2-diaminocyclohexane substituted ligands and their complexes
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A series of novel chiral 1,2-diaminocyclohexane derivatives bearing heterocyclic units were synthesized via improved methods under ultrasonic irradiation. The photophysical properties of compounds were studied in ethanol, methanol, and chloroform. The sensitivity of these amines toward Cu 2+, Cd2+, and Ni2+ was studied by the UV-vis and fluorescent methods. The π-electron structure of thiophene and bithiophene containing sensors is the most active toward all above mentioned metal ions and is highly selective for Ni2+ and Cd2+.
- Meshkovaya, Violetta V.,Yudashkin, Alexander V.,Bushueva, Polina Y.,Eremeeva, Natalya B.,Klimochkin, Yuri N.
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supporting information
p. 3211 - 3217
(2014/05/06)
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- Triindole-cored star-shaped molecules for organic solar cells
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Two new triindole-cored star-shaped molecules SM-1 and SM-2 have been designed and synthesized, and their optical, electrochemical, thermal, transport and photovoltaic properties have been investigated in detail. SM-1 and SM-2 exhibited good thermal stability, intensive absorption in a broad region, and relatively high hole mobility. Photovoltaic performances of these two molecules were investigated by fabricating bulk heterojunction solar cell devices with a blend film of SM-1:PC71BM or SM-2:PC71BM as the active layer. Organic solar cells (OSCs) based on SM-1:PC71BM and SM-2:PC71BM gave power conversion efficiencies (PCEs) of 2.05% and 2.29%, respectively. A PCE of 2.29% is the best result for all the reported triindole-based photovoltaic materials, indicating that triindole-based small molecules could become promising donor materials for solution-processed OSCs.
- Lu, Zhen,Li, Cuihong,Fang, Tao,Li, Guangwu,Bo, Zhishan
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p. 7657 - 7665
(2013/07/26)
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- Synthesis, characterization and properties of novel star-shaped π-conjugated oligomers with triphenylamine core
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Four new star-shaped π-conjugated oligomers (TPA-CZ3, TPA-TPA3, TPA-PTZ3 and TPA-BT3) with triphenylamine as a core and different electron-donating ability groups, carbazole, triphenylamine, phenothiazine and bithiophene, as peripheral units have been designed and synthesized via the Heck reaction. These oligomers show good solubility in common organic solvents. Their photophysical, electrochemical, electronic structure and charge transfer properties between these star-shaped π-conjugated oligomers and N,N′-bis(1-ethylpropyl)-3, 4:9,10-perylene bis(tetracarboxyl diimide) (EP-PDI) have been investigated by UV-vis absorption spectra, photoluminescence (PL) spectra, cyclic voltammetry (CV) measurement, theoretical calculations and fluorescence quenching. The results show that the absorptions and fluorescences of TPA-CZ3, TPA-TPA3 and TPA-PTZ3 are red shifted with the electron-donating ability of the peripheral unit increasing from carbazole to triphenylamine and phenothiazine. In addition, although the bithiophene group has a weaker electron-donating ability than carbazole, triphenylamine and phenothiazine, the absorption and fluorescence of TPA-BT3 have a red shift than those of TPA-CZ3, TPA-TPA3 and TPA-PTZ3 because TPA-BT3 has a longer conjugation length than TPA-CZ3, TPA-TPA3 and TPA-PTZ3. The triphenylamine core and the peripheral units can constitute a large conjugated structure. The fluorescence quenching properties indicate that efficient charge transfer can happen between the star-shaped oligomers and EP-PDI. The core of these new star-shaped oligomers is electron-donating group, triphenylamine. The peripheral units are four hole-transporting chromophores with different electron-donating ability. The photophysical properties of these oligomers can be tuned through changing the electron-donating ability and conjugation length of the peripheral units.
- Liu, Leijing,Guo, Qing,Li, Jiyang,Yao, Bin,Tian, Wenjing
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p. 456 - 464
(2013/08/25)
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- Synthesis of π-conjugated 2,2:6′,2″-terpyridine-substituted oligomers based on 3,4-ethylenedioxythiophene
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Dissymmetric π-conjugated monomers and oligomers incorporating 3,4-ethylenedioxythiophene (EDOT) units and bearing terpyridine end groups were synthesized in good yields through Vilsmeyer-Haak formylation followed by a reaction with 2-acetylpyridine in ba
- Fillaud, Laure,Trippé-Allard, Ga?lle,Lacroix, Jean Christophe
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p. 1028 - 1031
(2013/04/23)
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- Cyclic thiourea/urea functionalized triphenylamine-based dyes for high-performance dye-sensitized solar cells
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Six cyclic thiourea/urea functionalized triphenylamine-based dyes (AZ1-AZ6) containing 2-cyanoacrylic acid as an acceptor and various linkers (phenyl, biphenyl, and bithiophene) were synthesized. They exhibited high photovoltaic performance owing to an improved short-circuit photocurrent density (J sc) and open-circuit voltage (Voc). Among them, AZ6 bearing a cyclic thiourea group and bithiophene linker showed the highest power conversion efficiency (PCE) up to 7.29%, which was comparable to that of N719 (PCE = 7.36%).
- Wu, Zhisheng,An, Zhongwei,Chen, Xinbing,Chen, Pei
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supporting information
p. 1456 - 1459
(2013/07/05)
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- Synthesis of some green dopants for OLEDs based on arylamine 2,3-disubstituted bithiophene derivatives
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A series of green dopants based on 2,2-diphenylvinyl end-capped bithiophene and three different arylamine moieties (9-phenylcarbazole, triphenylamine, and N,N'-di-(ptolyl) benzeneamine) were successfully synthesized by the Suzuki and Wittig coupling react
- Song, Mi-Seon,Nguyen, Quynh Pham Bao,Song, Chang-Hyun,Lee, Duckhee,Chai, Kyu Yun
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p. 14033 - 14041
(2014/01/06)
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- Efficient synthesis of RITA and its analogues: Derivation of analogues with improved antiproliferative activity via modulation of p53/miR-34a pathway
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A novel approach to synthesize RITA by practical palladium-catalyzed C-C bond-forming Suzuki reactions at room temperature was developed, which was used for deriving a series of substituted tricyclic α-heteroaryl (furan/thiophene) analogues of RITA under mild conditions. These novel analogues showed notable antiproliferative activity against cancer cell lines with wild-type p53 (i.e., HCT116, A549, MCF-7 and K562), but much less activity in HCT116/p53-/- cells. In particular, compound 1f demonstrated promising antiproliferative activity compared to RITA, with IC50 = 28 nM in MCF-7 vs. 54 nM for RITA, and cancer cell selectivity. Compound 1f markedly activated p53 in HCT116 cells at 100 nM, triggering apoptosis. Importantly, we found that both RITA and compound 1f induced G 0/G1 cell cycle arrest by up-regulating miR-34a, which in turn down-regulated the expression of cell cycle-related proteins CDK4 and E2F1. In summary, this study reports an effective synthetic approach for RITA and its analogues, and elucidates a novel antiproliferative mechanism of these compounds. The Royal Society of Chemistry 2012.
- Lin, Jinshun,Jin, Xiuli,Bu, Yiwen,Cao, Deliang,Zhang, Nannan,Li, Shangfu,Sun, Qinsheng,Tan, Chunyan,Gao, Chunmei,Jiang, Yuyang
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p. 9734 - 9746
(2013/01/16)
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- COMPOSITIONS AND METHODS FOR THE TREATMENT OF PATHOLOGICAL CONDITION(S) RELATED TO GPR35 AND/OR GPR35-HERG COMPLEX
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Disclosed are compositions and methods for the prevention and/or treatment of diseases which are pathophysiologically related to GPR35, and/or GPR35-hERG signaling complex. For example, disclosed are compounds for preventing and/or treating diseases which are pathophysiologically related to GPR35 in a subject. The compounds having a formula (I), (II) or (III):
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Page/Page column 55
(2012/02/03)
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- Electronic properties of thienylene vinylene oligomers: Synthesis and theoretical study
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(E)-1,2-bis(2-thienyl)vinylene (TV), (E)-1,2-bis (3-octyl-2-thienyl) vinylene (TOV), (E)-1,2-bis(3-(2-ethylhexyl)-2-thienyl)vinylene (T2EHV), and (E)-1,2-bis-[2,2'-bithienyl] vinylene (BTV) have been synthesized by a combination of formylation reaction and Mc Murry dimerization. UV-Vis spectra of BTV showed the longest wavelength absorption, TOV and T2EHV showed a bathochromic shift to the red compared with TV, due to an increment of delocalization of the conjugated p-system as the result of the weakening of the carbon-carbon double bonds of the thienyl rings due to the substitution of one hydrogen by the alkyl group. Based on optical data, the effect of linear and branched alkyl chain and extension of conjugation length on the electronic properties is discussed. 1H, 13C-NMR, UV-Visible, Fluorescence data are discussed and theoretical DFT and TD-DFT calculations of ground state and excited states have been also considered in the analysis and explanation of results. Springer Science+Business Media, LLC 2012.
- Neculqueo,Rojas Fuentes,Lopez,Matute,Vasquez,Martinez
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p. 1751 - 1760
(2013/03/14)
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- Synthesis of sterically hindered antipyrines for intramolecular charge transfer facilitated sensing
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A new series of sterically hindered antipyrine derivatives have been synthesized by Schiff base condensation for potential fluorescence sensing applications. Their optical, thermal, and electrochemical properties were fully characterized. Broad absorption spectra were observed as a result of the strong intramolecular charge transfer between antipyrine and sterically hindered conjugated moiety. Reversible one electron oxidation couple was observed for most compounds, with carbazole, phenothiazine, and bithiophene functionalized derivatives exhibiting extra reversible one one-electron oxidation process at higher positive potentials. Cabazole functionalized antipyrine derivative APCZ presents good fluorescence sensing for Co2+ and Cu2+, with 3.41-fold enhancement in fluorescence intensity and 2-fold enhancement in fluorescence quantum yield observed. Copyright
- Bian, Linyi,Sun, Gang,Sun, Yuxi,Tang, Weihua
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supporting information
p. 1112 - 1118
(2013/08/24)
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- Fluorene-containing organic photosensitizers for dye-sensitized solar cells
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Seven new donor-spacer-acceptor metal-free organic dyes containing a fluorene and/or thiophene unit as a conjugated spacer are prepared and their physicochemical properties as well as photovoltaic performance are studied. The electron transfer from donor to acceptor upon excitation of these dyes is sensitive to the conjugated spacers. If a stronger donor moiety such as (ethylenedioxy)thiophene is used as a spacer, such as in F-E1 dye, the dye molecule has a better charge separation and therefore high efficiency. Furthermore, for the same donor and acceptor, fluorene is a better conjugated spacer than the bithiophene moiety because of its nonplanar conformation, which avoids the electron-hole recombination of dye upon photoexcitation. Short molecules with planar conformation aggregate easily, and the corresponding device reveals low open-circuit voltage Voc. On the other hand, dye molecules with long alkyl side chains (large size) adsorb less on the TiO 2 electrode, which results in a smaller short-circuit current density Jsc. The difference in the efficiency of these dyes is small except for F-1 (owing to its short conjugation length), and electron density difference map analyses reveal that photoexcitation transfer of electron density from the donating moieties toward the acceptor/anchoring units occurs for all molecules. The small difference in the efficiency is attributed partly to the degree of effective charge transfer upon excitation, not totally to the absorption profile of the dye molecules. Furthermore, time-dependent DFT simulated absorption spectra are in excellent agreement with experimental spectra when the dyes are in their protonated states in THF solution. The transition probability calculated with the electron density difference analyses combined with the absorption data and photovoltaic performance provide useful information for designing organic sensitizers for dye-sensitized solar cells.
- Wu, Chun-Guey,Chung, Ming-Fong,Tsai, Hui-Hsu Gavin,Tan, Chun-Jui,Chen, Su-Chien,Chang, Chiao-Hsin,Shih, Ting-Wen
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p. 832 - 843
(2013/01/15)
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- Fluorene-containing organic photosensitizers for dye-sensitized solar cells
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Seven new donor-spacer-acceptor metal-free organic dyes containing a fluorene and/or thiophene unit as a conjugated spacer are prepared and their physicochemical properties as well as photovoltaic performance are studied. The electron transfer from donor to acceptor upon excitation of these dyes is sensitive to the conjugated spacers. If a stronger donor moiety such as (ethylenedioxy)thiophene is used as a spacer, such as in F-E1 dye, the dye molecule has a better charge separation and therefore high efficiency. Furthermore, for the same donor and acceptor, fluorene is a better conjugated spacer than the bithiophene moiety because of its nonplanar conformation, which avoids the electron-hole recombination of dye upon photoexcitation. Short molecules with planar conformation aggregate easily, and the corresponding device reveals low open-circuit voltage Voc. On the other hand, dye molecules with long alkyl side chains (large size) adsorb less on the TiO2 electrode, which results in a smaller short-circuit current density Jsc. The difference in the efficiency of these dyes is small except for F-1 (owing to its short conjugation length), and electron density difference map analyses reveal that photoexcitation transfer of electron density from the donating moieties toward the acceptor/anchoring units occurs for all molecules. The small difference in the efficiency is attributed partly to the degree of effective charge transfer upon excitation, not totally to the absorption profile of the dye molecules. Furthermore, time-dependent DFT simulated absorption spectra are in excellent agreement with experimental spectra when the dyes are in their protonated states in THF solution. The transition probability calculated with the electron density difference analyses combined with the absorption data and photovoltaic performance provide useful information for designing organic sensitizers for dye-sensitized solar cells.
- Wu, Chun-Guey,Chung, Ming-Fong,Tsai, Hui-Hsu Gavin,Tan, Chun-Jui,Hilmersson, Su-Chien,Chang, Chiao-Hsin,Shih, Ting-Wen
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p. 832 - 843
(2014/01/17)
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- Synthesis of functionalized 2-arylthiophenes with triarylbismuths as atom-efficient multicoupling organometallic nucleophiles under palladium catalysis
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Atom-efficient cross-coupling reactions of functionalized 2-bromo- and 2-iodothiophenes have been demonstrated using triarylbismuths as atom-efficient multicoupling organometallic nucleophiles under palladium-catalyzed conditions. These couplings with various functionalized triarylbismuths proceeded smoothly to afford the corresponding functionalized 2-arylthiophenes in high yields. Georg Thieme Verlag Stuttgart · New York.
- Rao, Maddali L. N.,Banerjee, Debasis,Dhanorkar, Ritesh J.
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supporting information; experimental part
p. 1324 - 1330
(2011/07/07)
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- Novel (E)-5-styryl-2,2′-bithiophene derivatives as ligands for β-amyloid plaques
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In continuation of our investigation on the bithiophene structure as potential β-amyloid probes, a series of (E)-5-styryl-2,2′-bithiophene (SBTP) derivatives was designed and synthesized. In vitro binding showed that all of them displayed high binding affinities to Aβ1-42 aggregates (Ki = 0.10-41.05 nM). Moreover, two radio-iodinated probes, [125I]-(E)-5-(4-iodostyryl)-2,2′-bithiophene ([ 125I]8) and [125I]-(E)-5-iodo-5′-(4-methoxystyryl)- 2,2′-bithiophene ([125I]31) were prepared. Both of them displayed specific labeling of Aβ plaques in the brain sections of AD model mice with low background. In vivo biodistribution in normal mice indicated that [125I]8 exhibited high initial brain uptake (2.11% ID/g at 2 min) and rapid clearance (0.41% ID/g at 30 min). These preliminary results suggest that SBTP derivatives may be served as novel β-amyloid imaging probes.
- Cui, Mengchao,Li, Zijing,Tang, Ruikun,Jia, Hongmei,Liu, Boli
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experimental part
p. 2908 - 2916
(2011/07/08)
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- Synthesis of 2,2-bithiophene based dye sensor and optical properties toward metal cations
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We have designed and synthesized a 2,2-bithiophene-based new dye chemical sensor, and its selective and sensitive recognizing functions toward heavy metal cations were investigated. These find results were characterized using UV-Vis. spectrophotometer and spectrofluorometer. In addition, electrochemical properties were measured with cyclicvoltammetry test. Electron density distributions and HOMO/LUMO energy levels were computationally calculated and optimized. The energy levels of HOMO/LUMO were compared with computational calculation and cyclicvoltammetry measurement for each value. Finally, the formation type of metal ion bindings was determined by Job's plot measurements.
- Kim, Young-Sung,Son, Young-A.
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experimental part
p. 163 - 171
(2012/05/04)
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- Structure-property relationship of acceptor-substituted oligothiophenes
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A series of oligothiophenes that are end-capped with dicyanovinyl (DCV) and 1,3,2-(2H)-dioxaborine (DOB) moieties has been prepared using standard procedures. Their optoelectronic properties have been investigated by cyclic voltammetry and optical absorption. The optical absorption has been measured both in solution and thin film state.
- Wrackmeyer,Hummert,Hartmann,Riede,Leo
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scheme or table
p. 8729 - 8733
(2010/12/25)
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- Synthesis and evaluation of novel benzothiazole derivatives based on the bithiophene structure as potential radiotracers for β-amyloid plaques in Alzheimer's disease
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In this study, six novel benzothiazole derivatives based on the bithiophene structure were developed as potential β-amyloid probes. In vitro binding studies using Aβ aggregates showed that all of them demonstrated high binding affinities with Ki/sub
- Cui, Meng-Chao,Li, Zi-Jing,Tang, Rui-Kun,Liu, Bo-Li
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experimental part
p. 2777 - 2784
(2010/07/04)
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- An efficient synthesis of 5′-(4-cyanophenyl)-2,2′-bifuran-5- carbonitrile and analogues
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5′-(4-Cyanophenyl)-2,2‰-bifuran-5-carbonitrile (6a) was prepared by two approaches. The first approach involves four steps, employs Stille coupling conditions utilising 2-tributylstannylfuran and 5-bromofuran-2-carboxaldehyde to furnish 3a in excellent yi
- Ismail, Mohamed A.
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p. 733 - 737
(2007/10/03)
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- Novel highly fluorescent dendritic chiral amines: Synthesis and optical properties
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An efficient approach to dendritic chiral amines through the allylation of optically active imines bearing chiral auxiliaries were developed. The addition of allylic zinc catalyzed by CeC13·7H2O to chiral imines derived from 2-thiophenecarboxaldehyde and α-amino acid esters conveniently and efficiently afforded the corresponding homoallylic amines with excellent diastereoselectivity. Such addition reactions employing diimines or triimines of the polycyclic aromatic derivatives also produced the chrial multiallylic dendritic amines with the similar diastereoselectivity. The investigation of their photophysical properties including UV-vis absorption and fluorescence spectra as well as circular dichroism (CD) indicated that it did not affect the absorption of the precursors to induce the chiral auxiliaries; however, that the whole molecules exhibited the obvious CD behaviors.
- Wang, Hui,Wang, Jin-Liang,Yuan, Si-Chun,Pei, Jian,Pei, Wei-Wei
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p. 8465 - 8474
(2007/10/03)
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- Novel cyclopentane dicarboxamide sodium channel blockers as a potential treatment for chronic pain
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A series of new voltage-gated sodium channel blockers were prepared based on the screening lead succinic diamide BPBTS. Replacement of the succinimide linker with the more rigid cyclic 1,2-trans-diamide linker was well tolerated. N-Methylation on the biph
- Shao, Pengchang P.,Ok, Dong,Fisher, Michael H.,Garcia, Maria L.,Kaczorowski, Gregory J.,Li, Chunshi,Lyons, Kathryn A.,Martin, William J.,Meinke, Peter T.,Priest, Birgit T.,Smith, McHardy M.,Wyvratt, Matthew J.,Ye, Feng,Parsons, William H.
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p. 1901 - 1907
(2007/10/03)
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- Quater-, quinque-, and sexithiophene organogelators: Unique thermochromism and heating-free sol-gel phase transition
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A series of quater-, quinque-, and sexithiophene derivatives bearing two cholesteryl groups at the α-position, which are abbreviated as 4T-(chol)2, 5T-(chol)2, and 6T-(chol)2, respectively, have been synthesized. It has been found that these oligothiophene derivatives act as excellent organogelators for various organic fluids and show the unique thermochromic behaviors through the sol-gel phase transition. It was shown on the basis of extensive investigations, performed with UV-visible spectroscopy, circular dichroism (CD), transmission electron" microscopy (TEM), scanning electron microscopy (SEM), and atomic force microscopy (AFM), that these gelators self-assemble into the one-dimensional structures in the organogels, in which the π-block moieties of the oligothiophenes are stacked in an H-aggregation mode. Surprisingly, an AFM image shows that 4T-(chol) 2 forms unimolecular fibers in a left-handed helical sense, whereby one pitch of the helical fiber is constructed by 400-540 4T-(chol)2, molecules. Very interestingly, the conformational change in the oligothiophene moieties can be visually detected: for example, 6T-(chol)2 shows a specific absorption maximum in the gel (λmax = 389 nm) and in the solution (λmax = 439 nm). In addition, a sol-gel phase transition of the 6T-(chol)2 gel was implemented by addition of oxidizing and reducing reagents such as FeCl3 and ascorbic acid, respectively. The stimuli-responsive functionality of the oligothiophene-based organogels makes them promising candidates for switchable opto- and electronic soft materials.
- Kawano, Shin-Ichiro,Fujita, Norifumi,Shinkai, Seiji
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p. 4735 - 4742
(2007/10/03)
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- 1,2 DIAMIDO CYCLOALKYL SODIUM CHANNEL BLOCKERS
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1,2 Diamido cycloalkyl compounds that are sodium channel blockers; pharmaceutical compositions that include an effective amount of the aryl-link-aryl thiazolidin-dione and aryl-link-aryl oxazolodine-dione compounds and a pharmaceutically acceptable carrier; and a method of treatment of acute pain, chronic pain, visceral pain, inflammatory pain, or neuropathic pain, as well as irritable bowel syndrome, Crohns disease, epilepsy, partial and generalized tonic seizures, multiple sclerosis, bipolar disease, and tachy-arrhythmias by the administration of an effective amount of aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolodine-dione compounds, either alone, or in combination with one or more therapeutically active compounds, are described.
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- Effect of local molecular structure on the chain-length dependence of the electronic properties of thiophene-based π-conjugated systems
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Three series of thiophene-based π-conjugated oligomers built with different combinations of thiophene cycles and double bonds have been synthesized and characterized. The analysis of the chain length dependence of the electronic, electrochemical, and vibrational properties of the three series of oligomers has been carried out using cyclic voltammetry, UV-vis, IR, and Raman spectroscopies. These various investigations provide consistent results showing that incorporation of ethylenic linkages in an oligothiophene structure leads to a faster decrease of the HOMO-LUMO gap with chain extension due to the combined effects of enhanced planarity and lower overall aromatic character of the system. Although the incorporation of two consecutive double bonds in the system leads to a stabilization of the dicationic state, this structural modification does not produce the expected further decrease of the HOMO-LUMO gap at large chain extension. This phenomenon is discussed on the basis of an interplay between aromaticity and bond length alternation.
- Frère, Pierre,Raimundo, Jean-Manuel,Blanchard, Philippe,Delaunay, Jacques,Richomme, Pascal,Sauvajol, Jean-Louis,Orduna, Jesus,Garin, Javier,Roncali, Jean
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p. 7254 - 7265
(2007/10/03)
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- Design and synthesis of push-pull chromophores for second-order nonlinear optics derived from rigidified thiophene-based π-conjugating spacers
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Two series of push-pull chromophores built around thiophene-based π-conjugating spacers rigidified either by covalent bonds or by noncovalent intramolecular interactions have been synthesized and characterized by UV-vis spectroscopy, electric field induced second harmonic generation (EFISH) and differential scanning calorimetry. Comparison of the linear and second-order nonlinear optical properties of chromophores based on a covalently bridged dithienylethylene (DTE) spacer with those of their analogues based on open chain DTE shows that the rigidification of the spacer produces a considerable bathochromic shift of the absorption maximum together with a dramatic enhancement of the molecular quadratic hyperpolarizability (μΒ) which reaches values among the highest reported so far. A second series of NLO-phores has been derived from a 2,2′-bi(3,4-ethylenedioxythiophene) (BEDOT) π-conjugating spacer. As indicated by X-ray and UV-vis data, rigidification of the spacer originates in that case, from noncovalent intramolecular interactions between sulfur and oxygen atoms. Again, comparison with the parent compounds based on an unsubstituted bithiophene spacer reveals a marked red shift of the absorption maximum and a large enhancement of μΒ. In an attempt to distinguish the contribution of the electronic and geometrical effects of the ethylenedioxy group, a third series of NLO-phores based on 3,4-ethylenedioxythiophene (EDOT) and 3,4-dihexyloxythiophene spacers has been synthesized. Comparison with compounds based on unsubstituted thiophene shows that, despite a red shift ofλmax, introduction of alkoxy groups leads to a decrease of μΒ. Theoretical calculations indicate that this effect results from a decrease of the dipole moment (μ) caused by the auxiliary electron-donor alkoxy groups on the thiophene ring. In contrast, replacement of BT by BEDOT produces an increase of μ, which associated with the noncovalent rigidification of the BT system accounts for the observed enhancement of μΒ.
- Raimundo, Jean-Manuel,Blanchard, Philippe,Gallego-Planas, Nuria,Mercier, Nicolas,Ledoux-Rak, Isabelle,Hierle, Rolland,Roncali, Jean
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p. 205 - 218
(2007/10/03)
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- Push-pull chromophores based on 2,2′-bi(3,4-ethylenedioxythiophene) (BEDOT) π-conjugating spacer
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Replacement of 2,2′-bithiophene by BEDOT in push-pull NLO-phores produces a red shift of the absorption maximum accompanied with a large increase of the quadratic nonlinear optical susceptibility.
- Raimundo, Jean-Manuel,Blanchard, Philippe,Frère, Pierre,Mercier, Nicolas,Ledoux-Rak, Isabelle,Hierle, Rolland,Roncali, Jean
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p. 1507 - 1510
(2007/10/03)
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- Biheteroaryl inhibitors of farnesyl-protein transferase
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The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invent
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