- Synthesis and characterization of donor-acceptor type conducting polymers containing benzotriazole acceptor and benzodithiophene donor or: S -indacenodithiophene donor
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Two novel electrochromic copolymers, poly(benzodithiophene-benzotriazole) (PBDBT) and poly(s-indacenodithiophene-benzotriazole) (PIDBT) were synthesized successfully through Stille coupling reactions. Both polymers were characterized by cyclic voltammetry
- Zhang, Di,Wang, Min,Liu, Xiaoli,Zhao, Jinsheng
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- Redox-Active Peptide-Functionalized Quinquethiophene-Based Electrochromic π-Gel
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An electrochromic system based on a self-assembled dipeptide-appended redox-active quinquethiophene π-gel is reported. The designed peptide-quinquethiophene consists of a symmetric bolaamphiphile that has two segments: a redox-active π-conjugated quinquethiophene core for electrochromism, and peptide motif for the involvement of molecular self-assembly. Investigations reveal that self-assembly and electrochromic properties of the π-gel are strongly dependent on the relative orientation of peptidic and quinquethiophene scaffolds in the self-assembly system. The colors of the π-gel film are very stable with fast and controlled switching speed at room temperature.
- Konda, Maruthi,Maiti, Sayan,Jadhav, Rohit G.,Das, Apurba K.
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- Synthesis of a benzotriazole bearing alternating copolymer for organic photovoltaic applications
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A low band gap donor-acceptor (D-A) copolymer PTBTBDT, namely, poly(2-dodecyl-4,7-di(thiophen-2-yl)-2H-benzo[d][1,2,3]triazole-alt-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b′]dithiophene), was designed and synthesized via a Pd-catalyzed Stille polycondensation reaction. The polymer was characterized using 1H NMR spectroscopy, UV-vis absorption spectroscopy, cyclic voltammetry, and gel permeation chromatography (GPC). PTBTBDT has good solubility in common organic solvents, good thermal stability, broad absorption, low band gap and exhibits not only high hole mobility but also moderate photovoltaic properties. PTBTBDT displays broad absorption in the wavelength range from 300 nm to 630 nm, and its HOMO and LUMO energy levels were calculated to be -4.98 eV and -3.34 eV, respectively. Bulk heterojunction solar cells were fabricated using PTBTBDT as the electron donor and PC70BM as the acceptor. The device exhibits a power conversion efficiency of 2.12% with a current density of 5.45 mA cm-2, an open-circuit voltage of 0.72 V, and a fill factor of 54% under the illumination of AM 1.5 G, 100 mW cm-2. Under similar device fabrication conditions, the PTBTBDT based device showed considerably improved efficiency among its previously synthesized counterparts, i.e. PBDTDTBTz and PBDTBTz based devices, which have 1.7% and 1.4% efficiencies, respectively. The hole mobility of the PTBTBDT: PC70BM (1:2 w/w) blend reached up to 1.47 × 10-3 cm2 V-1 s-1 as calculated by the space-charge-limited current (SCLC) method. By side-chain engineering, this study demonstrates a good example of tuning the absorption range, energy level, charge transport, and photovoltaic properties of polymers.
- Istanbulluoglu, Cagla,G?ker, Seza,Hizalan, Gonul,Hacioglu, Serife O.,Udum, Yasemin Arslan,Yildiz, Esra D.,Cirpan, Ali,Toppare, Levent
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- Fused structures in the polymer backbone to investigate the photovoltaic and electrochromic properties of donor-acceptor-type conjugated polymers
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In this study, two new benzotriazole (BTz) and dithienothiophene (DTT) containing conjugated polymers were synthesized. After successful characterizations of the monomers by proton-nuclear magnetic resonance ( 1H NMR) and carbon-NMR (13C NMR) techniques, poly(4-(dithieno[3, 2-b:2′,3′-d]thiophen-2-yl)-2-(2-octyldodecyl)- 2H-benzo[d][1,2,3] triazole) P1 and poly(4-(5-(dithieno[3,2-b:2′,3′- d]thiophen-2-yl)thiophen-2-yl)-2-(2-octyldodecyl)-7-(thiophen-2-yl)-2H-benzo[d] [1,2,3]triazole) P2 were synthesized via a typical Stille coupling. Electrochemical and spectroelectrochemical studies showed that both polymers can be multipurpose materials and used in electrochromic and photovoltaic applications. Reported study indicated that incorporation of DTT into the structure leads to fast switching times compared with BTz-based polymers and competent percentage transmittance in the near-infrared region. Multichromism is important in the context of low-cost flexible display device technology and both polymers are ambipolar and processable as well as multichromic. Throughout the preliminary photovoltaic studies, the best performances of photovoltaic devices were found as Voc = 0.49 V, Jsc = 0.83 mA/cm 2, fill factor (FF) = 34.4%, and power conversion efficiency (PCE) = 0.14% for P1, and as Voc = 0.35 V, Jsc = 1.57 mA/cm 2, FF = 38.2%, and PCE = 0.21% for P2. 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013 Benzotriazole- and dithienothiophene-based conjugated polymers were synthesized via Stille coupling. Electrochemical and optical properties of the polymers indicated that the polymers can be great candidates for photovoltaic and electrochromic applications. Therefore, spectroelectrochemical, cyclic voltammetry, and preliminary photovoltaic studies are performed and the results of the studies are highlighted. Copyright
- Cevher, Sevki Can,Unlu, Naime Akbasoglu,Ozelcaglayan, Ali Can,Apaydin, Dogukan Hazar,Udum, Yasemin Arslan,Toppare, Levent,Cirpan, Ali
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- Two-Dimensional Halide Perovskite Materials
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The present disclosure relates to novel two-dimensional halide perovskite materials, and the method of making and using the two-dimensional halide perovskite materials.
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Paragraph 0134-0135
(2021/11/05)
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- Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges
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Four novel benzo[c][1,2,5]thiadiazole comprising monomers namely 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBTT), 5-fluoro-4,7-bis(4-hexylthiophen-2-yl)-6-((2-octyldodecyl)oxy)benzo[c][1,2,5]thiadiazole (HTBTHT), 5-fluoro-4,7-di(furan-2-yl)-6-((2-octyldodecyl)oxy)benzo- [c][1,2,5]thiadiazole (FBTF), and 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-bis(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TTBTTT) were designed, and synthesized successfully via Stille polycondensation reaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and High Resolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclic voltammetry. The electrochemical, and spectroelectrochemical characterization of the polymers were reported in detail. Besides, theoretical calculations were performed to elucidate observed experimental properties. According to the cyclic voltammogram of the polymers, HOMO and LUMO energy levels were calculated as -5.68 eV/-3.91 eV, -5.71 eV/-3.72 eV, -5.61 eV/-4.04 eV, and -5.51 eV/-3.71 eV and the electronic band gaps were 1.77 eV, 1.99 eV, 1.57 eV, and 1.80 eV for PTBTT, PHTBTHT, PFBTF, and PTTBTTT, respectively.
- Karaman, Cansu Zeytun,G?ker, Seza,Hacio?lu, Serife O.,Haciefendio?lu, Tu?ba,Yildirim, Erol,Toppare, Levent
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- Electrochromic properties of pyrene conductive polymers modified by chemical polymerization
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Pyrene is composed of four benzene rings and has a unique planar melting ring structure. Pyrene is the smallest condensed polycyclic aromatic hydrocarbon, and its unique structural properties have been extensively studied. Pyrene has excellent properties such as thermal stability, high fluorescence quantum efficiency and high carrier mobility. This paper mainly used thiophene, EDOT and triphenylamine groups to enhance the pyrene based π-conjugated system and control the molecular accumulation of organic semiconductors, and improve their charge transport performances. Five kinds of polymer were synthesized and correspondingly characterized. The five kinds of pyrene conductive polymer had outstanding properties in terms of solubility, fluorescence intensity and thermal stability, good film-forming properties, stable electrochromic properties and high coloring efficiency. The coloration efficiency (CE) of PPYTP was as high as 277 cm2C?1, and the switching response time was short. The coloring time of PPYEDOT was 1.3 s and the bleaching time was 3.2 s. The lower impedance will also provide the possibility of such polymers being incorporated into electrochromic devices in the future. In short, the synthesized new pyrene conductive polymers will have wide application prospects in the field of electrochromic materials.
- Chang, Lijing,Hou, Yanjun,Li, Rui,Ma, Yang,Miao, Shoulei,Wang, Cheng,Xu, Haoran,Zhang, Yuhang
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p. 39291 - 39305
(2021/12/27)
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- THIOPHENE MONOAMINE BASED ORGANIC-INORGANIC HYBRID PEROVSKITES
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The present disclosure relates to novel thiophene monoamine based organic-inorganic hybrid perovskites, and the method of making and using the novel organic-inorganic hybrid perovskites.
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Paragraph 0071; 0072; 0073
(2020/03/09)
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- A facile synthesis of mesoporous graphitic carbon nitride supported palladium nanoparticles as highly effective and reusable catalysts for Stille coupling reactions under mild conditions
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The development of a Stille coupling protocol that is operable under moderate conditions without using a base is highly required for the synthetic organic chemistry community, which requires an efficient nanocatalyst. In this respect, addressed herein is a facile one-pot synthesis of mesoporous graphitic carbon nitride (mpg-CN) supported Pd NPs, denoted as mpg-CN/Pd hereafter, and investigation of their catalytic activity in Stille cross-coupling reactions for the first time. It has been demonstrated that mpg-CN nanosheets can serve as not only a support material but also a stabilizer for the generation of 4.5 nm Pd NPs. The ecofriendly generated heterogeneous nanocatalyst was characterized by TEM, XRD, XPS, BET surface area and ICP-MS analysis. The mpg-CN/Pd nanocatalysts showed high activity in the Stille coupling reaction of a variety of electron-deficient and electron-rich aryl iodides/bromides and two different organostannanes with a wide substrate scope to afford the corresponding biaryls without using any bases and additional ligands under relatively mild conditions. The catalyst can be easily recovered from the reaction medium by centrifugation. It can be reused at least 5 times without any loss of activity.
- Cetin, Sultan,Kalay, Erbay,Kolemen, Safacan,Metin, ?nder
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p. 6714 - 6723
(2020/05/16)
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- Indole derivative-thiophene compound as well as preparation and application thereof
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The invention provides an indole derivative-thiophene compound as well as preparation and application thereof; the compound takes an indole derivative as a central core and thiophene as a peripheral group, and the structure of the compound is shown as a formula (1). The indole derivative-thiophene compound has the main beneficial effects that (1), the indole derivative-thiophene compound has a reticular space structure and is subjected to electrochemical polymerization to form a film, so that the obtained film has a relatively large specific surface area and also has good electrochemical properties such as electrochromism and the like; and (2), a film prepared by electrochemically taking the compound as a monomer can be randomly switched from yellow to green, the optical contrast ratio is20-50%, the response time is 0.5-9s, and the film shows relatively good spectral electrochemical stability in any wave band and is a potential electrochromic material capable of being used for military camouflage.
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Paragraph 0027-0030
(2020/12/30)
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- Synthesis, Characterization and Photobiological Studies of Ru(II) Dyads Derived from α-Oligothiophene Derivatives of 1,10-Phenanthroline
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Three new bis(2,2′-bipyridine)-heteroleptic Ru(II) dyads incorporating thienyl groups (n?=?1–3, compounds 1, 2 and 3, respectively) appended to 1,10-phenanthroline were synthesized and characterized to investigate the impact of n on the photophysical and photobiological properties within the series. All three complexes showed unstructured emission near 618?nm from a triplet metal-to-ligand charge transfer (3MLCT) state with a lifetime (τem) of approximately 1?μs. Transient absorption measurements revealed an additional excited state that was nonemissive and long-lived (τTA?=?43?μs for 2 and 27?μs for 3), assigned as a triplet intraligand (3IL) state that was accessible only in 2 and 3. All three complexes were strong singlet oxygen (1O2) sensitizers, with quantum yields (Φ?) for 2 and 3 being the largest (74–78%), and all three were photocytotoxic to cancer cells with visible light activation in the order: 3?>?2?>?1. Cell-free DNA photodamage followed the same trend, where potency increased with decreasing 3IL energy. Compounds 2 and 3 also showed in?vitro photobiological effects with red light (625?nm), where their molar absorptivities were ?1?cm?1. These findings highlight that Ru(II) dyads derived from α-oligothiophenes directly appended to 1,10-phenanthroline—namely 2 and 3—possess low-lying 3IL states that are highly photosensitizing, and they may therefore be of interest for photobiological applications such as photodynamic therapy (PDT).
- Monro, Susan,Cameron, Colin G.,Zhu, Xiaolin,Colón, Katsuya L.,Yin, Huimin,Sainuddin, Tariq,Hetu, Marc,Pinto, Mitch,Fuller, Anderson,Bennett, Leah,Roque, John,Sun, Wenfang,McFarland, Sherri A.
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p. 267 - 279
(2018/11/01)
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- Yellow-to-blue switching of indole[3,2-b]carbazole-based electrochromic polymers and the corresponding electrochromic devices with outstanding photopic contrast, fast switching speed, and satisfactory cycling stability
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Three novel π-conjugated indolo[3,2-b]carbazole derivatives, 2,8-di(thiophen-2-yl)-5,11-dioctyl-indolo[3,2-b] carbazole (TICZ), 2,8-bis(4-ethylthiophen-2-yl)-5,11-dioctyl-indolo[3,2-b]carbazole (ETICZ) and 2,8-bis(2-(3,4-ethylenedioxythiophene))-5,11-dioctyl-indolo[3,2-b]carbazole (EDTICZ), were synthesized and electrochemically polymerized to afford the corresponding polymers. The effects of different substituent groups on thiophen units in terms of optical, electrochemical, and electrochromic properties and the performance of electrochromic devices (ECDs) were investigated in detail. Electrochemical and optical analysis demonstrated that incorporation of strong auxochromic groups resulted in polymer PEDTICZ with low oxidation potentials, red-shifted absorption peaks and corresponding narrow band gap values but is unfavorable for incorporating ethyl groups. Spectroelectrochemical studies indicated an evident variation in the absorption spectra as well as significant color changes for all of the polymer films upon application of an external potential. PTICZ had high optical contrast with visible light (58.6%), fast switching speed (0.92 s), and satisfactory coloration efficiency (167 cm2 C?1). Of these three systems, the results for PEDTICZ were next best, and those for PETICZ were third. Also, there was a larger contrast (82.7% and 57.8%) in the NIR region (1500 nm) for the PTICZ and PEDTICZ films, respectively. Along with high coloring efficiencies, these results indicate that these systems are favorable for many NIR applications.
- Xu, Zhen,Zhang, Yuling,Wang, Bozhen,Liu, Zhi,Zhao, Jinsheng,Xie, Yu
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p. 373 - 384
(2019/03/04)
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- Highly fluorescent triazolopyridine-thiophene D-A-D oligomers for efficient pH sensing both in solution and in the solid state
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Conjugated fluorophores have been extensively used for fluorescence sensing of various substances in the field of life processes and environmental science, due to their noninvasiveness, sensitivity, simplicity and rapidity. Most existing conjugated fluorophores exhibit excellent light-emitting performance in dilute solutions, but their properties substantially decrease or even completely vanish due to severe aggregation quenching in the solid state. Herein, we synthesize a series of triazolopyridine-thiophene donor-acceptor-donor (D-A-D) type conjugated molecules with high absolute fluorescence quantum yields (ΦF) ranging from 80% to 89% in solution. These molecules also show unusual light-emitting properties in the solid state with ΦF of up to 26%. We find that owing to the protonation-deprotonation process of the pyridine ring, these compounds display obvious changes in both fluorescence wavelength and intensity upon addition of acids, and these changes can be readily recovered by the successive introduction of bases. By harnessing this phenomenon, we further show that these fluorophores can be employed for efficient and reversible fluorescence sensing of hydrogen ions in a broad pH range (0.0-7.0). With the fabrication of pH testing papers and ink-printed complex patterns including butterflies and letters on substrates, we demonstrate the application of such sensors to fluorescence indication or solid state pH detection for real samples such as volatile acidic/basic gas and water-quality analysis.
- Jian, Nannan,Qu, Kai,Gu, Hua,Zou, Lie,Liu, Ximei,Hu, Faqi,Xu, Jingkun,Yu, Yan,Lu, Baoyang
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p. 7174 - 7182
(2019/04/04)
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- Stannylation of Aryl Halides, Stille Cross-Coupling, and One-Pot, Two-Step Stannylation/Stille Cross-Coupling Reactions under Solvent-Free Conditions
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Solvent-free protocols for palladium-catalyzed stannylation of aryl halides, Stille cross-coupling, and one-pot, two-step stannylation/Stille cross-coupling (SSC) are reported for the first time. (Het)aryl halides bearing acceptor, donor, as well as sterically demanding substituents are stannylated and/or coupled in high yields. The reactions are catalyzed by conventional palladium(II) acetate/PCy3 [Pd(OAc)2/PCy3] under air, using available base CsF, and without the use of high purity reagents. The developed synthetic procedures are versatile, robust, and easily scalable. The absence of solvent, and the elimination of isolation procedures of aryl stannanes makes the SSC protocol simple, step economical, and highly efficient for the synthesis of biaryls in a one-pot two-step procedure.
- Gribanov, Pavel S.,Golenko, Yulia D.,Topchiy, Maxim A.,Minaeva, Lidiya I.,Asachenko, Andrey F.,Nechaev, Mikhail S.
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supporting information
p. 120 - 125
(2018/01/17)
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- Tetraphenylmethane or silane-based compound as well as preparation method and application thereof
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The invention provides a tetraphenylmethane or silane-based compound shown in formula (I), a preparation method of the tetraphenylmethane or silane-based compound and application of the tetraphenylmethane or silane-based compound in synthesizing an electrochromic material membrane as a monomer. As the tetraphenylmethane or silane-based compound has a space structure of tetrahedral tetrad, through membrane formation with electrochemcial polymerization, the obtained membrane expresses larger specific surface area and good electrochemical performance such as electrochromism and the like at the same time. The contrast of the membrane is 30-80 percent, the response time of the membrane is between 0.5s and 6s, the contrast and the response time both express reasonable electrochemcial stable activity, and experimental results show that the material is a potential electrochromic material. The formula of the tetraphenylmethane or silane-based compound is shown in the description.
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Paragraph 0041; 0042; 0043; 0044; 0045; 0046
(2017/10/09)
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- Synthesis of bistriphenylamine- and benzodithiophene-based random conjugated polymers for organic photovoltaic applications
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In this study, donor–acceptor random polymers containing benzotriazole acceptor and bistriphenylamine and benzodithiophene donors, P1 and P2, were successfully synthesized by Stille coupling polymerization. The effect of bistriphenylamine moiety and thiophene π-conjugated linker on electrochemical, spectroelectrochemical, and optical behaviors of the polymers were investigated. Optoelectronic properties and photovoltaic performance of the polymers were examined under the illumination of AM 1.5G, 100 mW?cm?2. The polymers were characterized by cyclic voltammetry, UV-Vis-NIR absorption spectroscopy, gel permeation chromatography. HOMO/LUMO energy levels of P1 and P2 were calculated as ?5.47 eV/–3.41 eV and ?5.43 eV/–3.27 eV, respectively. Bulk heterojunction type solar cells were constructed using blends of the polymers (donor) and [6,6]-phenyl C71 butyric acid methyl ester (PC71BM) (acceptor). Photovoltaic studies showed that the highest power conversion efficiency of these photovoltaic devices were recorded as 3.50% with open circuit voltage; 0.79 V, short circuit current; 9.45 mA?cm?2, fill factor; 0.53 for P1:PC71BM (1:2, w/w) in 3% o-dichlorobenzene (o-DCB) solution and 3.15% with open circuit voltage; 0.75 V, short circuit current; 8.59 mA?cm?2, fill factor; 0.49 for P2:PC71BM (1:2, w/w) in 2% chlorobenzene (CB) solution.
- Cetin, Asli,Istanbulluoglu, Cagla,Hacioglu, Serife Ozdemir,Cevher, Sevki Can,Toppare, Levent,Cirpan, Ali
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p. 3705 - 3715
(2017/09/06)
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- Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction
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Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α, γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.
- Horino, Yoshikazu,Sugata, Miki,Mutsuura, Itaru,Tomohara, Keisuke,Abe, Hitoshi
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supporting information
p. 5968 - 5971
(2017/11/10)
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- METHOD FOR PRODUCING 14 GROUP METAL LITHIUM COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for quantitatively producing a group 14 metal lithium compound under a mild condition. SOLUTION: The method for producing a group 14 metal lithium compound represented by formula (4): R4-nMLin comprises reacting a compound represented by formula (1): R4-nMXn and lithium in the presence of a polycyclic aromatic compound represented by formula (2) or formula (3). [In formula (1) and formula (2), R is a hydrocarbon group; M is a metal atom selected from Si, Ge and Sn; X is a halogen atom or R3M- (R and M are the same as mentioned above); and n is 1 or 2] and [R1 is H or a hydrocarbon group; and m is an integer of 0 to 5.] SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0085; 0087-0088
(2016/10/31)
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- Median alkoxy phenyl substituted and 2, 6 site strong electron donating group substituted BODIPY (4,4'-difluoro-4-bora-3a,4a-diaza-sindacene) derivative and preparation method thereof
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The invention discloses a median alkoxy phenyl substituted and 2, 6 site strong electron donating group substituted BODIPY (4,4'-difluoro-4-bora-3a,4a-diaza-sindacene) derivative and a preparation method thereof. The preparation method comprises: synthesizing a median alkoxy phenyl substituted 2, 6-dibromo fluorine boron intermediate through a series of reactions; and performing Suzuki/Stille coupling reaction by using the intermediate and a variety of modified groups to obtain a median alkoxy phenyl substituted and 2, 6 site thiofuran, thienothiophene, fluorene, carbazole and other strong electron donating units substituted BODIPY derivatives. The absorption spectrum of the prepared target dye molecules generates obvious bathochromic shift, and the maximum absorption wavelength is lengthened to a near infrared area. The median alkoxy phenyl substituted and 2, 6 site strong electron donating group substituted BODIPY derivative has good stability, and has potential application values in the fields of life sciences, solar batteries, environment energy sources and the like.
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Paragraph 0021
(2016/10/10)
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- Design and synthesis of 9,9-dioctyl-9H-fluorene based electrochromic polymers
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Two novel heterocycle-fluorene-heterocycle monomers, 2,2′-(9,9-dioctyl-9H-fluorene-2,7-diyl)dithiophene (Th-F-Th) and 5,5′-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(2,3-dihydrothieno[3,4-b][1,4]dioxine) (EDOT-F-EDOT), were synthesized via Stille coupling reaction and electropolymerized to form corresponding polymers P(Th-F-Th) and P(EDOT-F-EDOT). Furthermore, the optoelectronic properties of the obtained monomers and polymers were explored using cyclic voltammetry (CV), UV-vis, and emission spectra and in situ spectroelectrochemical techniques. The band gap values of monomers calculated by DFT were 3.75 eV for EDOT-F-EDOT and 4.03 eV for Th-F-Th, while that of P(EDOT-F-EDOT) and P(Th-F-Th) were brought down to 1.70 and 2.10 eV, respectively. Both polymers exhibited excellent redox activity and electrochromic performance. P(EDOT-F-EDOT) exhibited a maximum optical contrast of 25.8% at 500 nm in visible region with a response time of 1.2 s. In addition, the coloration efficiency of P(EDOT-F-EDOT) was calculated to be 220 cm2 C-1.
- Jiang, Qinglin,Zhen, Shijie,Mo, Daize,Lin, Kaiwen,Ming, Shouli,Wang, Zhipeng,Liu, Congcong,Xu, Jingkun,Yao, Yuanyuan,Duan, Xuemin,Zhu, Danhua,Shi, Hui
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p. 325 - 334
(2016/01/25)
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- ORGANIC LIGHT COMPOUND AND ORGANIC LIGHT DEVICE USING THE SAME
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PURPOSE: An organic electroluminescent device is provided to provide high luminance efficiency, high luminance, high color purity, and extremely improved life time. CONSTITUTION: An organic electroluminescent comprises a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. The organic layer comprises an organic luminescent compound in chemical formula F1a, F1b, or F2. In the chemical formulas, P1 and P2 is selected from a group consisting of a C5-40 aryl group, a C5-40 heteroaryl group, a C5-40 aryloxy group, a C5-40 arylamino group, C5-40 diarylamino group, C6-40 arylalkyl group, or a group forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, or a fused heteroaromatic ring together with a neighboring group.
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Paragraph 0570-0573
(2020/02/26)
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- Stannyl-Lithium: A Facile and Efficient Synthesis Facilitating Further Applications
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We have developed a highly efficient, practical, polycyclic aromatic hydrocarbon (PAH)-catalyzed synthesis of stannyl lithium (Sn-Li), in which the tin resource (stannyl chloride or distannyl) is rapidly and quantitatively transformed into Sn-Li reagent at room temperature without formation of any (toxic) byproducts. The resulting Sn-Li reagent can be stored at ambient temperature for months and shows high reactivity toward various substrates, with quantitative atom efficiency.
- Wang, Dong-Yu,Wang, Chao,Uchiyama, Masanobu
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supporting information
p. 10488 - 10491
(2015/09/28)
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- Correlation of structure and photovoltaic performance of benzo[1,2-b:4,5-b′]dithiophene copolymers alternating with different acceptors
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Four π-conjugated benzo[1,2-b:4,5-b′]dithiophene (BDT) based polymers were synthesized for application in polymer solar cells. These polymers possessed desirable HOMO/LUMO levels for polymer photovoltaic applications. PBDTT-TTz and PBDTT-DTBT displayed strong absorption in the range of 300-650 nm, while PBDTT-DPP and PBDTT-TTDPP showed a further 100 nm extended absorption band. The lowest unoccupied molecular orbital energy levels of polymers were tuned effectively from -3.34 eV to -3.81 eV by fusing with different accepting units. A maximum power conversion efficiency of 2.60% was obtained from photovoltaic cells with a PBDTT-TTz:PC61BM (1:2, w/w) blend film as the active layer, with a short circuit current density of 8.37 mA cm-2, an open circuit voltage of 0.70 V, and a fill factor of 44.3%. This journal is
- Yu, Jiangsheng,Zhao, Baofeng,Nie, Xuemei,Zhou, Baojin,Li, Yang,Hai, Jiefeng,Zhu, Enwei,Bian, Linyi,Wu, Hongbin,Tang, Weihua
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supporting information
p. 2248 - 2255
(2015/03/18)
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- A Sn atom-economical approach toward arylstannanes: Ni-catalysed stannylation of aryl halides using Bu3SnOMe
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Stannylation of carbon-halogen bonds is one of the most promising and straightforward approaches for the preparation of organostannane compounds. Although a wide variety of methods are now available, all protocols require the use of highly nucleophilic organometals or wasteful stannyl sources like distannanes. Here, we report a new nickel-catalysed stannylation of aryl and alkenyl-halides using Bu3SnOMe as a stannyl source to afford aryl and vinyl-stannanes, respectively. This method enables the stannylation of not only bromides, but also chlorides and triflates to furnish functionalized aryl- and alkenyl-stannanes without the release of wasteful and toxic stannyl byproducts.
- Komeyama, Kimihiro,Asakura, Ryota,Takaki, Ken
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supporting information
p. 8713 - 8716
(2015/08/24)
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- Efficient one-pot cross-coupling of two aryl halides by stannylation/stille reaction in water under microwave irradiation
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A simple and highly efficient one-pot approach has been developed for the Pd(PPh3)4-catalyzed cross-coupling of two different aryl or heteroaryl bromides/iodides. This method involves the combined use of microwave irradiation and water as a single solvent to achieve sequential stannylation and Stille cross-coupling reactions, which allows rapid access to a wide variety of biaryls in good to high yields. Furthermore, utilizing this step-economical protocol, 2,5-dibromopyridine was iteratively diarylated and the Boscalid intermediate was also synthesized in a one-pot manner. Copyright
- Tan, Xin,Zhou, Zi Jie,Zhang, Jia Xin,Duan, Xin Hong
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supporting information
p. 5153 - 5157
(2014/09/29)
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- Electrochromic properties of multicolored novel polymer synthesized via combination of benzotriazole and N-functionalized 2,5-di(2-thienyl)-1H-pyrrole units
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Synthesis of new conducting polymers is desired since their electrochemical and optical properties enable them to be used as active layers in many device applications. Benzotriazole and N-functionalized 2,5-di(2-thienyl)-1H-pyrrole (SNS Series) containing polymers showed very promising results as electrochromic materials. In order to observe the effect of the combination of these two units, three new monomers; 2-(6-(2,5-bis(5-methylthiophen-2-yl)-1H-pyrrol-1-yl) hexyl)-4,7-di(thiophen-2-yl)-2H benzo[d][1,2,3]triazole (M1), 2-(6-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)hexyl)-4,7-di(thiophen-2-yl) -2H-benzo[d][1,2,3]triazole (M2) and 2-(6-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl) hexyl)-4,7-bis(5-methylthiophen-2-yl)-2H-benzo[d][1,2,3]triazole (M3) were synthesized. To better characterize the electronic and spectroscopic properties of the monomers, density functional theory (DFT) and its time-dependent generalization (TD-DFT) were used to calculate their vertical ionization potentials, vertical electron affinity and to simulate and interpret their infrared and UV-vis spectra. The monomers were electrochemically polymerized and the resultant polymers were characterized with cyclic voltammetry and UV-vis-NIR spectroscopy techniques. An electrochromic device was constructed with electrochemical polymer of M2. The device switched between red and blue colors and showed exceptional optical memory.
- Rende, Eda,Kilic, Cihan E.,Udum, Yasemin Arslan,Toffoli, Daniele,Toppare, Levent
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p. 454 - 463
(2014/08/18)
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- Sonochemical synthesis of bis(tri-n-butylstannyl) aromatic compounds via Barbier-like reactions
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This paper reports a study of the synthesis of aryltri-n-butylstannanes via a sonochemical Barbier reaction of aryl- and heteroaryl bromides with bis(tri-n-butyltin) oxide (2) in THF. Our results demonstrate that, despite previous reports on contrary, the aryltributylstannanes can also be obtained under the same reaction conditions via sonicated reactions between aryl monobromides and tri-nbutyltin chloride (2). A comparative study of the reactions of electrophiles 2 and 3 with bromobenzene, 2-bromopyridin, o- and m-bromoanisole, m-bromotoluene, 9-bromophenthrene, and 9-bromoanthracene, indicates that the corresponding aryl- and heteroaryl-tri-n-butylstannyl derivatives are obtained in about the sameyields. Best reaction conditions and the results obtained in the investigation of the sonicated reactions between several aromatic and heteroaromatic dibromides are also reported. It was found that the reactions using 1,2-, 1,3-, and 1,4-dibromobenzenes, 4,40-dibromobiphenyl, 1,4-dibromonaphthalene, 2,5-and 3,5-dibromopyridines, and 2,5-dibromothiophene lead to the corresponding bis(tri-n-butylstannylated) derivatives in many cases in very high yields. Also the excellent results obtained in the sonicated reactions of 1,3,5-tribromobenzene with 2 and 3 are reported.
- Gerbino, Darío C.,Fidelibus, Pablo M.,Mandolesi, Sandra D.,Ocampo, Romina A.,Scoccia, Jimena,Podestá, Julio C.
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- An A-D-A small molecule based on the 3,6-dithienylcarbazole electron donor (D) unit and nitrophenyl acrylonitrile electron acceptor (A) units for solution processed organic solar cells
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A new A-D-A small molecule (SM) based on a 3,6-dithienylcarbazole donor unit at the center and nitrophenyl acrylonitrile acceptor units as the terminal ends was synthesized by the Pd catalyzed Stille coupling reaction for application as a donor material in the organic bulk heterojunction solar cells. The SM possesses a low lying HOMO energy level at -5.34 eV and optical band gap of 1.74 eV. The photovoltaic performance of the SM was investigated with PC 60BM and PC70BM as acceptors cast from THF with 3% CN additive and without additive. The power conversion efficiency (PCE) of the organic solar cells based on SM:PC60BM cast from THF solvent reached 1.94% with a high Voc of 0.94 V, a Jsc of 6.08 mA cm -2 and FF of 0.34, where as the PCE of SM:PC70BM cast from THF solvent was 2.65% with a Voc of 0.96 V, a Jsc of 7.26 mA cm-2 and FF of 0.38%, under the illumination intensity of 100 mW cm-2. The higher PCE of the organic solar cells based on PC 70BM as an electron acceptor has been attributed to its strong absorption in the visible region than PC60BM. The PCE of the organic solar cells has been further improved to 3.76% and 4.96% for SM:PC 60BM and SM:PC70BM, respectively, cast with CN-THF solvent. The Royal Society of Chemistry 2013.
- Singh, Manjeet,Kurchania, Rajnish,Mikroyannidis,Sharma,Sharma
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p. 2297 - 2306
(2013/07/05)
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- D-π-A-π-D type benzothiadiazole-triphenylamine based small molecules containing cyano on the π-bridge for solution-processed organic solar cells with high open-circuit voltage
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Two novel D-π-A-π-D structured small molecules composed of benzothiadiazole and triphenylamine were designed and synthesized. BDCTBT with cyano on the π-bridge exhibited a deep HOMO energy level, resulting in an impressive VOC of up to 1.04 V with a PCE of 3.85%, while non-cyano substituted BDETBT yielded a VOC of 0.94 V and a PCE of 1.99%.
- Zeng, Shaohang,Yin, Lunxiang,Ji, Changyan,Jiang, Xueying,Li, Kechang,Li, Yanqin,Wang, Yue
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supporting information
p. 10627 - 10629
(2012/11/07)
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- QUINOID THIOPHENE ORGANIC PHOTOELECTRIC MATERIAL, PREPARATION METHOD THEREOF AND APPLICATION THEREOF
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Quinoid thiophene organic photoelectric material with formula (1), method for its preparation and application thereof are provided, wherein R1, R2, R3, R4, R5 and R6, which are identical or different, represent H, C1?C30 alkyl or alkoxy, m and n, which are identical or different, represent integers between 1 and 20. The quinoid thiophene organic photoelectric material with formula (1) has wide spectral response, good thermal stability and environmental stability.
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Page/Page column 5
(2012/12/13)
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- Facile synthesis and characterization of a novel thiophene-fused polycyclic aromatics based on pyrene
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A novel large thiophene-fused polycyclic aromatics 1 based on pyrene 5 has been synthesized, and its structure was confirmed by 1H NMR, 13C NMR, MS, UV-vis and elemental analysis. The key steps of the synthesis involved the Stille cross-coupling reaction and followed by selective β-β oxidative cyclization of pendant thienyl rings by FeCl3 under mild conditions.
- Duan, Zong Fan,Yang, Zhi Gang,Liu, Dong Jie,Cai, Li,Hoshino, Daiki,Morita, Tsuyoshi,Zhao, Gao Yang,Nishioka, Yasushiro
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scheme or table
p. 819 - 822
(2012/01/05)
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- A novel dye-dopant, a composition comprising the same and a photovoltaic device including such composition
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Disclosed herein are a novel dye-dopant, a composition comprising the same and a photovoltaic device producing from such composition. An organic polymeric thin film produced from the composition comprising the dye-dopant may enhance the photo-voltaic converting efficiency of a solar device comprising the same under Air Mass (A.M.) 1.5 Global solar conditions.
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Page/Page column 8-9
(2011/06/26)
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- Effect of conjugated core building block dibenzo[a,c]phenazine unit on π-conjugated electrochromic polymers: Red-shifted absorption
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A comparative investigation was undertaken for the electrosynthesis and electrochemical properties of three different electroactive polymers having a conjugated core building block, dibenzo[a,c]phenazine. A series of monomers has been synthesized as regards to thiophene based units; thiophene, 3-hexyl thiophene, and 3,4-ethylenedioxythiophene. The effects of different donor substituents on the polymers' electrochemical properties were examined by cyclic voltammetry. Introducing highly electron-donating (ethylene dioxy) group to the monomer enables solubility while also lowering the oxidation potential. The planarity of the monomer unit enhances π-stacking and consequently lowering the Eg from 2.4 eV (PHTP) to 1.7 (PTBP). Cyclic voltammetry and spectroelectrochemical measurements revealed that 2,7-bis(4-hexylthiophen-2-yl) dibenzo[a,c]phenazine (HTP) and 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5- yl)dibenzo[a,c]phenazine (TBP) possessed electrochromic behavior. The colorimetry analysis revealed that while PTBP have a color change from red to blue, PHTP has yellow color at neutral state and blue color at oxidized state. Hence the presence of the phenazine derivative as the acceptor unit causes a red shift in the polymers' absorption to have a blue color.
- Unver, Elif Kose,Tarkuc, Simge,Udum, Yasemin Arslan,Tanyeli, Cihangir,Toppare, Levent
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experimental part
p. 1714 - 1720
(2011/03/22)
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- Acid secretion inhibitor
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The present invention provides a compound having a superior acid secretion inhibitory effect and showing an antiulcer activity and the like. The present invention provides a compound represented by the formula (I) wherein R1 is a nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle, the nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle optionally has substituent(s), R2 is an optionally substituted C6-14 aryl group, an optionally substituted thienyl group or an optionally substituted pyridyl group, R3 and R4 are each a hydrogen atom, or one of R3 and R4 is a hydrogen atom and the other is an optionally substituted lower alkyl group, an acyl group, a halogen atom, a cyano group or a nitro group, and R5 is an alkyl group or a salt thereof.
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Page/Page column 52
(2008/06/13)
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- THE CHEMISTRY OF ORGANOLEAD(IV) TRICARBOXYLATES. SYNTHESIS AND ELECTROPHILIC HETEROARYLATION REACTIONS OF 2- AND 3-THIENYL-, AND 2- AND 3-FURYL-LEAD
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Tin(IV)-lead(IV) exchange and mercury(II)-lead(IV) exchange reactions have been used to obtain 2-thienyl-lead triacetate (3), 2-thienyl-lead tribenzoate (4), 3-thienyl-lead triacetate (16), 2-furyl-lead triacetate (21), and 3-furyl-lead triacetate (31).In reactions with the β-dicarbonyl compounds (7), (11), and (13), the above heteroaryl-lead compounds behaved as 2-thienyl, 3-thienyl, 2-furyl, and 3-furyl cation equivalents respectively, giving the α-heteroaryl β-dicarbonyl compounds (8), (12), (14), (17), (18), (19), (25), (27), (28), (38), (34), and (35) in synthetically useful yields.
- Pinhey, John T.,Roche, Eric G.
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p. 2415 - 2422
(2007/10/02)
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