- Synthesis and photovoltaic properties of low-bandgap 4,7-dithien-2-yl-2,1, 3-benzothiadiazole-based poly(heteroarylenevinylene)s
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Three novel low-bandgap copolymers containing alkylated 4,7-dithien-2-yl-2,1,3-benzothiadiazole (HBT) and different electron-rich functional groups (dialkylfluorene (PFV-HBT), dialkyloxyphenylene (PPV-HBT) and dialkylthiophene (PTV-HBT)) were prepared by Horner polycondensation reactions and characterized by 1H NMR, gel permeation chromatography, and elemental analysis. The alkyl side chain brings these polymeric materials good solubility in common organic solvents, which is critical for the manufacture of solar cells in a cost-effective manner. The copolymers exhibit low optical bandgap from 1.48 to 1.83 eV. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of the copolymers were measured by cyclic voltammetry. Theoretical calculations revealed that the variation laws of HOMO and the LUMO energy levels are well consistent with cyclic voltammetry measurement. The bulk heterojunction photovoltaic devices with the structure of ITO/PEDOT-PSS/polymer:PCBM/LiF/Al were fabricated by using the three copolymers as the donor and (6,6)-phenyl-C61-butyric acid methyl ester (PCBM) as the acceptor in the active layer. The device based on PTV-HBT:PCBM (1:4 w/w) achieved a power conversion efficiency of 1.05% under the illumination of AM 1.5, 100 mW/cm2.
- Wen, Shanpeng,Pei, Jianing,Li, Pengfei,Zhou, Yinhua,Cheng, Weidong,Dong, Qingfeng,Li, Zaifang,Tian, Wenjing
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- Physical, mechanical, and conductivity properties of poly(3-hexylthiophene) -montmorillonite clay nanocomposites produced by the solvent casting method
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Polymer nanocomposites (PNCs) of poly(3-hexylthiophene) (P3HT) with organically modified montmorillonite (om-MMT) clay have been prepared by the solvent casting method. WAXS and TEM studies indicate exfoliated clay structure for lower clay content, but at higher clay content (5%, w/w) intercalated structures appear. The interchain lamella of P3HT exists in the nanocomposite, and the P3HT crystals become more ordered, showing better X-ray diffraction peaks. The thermal stability of PNCs increases significantly, and 1% clay content PNC exhibits the maximum thermal stability. The glass transition temperature (Tg), β-transition temperature (Tβ), the melting point (Tm), and the enthalpy of fusion (ΔT) of the PNCs are increased as compared to those of pure P3HT. The storage modulus (G′) of PNCs showed a dramatic increase from that of pure P3HT, and the increase is larger in the temperature range 20-50 °C. The FTIR study indicates a decrease in Si-O-Si and Si-O stretching frequency for the exfoliated clay structure. The UV-vis study showed a blue shift of the π-π*transition band of P3HT in the PNCs, and they exhibit photoluminescence quenching which increases with increase in clay concentration. The dc conductivity of undoped PNCs remains almost the same as that of pure P3HT, but iodine-doped PNCs, however, exhibit 2.5-3 times greater conductivity than that of iodine-doped P3HT.
- Kuila, Biplab K.,Nandi, Arun K.
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- Regiospecific Synthesis of 3-Alkylfuranes and 3-Alkylthiophenes via Organoboranes
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The reaction of bromide or iodide with ate-complexes obtained from trialkylboranes and 3-lithiofuran or 3-lithiothiophene gives the corresponding 3-alkylfurans or 3-alkylthiophenes in good yields, respectively.
- Akimoto, Itaru,Sano, Masahiro,Suzuki, Akira
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- Redox-Divergent Construction of (Dihydro)thiophenes with DMSO
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Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.
- Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang
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supporting information
p. 24284 - 24291
(2021/10/08)
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- Efficient Pd-Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents
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Organolithium compounds are amongst the most important organometallic reagents and frequently used in difficult metallation reactions. However, their direct use in the formation of C?C bonds is less established. Although remarkable advances in the coupling of aryllithium compounds have been achieved, Csp2?Csp3 coupling reactions are very limited. Herein, we report the first general protocol for the coupling or aryl chlorides with alkyllithium reagents. Palladium catalysts based on ylide-substituted phosphines (YPhos) were found to be excellently suited for this transformation giving high selectivities at room temperature with a variety of aryl chlorides without the need for an additional transmetallation reagent. This is demonstrated in gram-scale synthesis including building blocks for materials chemistry and pharmaceutical industry. Furthermore, the direct coupling of aryllithiums as well as Grignard reagents with aryl chlorides was also easily accomplished at room temperature.
- Dilchert, Katharina,Gessner, Viktoria H.,Gro?johann, Angela,Rodstein, Ilja,Scherpf, Thorsten,Steinert, Henning,Tappen, Jens
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supporting information
p. 20596 - 20603
(2020/09/09)
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- 1,2,3-Triazolyl functionalized thiophene, carbazole and fluorene based A-: Alt -B type π-conjugated copolymers for the sensitive and selective detection of aqueous and vapor phase nitroaromatics (NACs)
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A series of highly emissive π-conjugated A-alt-B type copolymers (P1-P3) appended with a 1,2,3-triazole moiety was synthesized via Suzuki polymerization. The well-defined and soluble π-conjugated copolymers were characterized via multinuclear NMR spectroscopy and tetradetector GPC studies, showing a molecular weight (Mn) in the range of 16.4-20.1 kDa with a polydispersity index in the range of 1.25-1.42. The synthesized emissive π-conjugated polymer probes were explored as fluorescent chemosensors for nitroaromatic compounds (NACs) in solution, vapor and contact mode. Detailed photophysical and sensing studies were performed to understand the polymer-NAC interaction, inducing the selective fluorescence quenching of the π-conjugated polymer probes through the photoinduced electron transfer (PET) mechanism. All the polymeric probes (P1-P3) were highly reversible in nature with NACs, and thus could be reused multiple times. The limit of detection of the probes towards nitroaromatics was found to be in the range of 120-200 ppb with a high association constant in the order of 104 M-1. Furthermore, test paper kits were also fabricated, which allowed the trace detection of picric acid by the naked eye, making it a practical means for the quick, easy and inexpensive on-site detection of NAC-based explosives.
- Giri, Dipanjan,Patra, Sanjib K.
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supporting information
p. 14469 - 14480
(2020/11/09)
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- Conductive triethylene glycol monomethyl ether substituted polythiophenes with high stability in the doped state
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Synthesis of two conducting polymers containing 3-hexylthiophene and 3-[2-(2-(2-methoxyethoxy)ethoxy)ethoxy]thiophene is demonstrated. In thin-film transistors, the high-molecular-weight polymer shows an average mobility of 4.2 × 10?4 cm2 V?1 s?1. Most importantly, the polymers have high conductivity upon doping with iodine and also have high stability in the doped state with high conductivities measured even after 1 month. Furthermore, the doping causes transparency to thin films of the polymer and the films are resistant to common organic solvents. All these properties indicate a great potential for the iodine-doped polymer to be used as an alternative to commercially available poly(3,4-ethylenedioxythiophene):poly(styrene sulfonate).
- Dissanayake, Dushanthi S.,Gunathilake, Samodha S.,Udamulle Gedara, Chinthaka M.,Du, Jia,Yoo, Sang Ha,Lee, Youngmin,Wang, Qing,Gomez, Enrique D.,Biewer, Michael C.,Stefan, Mihaela C.
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p. 1079 - 1086
(2019/03/21)
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- The Discovery of Citral-Like Thiophenes in Fried Chicken
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The isomers of 3,7-dimethyl-2,6-octadienal, more commonly known together as citral, are two of the most notable natural compounds in the flavor and fragrance industry. However, both isomers are inherently unstable, limiting their potential use in various applications. To identify molecules in nature that can impart the fresh lemon character of citral while demonstrating stability under acidic and thermal conditions has been a major challenge and goal for the flavor and fragrance industry. In the study of fried chicken, several alkyl thiophenecarbaldehydes were identified by gas chromatography-mass spectrometry and gas chromatography-olfactometry that provided a similar citral-like aroma. The potential mechanism of formation in fried chicken is discussed. Furthermore, in order to explore the organoleptic properties of this structural backbone, a total of 35 thiophenecarbaldehyde derivatives were synthesized or purchased for evaluation by odor and taste. Certain organoleptic trends were observed as the length of the alkyl or alkenyl chain increased or when the chain was moved to different positions on the thiophene backbone. The 3-substituted alkyl thiophenecarbaldehydes, specifically 3-butyl-2-thiophenecarbaldehyde and 3-(3-methylbut-2-en-1-yl)-2-thiophenecarbaldehyde, exhibited strong citrus and citral-like notes. Several alkyl thiophenecarbaldehydes were tested in high acid stability trials (4 °C vs 38 °C) and outperformed citral both in terms of maintaining freshness over time and minimizing off-notes. Additional measurements were completed to calculate the odor thresholds for a select group of thiophenecarbaldehydes, which were found to be between 4.7-215.0 ng/L in air.
- Cannon, Robert J.,Curto, Nicole L.,Esposito, Cynthia M.,Payne, Richard K.,Janczuk, Adam J.,Agyemang, David O.,Cai, Tingwei,Tang, Xiao-Qing,Chen, Michael Z.
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p. 5690 - 5699
(2017/07/24)
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- Syntheses and photovoltaic properties of 6-(2-thienyl)-4H-thieno[3,2-b]indole based conjugated polymers containing fluorinated benzothiadiazole
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In this report, a series of copolymers based on 6-(2-thienyl)-4H-thieno[3,2-b]indole (TTI) as an electron-rich unit and fluorinated DTBT as an electron-deficient unit were synthesized, namely PTTIF1 and PTTIF2, and applied to photovoltaic devices. TTI unit was coupled with fluorinated DTBT to utilize the merit of introduction of fluorine atom leading to the lowering of the HOMO energy level while keeping high planarity of the conjugated backbone. The synthesized copolymers show a noticeable change in HOMO energy levels as compared with non-fluorinated polymer (PTTIDTBT-h). Optimized photovoltaic devices of PTTIF2 exhibited power conversion efficiency of 4.36% with decent JSC and FF values, which can be explained by the higher charge transporting ability of PTTIF2 with preferable face-on crystallite population than PTTIF1 in grazing incident wide-angle X-ray scattering (GIWAXS).
- Jeong, Ina,Chae, Sangmin,Yi, Ahra,Kim, Juae,Chun, Ho Hwan,Cho, Jung Hyeong,Kim, Hyo Jung,Suh, Hongsuk
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p. 115 - 125
(2016/12/30)
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- Cobalt-Catalyzed Reductive Alkylation of Heteroaryl Bromides: One-Pot Access to Alkylthiophenes, -furans, -selenophenes, and -pyrroles
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A practical and convenient Co-catalyzed alkylation method for the facile introduction of various alkyl chains into organic electronically significant heteroaryl compounds, including thiophenes, furans, selenophenes, and pyrroles, is reported. Under well-optimized reaction conditions, a wide range of alkylated heteroaryl compounds have beeen efficiently prepared in moderate to good isolated yields. Notably, 2- or 3-alkylthiophenes, which play a decisive role in polymer chemistry and organic materials, have been synthesized step-economically for the first time by this reductive-coupling methodology using inexpensive cobalt salts as catalysts. This straightforward synthetic procedure avoids the preparation of moisture-unstable organometallic reagents (RMgX or RZnX) required in conventional alkylation protocols. Various alkyl chains have been introduced into organic, electronically important heteroaryl compounds step-economically through Co-catalyzed reductive alkylation reactions. The resulting alkylheteroarenes are indispensable building blocks for polymer chemistry and π-functional organic materials.
- Cai, Deng-Jhou,Lin, Po-Han,Liu, Ching-Yuan
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supporting information
p. 5448 - 5452
(2015/08/24)
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- Synthesis of poly(thiophene-alt-pyrrole) from a difunctionalized thienylpyrrole by Kumada polycondensation
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A difunctional thienylpyrrole monomer with a bromide on the thienyl moiety and a magnesium halide on the pyrrole moiety was prepared via chemo-selective magnesium-iodine exchange. Based on this monomer, a π-conjugated alternating poly(thiophene-alt-pyrrole) PTP was synthesized via nickel and palladium catalyzed Kumada polycondensation. The optical and thermal properties of this polymer have been investigated and suggested a wide band gap polymer, with a very low Tg for such polymers.
- He, Lu-Ying,Urrego-Riveros, Sara,Gates, Paul J.,N?ther, Christian,Brinkmann, Maren,Abetz, Volker,Staubitz, Anne
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supporting information
p. 5399 - 5406
(2015/07/15)
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- Modulating crystallinity of poly(3-hexylthiophene) via microphase separation of poly(3-hexylthiophene)-polyisoprene block copolymers
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A series of poly(3-hexylthiophene)-block-polyisoprene (P3HT-b-PI) diblock copolymers (DBCP) and polyisoprene-block-poly(3-hexylthiophene)-block-polyisoprene (PI-b-P3HT-b-PI) triblock copolymers (TBCP) with accurately controlled molecular architecture were synthesized via highly efficient coupling reaction between aldehyde end-functionalized P3HT and living anionic polyisoprene. The self-assembly behaviors, considering morphology and crystallinity, of the thermal annealed bulk samples of these DBCPs and TBCPs containing various PI content were systematically investigated. The DBCPs behaved very differently from most published P3HT BCP systems, showing elongated fibers with preserved crystallinity regardless of the PI fraction. More noteworthy, with PI fraction less than 40 wt %, the DBCPs exhibited parallel straight fibers longer than several micrometers accompanied by concurrent enhanced crystallinity. The unique microstructure of the DBCPs might originate from moderate microphase separation between P3HT and PI as well as high flexibility of PI to conduct the packing of P3HT. The TBCPs, by contrast, exhibited highly curved interdomain boundaries with significant depressed crystallinity, resembling P3HT diblock copolymers in the strong phase segregation regime, as more pronounced entanglement of the two terminal PI segments would restrict the movement of P3HT.
- Lim, Herman,Chao, Chi-Yang,Su, Wei-Fang
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p. 3269 - 3281
(2015/06/08)
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- Structural design of benzo[1,2- b:4,5- b ′]dithiophene-based 2D conjugated polymers with bithienyl and terthienyl substituents toward photovoltaic applications
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In this contribution, six conjugated polymers consisting of benzo[1,2-b:4,5-b′]dithiophene-bithiophene (BDT-BT) and benzo[1,2-b:4,5-b′]dithiophene-benzothiadiazle (BDT-BTD) as building blocks in the main chain were synthesized by coupling polymerization and utilized for photovoltaic applications. By directly attaching three kinds of alkylthienyl side chains to the conjugated main chain, the resulted two-dimensional configuration revealed a broader absorption range due to the ground state electron transition of their corresponding alkylthienyl units and polymer backbone. Temperature-dependent absorbance, emission spectra, and thermal annealing further verify that the shoulder band(s) were originated from the aggregated (crystalline) species of polymers. The photovoltaic properties of the donor-acceptor polymers revealed well-defined side chain geometries, physical, and electronic structures and showed the highest power conversion efficiency of 4.25% among polymer solar cells based on two-dimensional (2-D) bithienyl- or terthienyl-substituted benzodithiophene.
- Kuo, Cheng-Yu,Nie, Wanyi,Tsai, Hsinhan,Yen, Hung-Ju,Mohite, Adytia D.,Gupta, Gautam,Dattelbaum, Andrew M.,William, Darrick J.,Cha, Kitty C.,Yang, Yang,Wang, Leeyih,Wang, Hsing-Lin
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p. 1008 - 1020
(2014/03/21)
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- Influence of the bulkiness of the substituent on the aggregation and magnetic properties of poly(3-alkylthiophene)s
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A series of poly(3-alkylthiophene)s (P3ATs) (P1-P5) has been synthesized via a Ni(dppp)-mediated polymerization, varying the bulkiness of the alkyl side chains in order to investigate the influence of the bulkiness of the alkyl substituent on the aggregation and magnetic properties of P3ATs. UV-Vis spectroscopy, performed in solution as well as in film, shows that the stacking of the polymers becomes more complicated as the bulkiness of the side chains increases. Both the π-interactions and the planarization of the polymer chains are diminished. While aggregation is absent in poor solvent for the polymer with the most bulky side chains, aggregation was present in film, albeit slowed down. This behavior was also confirmed by X-ray diffraction (XRD) and differential scanning calorimetry (DSC) experiments. Electron spin resonance (ESR) measurements, performed at 300 K on powders, confirmed the trend of decreasing supramolecular order with increasing bulkiness of the side-chain. Magnetization measurements, performed at 5 and 300 K, are in line with our hypothesis on the influence of π-interactions and the fraction of planar polymer chains on the coercivity and saturation magnetization, respectively.
- Peeters, Helmuth,Jivanescu, Mihaela,Stesmans, Andre,Pereira, Lino M. C.,Dillemans, Leander,Locquet, Jean-Pierre,Van Bael, Margriet J.,Persoons, Andre,Koeckelberghs, Guy
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- An efficient and reliable procedure for the preparation of highly reactive Rieke zinc
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Rieke zinc has a wide potential for applications in organic chemistry, notably for the synthesis of highly chemoselective organozinc reagents. However, due to the rather unreliable preparation method, leading to large batch to batch variations, its use has been rather limited. Rieke zinc is commonly prepared by the reduction of zinc chloride with lithium using a stoichiometric amount of naphthalene. In our hands, it was observed that the reaction outcome was highly dependent on the naphthalene source and purity grade. The presence of benzothiophene seems crucial to avoid coagulation of the zinc particles and the amount of benzothiophene has a large effect on the physical properties and the reactivity of the resulting zinc powder. Accordingly, highly reactive Rieke zinc was easily prepared from zinc chloride by adding an optimum amount (3 mol% with regard to ZnCl2) of benzothiophene into the lithium naphthalenide solution (prepared in situ). The Rieke zinc obtained in this way was successfully employed in the so-called "Rieke method" to prepare regioregular poly(3-hexylthiophene) (P3HT). The novel approach enables preparation of Rieke zinc in a reproducible manner, which considerably facilitates its use in both small molecule and polymer synthesis.
- Kudret, Suleyman,D'Haen, Jan,Lutsen, Laurence,Vanderzande, Dirk,Maes, Wouter
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p. 569 - 575
(2013/05/09)
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- Transition between triangular and square tiling patterns in liquid-crystalline honeycombs formed by tetrathiophene-based bolaamphiphiles
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A series of 5,5′′′-diphenyl tetrathiophenes with polar glycerol groups at each end and two lateral flexible chains self-assemble into a series of liquid-crystalline honeycombs, formed by the π-conjugated rods which enclose polygonal prismatic cells filled by the lateral chains. With increasing chain length a discontinuous transition from triangular to square honeycombs takes place. At this transition a periodic honeycomb composed of a mixture of square and triangular cells in a ratio 1:2 was formed at low temperature, whereas at higher temperature a hexagonal columnar phase composed of triangular and randomly distributed rhombic cells, a new kind of cybotactic nematic phase, and also a cybotactic isotropic phase, both composed of square honeycomb fragments, represent the intermediate states. This provides an example of a dynamic self-assembled system where, depending on the molecular mobility, the transition between two periodic structures with different symmetry either leads to an increase of complexity, or to a chaotic regime with reduced order.
- Cheng, Xiaohong,Gao, Hongfei,Tan, Xiaoping,Yang, Xueyan,Prehm, Marko,Ebert, Helgard,Tschierske, Carsten
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p. 3317 - 3331
(2013/07/26)
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- Synthesis and photovoltaic properties of polythiophene incorporating with 3,4-difluorothiophene units
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Two polythiophene derivatives using fluorine atoms and hexyl or hexyloxy group as electron-withdrawing and donating substituents have been synthesized. The introduction of fluorine atoms to the polythiophene backbones simultaneously lowers the HOMO and narrows the bandgap, and the stronger electron-donating ability of hexyloxy side chain further reduces the bandgap. As a result, poly[3-hexylthiophene-2,5-diyl-alt-3,4-difluorothiophene] (PHTDFT) shows HOMO and bandgap of -5.31/1.83 eV and poly[3,4-dihexyloxythiophene-2,5-diyl-alt-3,4- difluorothiophene] (PDHOTDFT) shows HOMO and bandgap of -5.14/1.68 eV, both are lower than -4.76/2.02 eV of P3HT. Benefiting from the lower HOMO, PHTDFT:PC 61BM (1:1) polymer solar cells obtain a power conversion efficiency of 1.11% and an impressed open-circuit voltage of 0.79 V under solar illumination AM1.5 (100 mW/cm2). Two new polythiophene derivatives incorporating with 3,4-difluorothiphene units, PHTDFT and PDHOTDFT, show lower HOMO and narrower bandgap than that of P3HT. Benefiting from the lower HOMO, PHTDFT:PC61BM (1:1) polymer solar cells obtain a power conversion efficiency of 1.11% and an impressed open-circuit voltage of 0.79 V under solar illumination AM1.5 (100 mW/cm2). Copyright
- Huang, Linquan,Yang, Dong,Gao, Qiang,Liu, Yan,Lu, Shengmei,Zhang, Jian,Li, Can
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p. 1385 - 1390
(2013/12/04)
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- Effect of side-chain architecture on the optical and crystalline properties of two-dimensional polythiophenes
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The present study reported here synthesis of three novel two-dimensional (2D) polythiophene derivatives with conjugated terthiophene-vinylene side chain - poly{3-(5″-hexyl-2,2′:5′,2″-terthiophenyl-5-vinyl) thiophene-alt-thiophene} (P1), poly{3-(5,5″-dihexyl-2,2′:5′, 2″-terthiophenyl-3′-vinyl)thiophene-alt-thiophene} (P2), and poly{3-(4,4″-dihexyl-2,2:5′,2″-terthiophene-3′-vinyl) thiophene-alt-thiophene} (P3) - that were synthesized via stille coupling reaction. The terthiophene side chain with different conformations conjugated to the polythiophene main chain via vinyl linkage provided the ability to control the molecular organization, hence affecting the optoelectronic and electrochemical properties of 2D polymers. TD-DFT calculation with the B3LYP/6-31+g(d) function on electronic structures of the monomers was consistent with the experimental results. It suggested that the energetic states of HOMO and LUMO were highly dependent on the side-chain architectures. These polythiophene thin films fabricated by spin-casting show a broader absorption ranges from 300 to 700 nm which was significantly wider than the absorption of pure poly(3-hexylthiophene). When comparing the solid-state absorption spectra of these polymers before and after thermal annealing, P3 displayed the most red-shift in the wavelength range between 450 and 700 nm. It was presumably due to an extended conjugation length resulting from the linear conformation and preferred chain packing, as manifested in the X-ray diffraction. Molecular dynamics (MD) simulation on polymers with different side chains in isolated and packed states suggests planar conformation of the main chain was adopted and regulated by the side chains which were placed in parallel with the main-chain direction. Interestingly, P1 solution revealed an excitation-dependent emission property, suggesting a structural inhomogeneity in solution. Contrary to P1, the PL spectra of P2 and P3 showed only one emission peak at 460 nm, regardless of the excitation energy. Orientation and regiochemistry of the terthiophene side chain had a major impact on the overall optical and electronic properties of the polymer. Moreover, the HOMO and LUMO of these three polymers had been determined through cyclic voltammetry. HOMO of the three polymers were in the following order: P1 > P2 > P3. It implied that the energy level was regiochemistry dependent and directly associated with the linked position between backbone and conjugated side chain. Most importantly, through mesogen-jacketed-like design strategy employed in the present study, the improved packing of these two-dimensional polymers offered insights into structure design to enhance properties that have strong ties to the electronic devices.
- Kuo, Cheng-Yu,Huang, Yu-Chen,Hsiow, Chuen-Yo,Yang, Yu-Wen,Huang, Ching-I,Rwei, Syang-Peng,Wang, Hsing-Lin,Wang, Leeyih
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p. 5985 - 5997
(2013/09/02)
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- Dual selectivity: Electrophile and nucleophile selective cross-coupling reactions on a single aromatic substrate
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The development of a high yielding, both nucleophile and electrophile selective cross-coupling reaction with aromatic rings is presented. The reaction is general with respect to functional groups. Furthermore, the products still contain a boronic ester and a bromide. These two functional groups allow them to be easy-to-prepare, highly complex starting materials for further reactions, avoiding protecting group transformations.
- Heinrich, Annika C. J.,Thiedemann, Birk,Gates, Paul J.,Staubitz, Anne
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supporting information
p. 4666 - 4669
(2013/10/08)
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- Synthesis and mesophase behavior of phenylthiophene based amphiphilic molecules
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Novel amphiphilic molecules consisting of a rigid 2-phenylthiophene core, with a polar flexible tri(oxylethylene) moiety attached to the phenyl ring and one or two alkyl chains attached to the thiophene ring at the other side have been synthesized by using Ni(II) and Pd(0) catalyzed coupling reaction as key steps. The tri(oxylethylene) moieties were terminated with hydroxyl group, sodium carboxylate group and lithium carboxylate group respectively. The thermotropic and solvent induced liquid crystalline behavior of these substances was investigated by polarized optical microscopy, differential scanning calorimetry and X-ray diffraction. Thereby the influence of the terminal groups attached to the tri(oxylethylene) moities as well as the influence of the length and the number of the alkyl chains on the mesophase behavior were investigated. The single alkyl chain Na-carboxylate termianted derivatives show smectic A phases, double alkyl chain Na-carboxylate terminated derivatives show a thermo tropic hexagonal columnar mesophase, while columnar mesophases are found in both single and double alkyl chain Li-carbonate terminated derivatives. The model for molecular organization in the hexagonal columnar mesophase is established.
- Jing, Shan,Zhang, Ruilin,Dai, Heng,Du, Chao,Cheng, Xiaohong
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scheme or table
p. 577 - 584
(2012/06/04)
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- Photovoltaic devices using semiconducting polymers containing head-to-tail-structured bithiophene, pyrene, and benzothiadiazole derivatives
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An alternating copolymer composed of heal-to-tail-structured 3,4'-dihexyl-2,2'-bithiophene (DHBT) and pyrene units [poly(DHBT-alt-PYR)] was synthesized using a Stille coupling reaction for use in photovoltaic devices as a p-type donor. For the reduction of the bandgap energy of poly(DHBT-alt-PYR), 4,7-bis(3'-hexyl-2,2'-bithiophen-5-yl)benzo[c][1,2,5]thiadiazole (BHBTBT) units were introduced into the polymer. Poly(DHBT-co-PYR-co-BHBTBT)s were synthesized using the same polymerization reaction. The synthesized polymers were soluble in common organic solvents and formed smooth thin films after spin casting. The optical bandgap energies of the polymers were obtained from the onset absorption wavelengths. The measured optical bandgap energy of poly(DHBT-alt-PYR) was 2.47 eV. As the BHBTBT content in the ter-polymers increased, the optical bandgap energies of the resulting polymers decreased. The bandgap energies of poly(50DHBT-co-40PYR-co-10BHBTBT) and poly(50DHBT-co-20PYR-co-30BHBTBT) were 1.84 and 1.73 eV, respectively. Photovoltaic devices were fabricated with a typical sandwich structure of ITO/PEDOT:PSS/active layer/LiF/Al using the polymers as electron donors and [6,6]-phenyl C71-butyric acid methyl ester as the electron acceptor. The device using poly(50DHBT-co-20PYR-co- 30BHBTBT) showed the best performance among the fabricated devices, with an open-circuit voltage, short-circuit current, fill factor, and maximum power conversion efficiency of 0.68 V, 5.54 mA/cm2, 0.35, and 1.31%, respectively.
- Kim, Ji-Hoon,Lee, Sunyoung,Kang, In-Nam,Park, Moo-Jin,Hwang, Do-Hoon
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scheme or table
p. 3415 - 3424
(2012/08/29)
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- Synthesis of a new conjugated polymer composed of pyrene and bithiophene units for organic solar cells
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An alternating conjugated copolymer composed of pyrene and bithiophene units, poly(DHBT-alt-PYR) has been synthesized. The synthesized polymer was found to exhibit good solution processibility and thermal stability, losing less than 5% of their weight on heating to approximately 370 °C. The synthesized polymer showed its maximum absorption and peak PL emission at 401 and 548 nm, respectively. The optical band gap energy of the polymer was determined by absorption onset to be 2.64 eV. Highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of the polymer was determined to be-5.48 and-2.84 eV by cyclic voltametry (CV) and the optical band gap. The polymer photovoltaic devices were fabricated with a typical sandwich structure of ITO/PEDOT:PSS/active layer/LiF/Al using poly(DHBT-alt-PYR) as an electron donor and C60-PCBM or C70-PCBM as electron acceptors. The open circuit voltage, short circuit current and fill factor of the device using C70-PCBM as an acceptor were 0.75 V, 3.80 mA/cm 2 and 0.28, respectively, and the maximum power conversion efficiency of the device was 0.80%. Copyright
- Lee, Sun-Young,Jung, Choong-Hwa,Kang, Jun,Kim, Hee-Joon,Shin, Won Suk,Yoon, Sung Cheol,Moon, Sang-Jin,Lee, Changjin,Hwang, Do-Hoon
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p. 4367 - 4372
(2012/06/16)
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- POLYMERS COMPRISING 3 -SUBSTITUTED THIOPHENE MOIETIES AS ACTIVE LAYERS FOR SOLAR CELLS
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The invention relates to new monomers and polymers as well as blends of such polymers with an electron acceptor. The invention also relates to a blend for use in a photovoltaic device, comprising: (a) a polymer comprising monomer units according to the formula (I), wherein L' is selected from the group consisting of L-C(O)O-J, L-C(O)NR'-J, L-OCO-J', L-NR'CO-J', L-SCO-J', L-O-J, L-S-J, L-Se-J, L-NR'-J and L-CN wherein L is a linear or branched alkylene group having from 1 to 10 carbon atoms, wherein J is a hydrogen atom or a linear or branched alkyl group having from 1 to 4 carbon atoms, wherein J' is a group having from 1 to 10 carbon atoms, being saturated or unsaturated, linear or branched, comprising a phenyl unit or not comprising a phenyl unit, wherein R' is a hydrogen atom or a linear or branched alkyl group having from 1 to 4 carbon atoms, and (b) an electron acceptor such as a fullerene derivative.
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Page/Page column 28-29
(2011/06/26)
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- Cross-linked conjugated polymer fibrils: Robust nanowires from functional polythiophene diblock copolymers
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A series of poly(3-hexyl thiophene) (P3HT)-based diblock copolymers were prepared and examined in solution for their assembly into fibrils, and post-assembly cross-linking into robust nanowire structures. P3HT-b-poly(3-methanol thiophene) (P3MT), and P3HT-b-poly(3-aminopropyloxymethyl thiophene) (P3AmT) diblock copolymers were synthesized using Grignard metathesis (GRIM) polymerization. Fibrils formed from solution assembly of these copolymers are thus decorated with hydroxyl and amine functionality, and cross-linking is achieved by reaction of diisocyanates with the hydroxyl and amine groups. A variety of cross-linked structures, characterized by transmission electron microscopy (TEM), were produced by this method, including dense fibrillar sheets, fibril bundles, or predominately individual fibrils, depending on the chosen reaction conditions. In solution, the cross-linked fibrils maintained their characteristic vibronic structure in solvents that would normally disrupt (dissolve) the structures.
- Hammer, Brenton A. G.,Bokel, Felicia A.,Hayward, Ryan C.,Emrick, Todd
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experimental part
p. 4250 - 4256
(2012/04/10)
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- Hierarchical helical assembly of conjugated poly(3-hexylthiophene)-block- poly(3-triethylene glycol thiophene) diblock copolymers
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We report on the solution-state assembly of all-conjugated polythiophene diblock copolymers containing nonpolar (hexyl) and polar (triethylene glycol) side chains. The polar substituents provide a large contrast in solubility, enabling formation of stably suspended crystalline fibrils even under very poor solvent conditions for the poly(3-hexylthiophene) block. For appropriate block ratios, complexation of the triethylene glycol side chains with added potassium ions drives the formation of helical nanowires that further bundle into superhelical structures.
- Lee, Eunji,Hammer, Brenton,Kim, Jung-Keun,Page, Zachariah,Emrick, Todd,Hayward, Ryan C.
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supporting information; experimental part
p. 10390 - 10393
(2011/09/13)
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- Controlling blend film morphology by varying alkyl side chain in highly coplanar donor-acceptor copolymers for photovoltaic application
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A series of varied length alkyl substituted donor-acceptor (D-A) conjugated copolymers with benzo[1,2-b:4,5-b′]dithiophene (BDT) as donor and thiophene rings attached to both sides of the benzothiadiazole (TBT) moieties as acceptors were designed and synthesized. The optical and electrochemical properties showed that the absorption spectrum, the band gaps, and the energy levels of the copolymers were not affected by the varied substituted alkyls, and all these copolymers showed low band gaps around 1.75 eV. In addition, the morphologies of the blend film between copolymers and PCBM can be fine-tuned by increasing the length of substituted alkyl of the copolymers, changing from pea-like aggregation to interpenetrating network to grain-like aggregation. Bulk heterojunction photovoltaic devices were fabricated by using the copolymers as donors and (6,6)-phenyl C61-butyric acid methyl ester (PC 61BM) or (6,6)-phenyl C71-butyric acid methyl ester (PC71BM) as acceptors. The optimized photovoltaic performances showed the stable open-circuit voltage (Voc) in the range of 0.68 to 0.74 eV, and dramatically increasing short circuit current density (Jsc) by optimizing the blending morphologies of copolymer and PCBM films. The optimized photovoltaic performance with a Voc of 0.70 V, J sc of 7.19 mA/cm2, a fill factor (FF) of 0.52, and a power conversion efficiency (PCE) of 2.88%, was obtained by the copolymer PBDT-TBT-C8 (PBDT-TBT-C8:PC61BM, 1:3 w/w, in CB solution). This is due to its low band gap and interpenetrating network morphology of PBDT-TBT-C8:PC 61BM blend film. The photovoltaic device based on PBDT-TBT-C8:PC 71BM showed a Jsc of 8.6 mA/cm2 and a PCE of 3.15%.
- Li, Yaowen,Chen, Yujin,Liu, Xing,Wang, Zhong,Yang, Xiaoming,Tu, Yingfeng,Zhu, Xiulin
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scheme or table
p. 6370 - 6381
(2012/06/18)
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- A selective and direct synthesis of 2-bromo-4-alkylthiophenes: Convenient and straightforward approaches for the synthesis of head-to-tail (HT) and tail-to-tail (TT) dihexyl-2,2′-bithiophenes
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A straightforward method for the synthesis of 2-bromo-4-alkylthiophenes was developed, and the desired products were obtained in the highest chemical yields (>90%) reported to date. 2-Bromo-4-alkylthiophenes were synthesized by regioselective lithiating of 3-alkylthiophenes with n-BuLi and quenching with bromine at -78°C. Moreover, a simple and efficient protocol for the synthesis of dihexyl-2,2′-bithiophenes was developed by employing 2-bromo-4-hexylthiophene instead of the commonly used monomer, 2-bromo-3-hexylthiophene. Kumada and Suzuki cross-coupling reactions were conducted to synthesize the desired products as head-to-tail (HT) and tail-to-tail (TT) regioisomers in high yields and excellent selectivity.
- El-Shehawy, Ashraf A.,Abdo, Nabiha I.,El-Barbary, Ahmed A.,Lee, Jae-Suk
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supporting information; scheme or table
p. 4526 - 4529
(2010/10/02)
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- POLYMERISABLE COMPOUNDS FOR MAKING OPTO-ELECTRONIC DEVICES
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This invention provides monomeric compounds represented by the structural formula (I) or the structural formula (II) which can be polymerized into crosslinkable polymers useful for producing opto-electronic devices.
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Page/Page column 25-26
(2010/04/03)
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- Base-catalyzed halogen dance reaction and oxidative coupling sequence as a convenient method for the preparation of dihalo-bisheteroarenes
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Figure presented A one-pot preparation of the 2,2′-dibromo-1, 1′-bisheteroarenes 3a-d from bromo-heteroarenes utilizing the sequence of the base-catalyzed halogen dance (BCHD) reaction and CuCl2-promoted oxidative coupling of the in situ formed α-lithio-β-halo-heteroarenes 2a-d provides a convenient access to precursors for the preparation of tricyclic heteroaromatic cores. The structures of 3a,b,d, 6, and 9 were confirmed by single-crystal X-ray analysis, and dibromides 3a and 3b were used for the preparation of dithieno-[2,3-b:3′,2′-d]-pyrrole 10a and its selenophene analogue 10b, respectively.
- Getmanenko, Yulia A.,Tongwa, Paul,Timofeeva, Tatiana V.,Marder, Seth R.
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supporting information; experimental part
p. 2136 - 2139
(2010/08/05)
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- Synthesis and characterization of donor-acceptor poly(3-hexylthiophene) copolymers presenting 1,3,4-oxadiazole units and their application to photovoltaic cells
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We have used Grignard metathesis polymerization to prepare poly(3-hexylthiophene)-based copolymers containing electron-withdrawing 4-tert-butyl phenyl-1,3,4-oxadiazole-phenyl moieties as side chains. We characterized these copolymers using 1H and 13C nuclear magnetic resonance spectroscopy, thermogravimetric analysis, and gel permeation chromatography. The band gap energy of copolymer was determined from the onset of the optical absorption. The quenching effects were observed in the photoluminescence spectra of the copolymers incorporating pendant electron-deficient 1,3,4-oxadiazole moieties on the side chains. The photocurrents of devices were enhanced in the presence of an optimal amount of the 1,3,4-oxadiazole moieties, thereby leading to improved power conversion efficiencies.
- Wang, Hsu-Shen,Su, Ming-Shin,Wei, Kung-Hwa
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scheme or table
p. 3331 - 3339
(2011/04/25)
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- Process for the preparation of substituted heteroaromatics
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A process is described for the preparation of substituted heteroaromatics of the general formula (I) where X is oxygen, sulphur or NR5 where R5 is hydrogen, C1-C20-alkyl or C5-C6-aryl and R4 is C1-C20-alkyl, C5-C6-aryl or heteroaryl, R1, R2, R3 is hydrogen, halogen, C1-C20-alkyl, C5-C6-aryl or heteroaryl, by reaction A) of a halogenated heteroaromatic of the general formula (II) where X has the meaning given for formula (I) and R6 is bromine, iodine or chlorine and R1, R2 and R3 have the meaning given for formula (I), with a Grignard reagent of the general formula (III) [in-line-formulae]R4MgHal??(III)[/in-line-formulae]whereR4 has the meaning given for formula (I) andHal is bromine, iodine or chlorine orB) reaction of the halogenated heteroaromatics of the formula (II) with magnesium firstly to give a Grignard compound of the general formula (IIIa) where Hal is bromine, iodine or chlorine and X and R1, R2 and R3 have the meaning given for formula (I), and further reaction with a halogenated compound of the general formula (IV) [in-line-formulae]R4Hal??(IV)[/in-line-formulae]whereR4 has the meaning given for formula (I) andHal is bromine, iodine or chlorine,where the reactions A) or B) are in each case carried out in the presence of an Ni or Pd catalyst, characterized in that the process is carried out in the presence of cycloalkyl alkyl ether as solvent and optionally a further solvent. Likewise described is the use of cycloalkyl alkyl ethers, in particular cyclopentyl methyl ether, in the Kumada reaction for the preparation of substituted heteroaromatics, in particular substituted thiophenes.
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Page/Page column 5
(2010/09/05)
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- Liquid-crystalline triangle honeycomb formed by a dithiophene-based X-shaped bolaamphiphile
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Soft supramolecular triangles: The molecule shown displays a new liquid-crystalline phase formed by a periodic array of triangular cylinders. The cylinders are fused to form a honeycomb by hydrogen-bonding networks running along the vertices, and the cells are filled by molten alkyl chains. The thickness of the walls separating the compartments is equal to the width of the π-conjugated rods.
- Cheng, Xiaohong,Dong, Xing,Wei, Guanghui,Prehm, Marko,Tschierske, Carsten
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supporting information; scheme or table
p. 8014 - 8017
(2010/02/27)
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- Towards a general solid phase approach for the iterative synthesis of conjugated oligomers using a germanium based linker - First solid phase synthesis of an oligo-(triarylamine)
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The development of a germanium-based linker system for the solid phase synthesis (SPS) of 3-(n-hexyl)thiophene oligomers and the first SPS of triarylamine oligomers via iterative chain extension is described. The efficiency of the key steps in the oligomer syntheses and their compatibility with the germanium linker are demonstrated by the SPS of bi-[3-(n-hexyl) thiophene] 19 and ter-(triarylamine) 50. The use of a germanium-based linker in combination with appropriately selected silicon-based blocking/protecting groups allows double coupling to drive the key cross coupling steps to completion hence minimising deletion sequences and also allows for traceless and potentially functionalisative cleavage from the resin. The latter feature has yet to be fully explored but towards this end the first ipso-borodegermylation reaction of a 2-germyl-3-(n-hexyl)thiophene is presented. The Royal Society of Chemistry.
- Turner, David J.,Anemian, Remi,MacKie, Philip R.,Cupertino, Domenico C.,Yeates, Stephen G.,Turner, Michael L.,Spivey, Alan C.
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p. 1752 - 1763
(2008/02/10)
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- Preparation of regioregular alkylthiophene oligomers and their optical properties
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We successfully prepared regioregular hexylthiophene oligomers, dimmer to seximer of hexylthiophene, by using the Suzuki coupling. Introduction of hexyl chain provided excellent solubility to the oligothiophenes; even in seximer, the oligomer was soluble in conventional organic solvents such as toluene and chloroform. Additionally, the oligomer formed thin film with good uniformity by spin-coating from chloroform solution. In this article, we also report optical properties of the oligomer.
- Gondo, Schoichi,Goto, Yasuyuki,Era, Masanao
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p. 353 - 358
(2008/03/12)
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- Process for the kumada coupling reaction
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A method for the formation of 3-alkylthiophenes or 3-arylthiophenes from 3-halothiophenes. More particularly, improvements on the Kumada coupling reaction for the production of 3-alkylthiophenes or 3-arylthiophenes by reacting a 3-halothiophene with an alkylmagnesiumhalide or arylmagnesiumhalide Grignard reagent in the presence of a catalyst and a 2-methyl tetrahydrofuran solvent. The 2-methyl tetrahydrofuran solvent allows for higher concentrations of the Grignard reagent with minimal or no dithienyl side product generation, achieving higher product yields and at a lower cost than other known methods.
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Page/Page column 3
(2008/06/13)
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- Head-to-tail regioregular oligothiophene-functionalized 9,9′-spirobifluorene derivatives. 1. Synthesis
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Two series of novel fully conjugated oligomers, oligothiophene-functionalized 9,9′-spirobifluorene derivatives, have been developed in this contribution. First, four 9,9′-spirobifluorene bromide derivatives (compounds 1a-d) are prepared through various synthetic routes. Oligothiophene derivatives with or without substituents are synthesized through the Grignard and Suzuki coupling reactions. The Negishi coupling reactions between oligothienylzinc chloride and various 9,9′spirobifluorene bromides with Pd(PPh3)4 as catalyst successfully produce the desired compounds, unsubstituted oligothiophene-functionalized 9,9′-spirobifluorene derivatives, compounds 2 to 4ad. Since the Negishi coupling reactions afford regioregularly head-to-tail (H-T) oligo(4-nhexylthiophene)-functionalized 9,9′-spirobifluorene derivatives in poor yields, the Suzuki coupling reactions between sodium 4-n-hexylthienyl-2-boronate 8, and various 9,9′-spirobifluorene-based bromides 1a-d and 9-16 are employed to produce highly regioregular head-to-tail oligothiophenefunctionalized 9,9′-spirobifluorene derivatives (compounds 5 to 7a-d) in very high yields. We also investigate the effect of solvents on the Suzuki coupling reactions. The structure and purity of all compounds are verified by FT-IR, 1H and 13C NMR, MS, and elemental analysis.
- Pei, Jian,Ni, Jing,Zhou, Xing-Hua,Cao, Xiao-Yu,Lai, Yee-Hing
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p. 4924 - 4936
(2007/10/03)
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- New and efficient access to 3-substituted 2,5-dibromothiophenes. Consecutive nickel-catalyzed electrochemical conversion to thienylzinc species
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We have achieved the stepwise synthesis of 3-substituted thienylzinc reagents using both electrochemical methods and an original bromination procedure. For several compounds 3-bromothiophene was the starting substrate, which was functionalized according to recently developed electrochemical procedures. The nickel-catalyzed electrochemical reduction of the resulting 3-substituted 2,5-dibromothiophenes in the presence of zinc salts allowed the formation of monothienylzinc species in good yields. The selectivity of this reaction is discussed within the context of the electrochemical synthesis of regioregular polythiophenes.
- Mellah,Labbe,Nedelec,Perichon
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p. 318 - 321
(2007/10/03)
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- Synthesis and Properties of Dihexylbithienoquinonoid Derivatives with Head-to-head, Head-to-tail, and Tail-to-tail Orientations
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2,2′-(Dihexyl-2,2′-bithienylidene-5,5′-diylidene) bis(propanedinitrile)s (dihexylbithienoquinonoid derivatives), in which two 3-hexylthiophene moieties are connected with head-to-tail (HT) and tail-to-tail (TT) orientations, were synthesized. HT bithienoquinonoid was isolated in a single form together with a small amount of its bromo derivative, similarly to the case for the head-to-head (HH) orientational isomer. On the other hand, TT isomer exhibited a peculiar feature in solution, affording an equilibrium mixture of two geometrical isomers. Electronic and electrochemical properties of these bithienoquinonoids were studied and compared with those of HH isomer. The results proved that all these bithienoquinonoid compounds possess highly polarizable and electron-acceptable properties. HH bithienoquinonoid was reduced through one two-electron transfer process, while HT and TT isomers were reduced through two one-electron transfer processes via stable radical anions to the corresponding dianions.
- Higuchi, Hiroyuki,Yoshida, Shima,Uraki, Yoshiyuki,Ojima, Juro
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p. 2229 - 2237
(2007/10/03)
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- Syntheses and Properties of Unsymmetrically Substituted Bi- and Ouaterthiophenes
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The unsymmetrically substituted bi- and quaterthiophene derivatives were synthesized. The unsymmetrically substituted bithiophenes carrying the electron-withdrawing substituent X on one of the outer thiophene rings exhibited the maxima of absorption bands at the longer wavelengths than the symmetrically disubstituted bithiophene derivatives, while the unsymmetrical quaterthiophenes had such maxima at the shorter wavelengths than the corresponding symmetrical ones. The trend of bathochromic shift of the longest wavelength absorption bands due to the electron-withdrawing substituent X was more pronounced in case of bi- or quaterthiophenes bearing push-pull substituents. The unsymmetrical quaterthiophenes exhibited the greater third-order nonlinear optical (TNLO) properties than the corresponding bithiophenes, similarly to the case between the symmetrical bi- and quaterthiophenes. However, the TNLO properties of the unsymmetrical biand quaterthiophenes showed no dependence on the electron-withdrawing strength of the substituent X, unlike those of the symmetrical ones.
- Higuchi, Hiroyuki,Uraki, Yoshiyuki,Yokota, Hiroki,Koyama, Haruki,Ojima, Juro,Wada, Tatsuo,Sasabe, Hiroyuki
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p. 483 - 495
(2007/10/03)
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- Synthesis of substituted oligothiophenes and X-ray crystal structures of 3′-methyl-2,2′:5′,2″-terthiophene, 3,3″-dimethyl-2,2′:5′,2″-terthiophene and 5′-(2-thienyl)-2,2′:3′,2″-terthiophene
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A range of substituted oligothiophenes has been prepared and characterised. Crystal structures were determined for three substituted terthiophenes. Both in solution and in the solid state, syn-conformers were found to be populated to a greater extent than expected.
- Chaloner, Penny A.,Gunatunga, Sumudu R.,Hitchcock, Peter B.
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p. 1597 - 1604
(2007/10/03)
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- Synthesis and Properties of α,ω-Disubstituted Oligo(3-hexylthiophene)s and Oligothienoquinonoids in Head-to-head Orientation
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The two types of Highly-ordered oligo(3-hexylthiophene)s in head-to-head orientation, a series od α,ω-disubstituted oligothiophenes and a series of bis(dicyanomethylene)oligothienoquinonoids, were synthesized.The properties of these compounds are discussed on the basis of the electronic spectra and cyclic voltammetry.
- Higuchi, Hiroyuki,Nakayama, Taketoshi,Koyama, Haruki,Ojima, Juro,Wada, Tatsuo,Sasabe, Hiroyuki
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p. 2363 - 2378
(2007/10/03)
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- A CONVENIENT SYNTHESIS OF 3-ALKYLTHIOPHENES
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The known procedures for the synthesis of 3-alkylthiophenes are rather lengthy or involved.By using the NiDPPP++ catalyzed cross-coupling method between 3-bromothiophene and Grignard reagents derived from alkyl halides a number of 3-alkylthiophenes have been prepared in a one-step reaction in good to excellent yields.
- Pham, Chiem Van,Mark, Harry B.,Zimmer, Hans
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p. 689 - 696
(2007/10/02)
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