- 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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- Synthesis and fine-tuning the pore properties of a thiophene based porous organic framework by post-oxidation treatment
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Porous organic frameworks (POFs) are an important class of materials, which have attracted great interests in recent years. The post modification of porous organic frameworks provides an efficient way to fine tune the properties of POFs for specific applications. However, most of the post functionalization methods need harsh reaction conditions and specific reagents and lead to a notable pore width decrease, which hinder the pore accessibility. Herein, we designed and synthesized a thiophene based POF with high surface area and stability. A straightforward post-oxidation of thiophene based POFs by meta-chloroperbenzoic acid introduced sulfone groups as hydrogen bonding sites in the channel with a less effected pore width in a controllable manner. The hydrogen bond acceptor sulfone groups could promote the adsorption of ammonia and enhance the proton conductivity of phosphoric acid or imidazole infiltrated POFs. The proton conductivity of phosphoric acid doped oxidized thiophene based POFs is over 10-3 S cm-1 at 120 °C under anhydrous conditions, which could be a promising candidate for fuel cells.
- Liu, Yanze,Zuo, Yiming,Li, Shuai,Li, Jiani,Li, Li,Liu, Caixia,Ashraf, Shumalia,Li, Pengfei,Wang, Bo
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supporting information
p. 21953 - 21958
(2019/10/11)
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- Rapid release from near-infrared polymer loaded liposomes for photothermal and chemo-combined therapy
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PEGylated liposomal doxorubicin is a polymeric antitumor drug approved clinically by the Food and Drug Administration, but it has no essentially increasing efficacy compared to free doxorubicin (DOX) because of the slow release rate. In this paper, a near-infrared polymer was designed and encapsulated in liposomes to photothermally accelerate the release of DOX. This polymer loaded liposome provides a maximum absorption that covers the ideal phototherapeutic window between 800 and 850 nm, which ensures an efficient photothermal release of DOX as a nano drug for the delivery of photothermal and chemo-combined therapy in a highly efficient cancer treatment.
- Li, Dehua,Zhang, Meiduo,Yao, Jingke,Zhang, Zhe
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supporting information
p. 2274 - 2277
(2019/02/05)
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- ORGANIC SEMICONDUCTOR COMPOUND HAVING LOW BAND-GAP, AND TRANSISTOR AND ELECTRONIC DEVICE INCLUDING THE SAME
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Provided is an organic semiconductor compound comprising a structural unit represented by chemical formula (1). The definition of each substituent in chemical formula (1) is the same as that defined in the specification.(AA) Current density [mA/cm^2](BB) Voltage [V]COPYRIGHT KIPO 2018
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Paragraph 0178; 0191-0197
(2018/05/03)
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- COMPOUND, COMPOSITION, ORGANIC SEMICONDUCTOR DEVICE, AND METHOD FOR PRODUCING COMPOUND
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PROBLEM TO BE SOLVED: To provide a compound, a composition, an organic semiconductor device and a method for producing a compound which make it possible to reduce an absolute value of threshold voltage without reducing carrier mobility. SOLUTION: The present invention provides a compound represented by formula (1) (X is Se or Te). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0100-0101
(2018/02/21)
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- Efficient deep-red electroluminescent donor-acceptor copolymers based on 6,7-dichloroquinoxaline
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Since the large steric hindrance caused by chlorine atoms not only suppresses the aggregation but also results in large stokes shift and low self-absorption, a series of donor-acceptor alternating copolymers based on 6,7-dichloroquinoxaline have been synthesized by modifying the structures of oligothiophenes. All the polymers have been well characterized to study the effects of the length of oligothiophenes and the steric hindrance on the optical, electronic and electroluminescent properties. It was observed that the intramolecular charge transfer absorption was weakened by steric hindrance. Unlike non-chloride analogues, prolonged conjugated length resulted in smaller bandgap, given similar steric hindrance. Deep-red emission centered at 678?nm with brightness about 1800?cd?m?2 was achieved with external quantum efficiency 1.34% using dopant/host technic.
- Gao, Xiang,Zhang, Yubao,Fang, Cheng,Cai, Xiang,Hu, Bin,Tu, Guoli
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p. 276 - 282
(2017/05/10)
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- Novel 4,8-benzobisthiazole copolymers and their field-effect transistor and photovoltaic applications
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A series of copolymers containing the benzo[1,2-d:4,5-d′]bis(thiazole) (BBT) unit has been designed and synthesised with bisthienyl-diketopyrrolopyrrole (DPP), dithienopyrrole (DTP), benzothiadiazole (BT), benzodithiophene (BDT) or 4,4′-dialkoxybithiazole (BTz) comonomers. The resulting polymers possess a conjugation pathway that is orthogonal to the more usual substitution pathway through the 2,6-positions of the BBT unit, facilitating intramolecular non-covalent interactions between strategically placed heteroatoms of neighbouring monomer units. Such interactions enable a control over the degree of planarity through altering their number and strength, in turn allowing for tuning of the band gap. The resulting 4,8-BBT materials gave enhanced mobility in p-type organic field-effect transistors of up to 2.16 × 10-2 cm2 V-1 s-1 for pDPP2ThBBT and good solar cell performance of up to 4.45% power conversion efficiency for pBT2ThBBT.
- Conboy, Gary,Taylor, Rupert G. D.,Findlay, Neil J.,Kanibolotsky, Alexander L.,Inigo, Anto R.,Ghosh, Sanjay S.,Ebenhoch, Bernd,Krishnan Jagadamma, Lethy,Thalluri, Gopala Krishna V. V.,Sajjad, Muhammad T.,Samuel, Ifor D. W.,Skabara, Peter J.
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supporting information
p. 11927 - 11936
(2017/11/30)
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- Rodlike Tetracene Derivatives
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Efficient and versatile synthetic access to rodlike tetracene derivatives was developed by means of Diels–Alder cycloaddition, halogenation, halogen–metal exchange, and transition metal mediated coupling reactions. Herein, the synthesis and structural, electrical, and charge-transport properties of three of the resulting materials, namely, 2-(tetracen-2-yl)tetracene, 1,4-bis(2-tetracenyl)benzene, and 2,5-bis(2-tetracenyl)thiophene, are presented. Good crystallization behavior on SiO2 substrates, narrowing of the bandgap by 0.2 eV, and a decrease of the ionization potential of more than 0.5 eV compared to tetracene were observed. Charge-carrier field-effect mobilities on the order of 10?1 cm2 V?1 s?1, on/off ratios of 105, and threshold voltages Vth15 V were found in thin-film organic field-effect transistors prepared by standard high-vacuum deposition techniques.
- Roth, Michael,Ahles, Marcus,Gawrisch, Christian,Schwalm, Thorsten,Schmechel, Roland,Melzer, Christian,von Seggern, Heinz,Rehahn, Matthias
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p. 13445 - 1345
(2017/09/14)
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- Indolo[3,2-b]carbazole structure unit-containing piezochromic material and application thereof
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The invention discloses an indolo[3,2-b]carbazole structure unit-containing piezochromic material. The piezochromic material has a structural formula shown in the description; and in the description, R represents a hydrogen atom, a methyl group, an ethyl group or an isopropyl group, n represents 1, 2 or 3, and Ar represents one of groups also shown in the description. The invention also discloses an application of the indolo[3,2-b]carbazole structure unit-containing piezochromic material in electroluminescent devices. The piezochromic material has the advantages of no toxicity, simple preparation technology, low cost and excellent piezochromic performance.
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Paragraph 0035
(2017/08/30)
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- Effect of substituent groups on quinoxaline-based random copolymers on the optoelectronic and photovoltaic properties
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In this study, three low band gap donor-acceptor (D-A) type quinoxaline-based random copolymers were synthesized. The effect of varying substituent groups on quinoxaline groups on optoelectronic properties and the performance of bulk-heterojunction polyme
- Cevher, Sevki Can,Hizalan, Gonul,Temiz, Cansel,Udum, Yasemin Arslan,Toppare, Levent,Cirpan, Ali
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p. 208 - 216
(2016/09/07)
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- Synthesis and photovoltaic properties of low bandgap dimeric perylene diimide based non-fullerene acceptors
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Non-fullerene organic acceptors have attracted increasing attention in recent years. One of the challenges in the synthesis of non-fullerene organic acceptors is to tune the absorption spectrum and molecular frontier orbitals, affording low bandgap molecules with improved absorption of the near-infrared solar photons. In this paper, we present the synthesis, optoelectronic and photovoltaic properties of a series of dimeric perylene diimide (PDI) based non-fullerene acceptors. These PDI dimers are bridged by oligothiophene (T) from 1T to 6T. With the increase of the oligothienyl size, the highest occupied molecular orbital (HOMO) energy is raised from -5.65 to -5.10 eV, while that of the lowest unoccupied molecular orbit (LUMO) is kept constant at -3.84 eV, affording narrow bandgap from 1.81 to 1.26 eV. The absorption from the oligothiophene occurs between 350 and 500 nm, which is complementary to that from its bridged PDI units, leading to a wide spectral coverage from 350 to 850 nm. The optimal dihedral angle between the bridged two perylene planes is dependent on the oligothienyl size, varying from 5° to 30°. The solubility of the dimers depends on the oligothienyl size and can be tuned by the alkyl chains on the bridged thienyl units. The possible applications as the solution-processable non-fullerene organic acceptor is primarily studied using commercial P3HT as the blend donor. The photovoltaic results indicate that 1T, 4T and 6T all yield a higher efficiency of ~1.2%, whereas 2T, 3T and 5T all give a lower efficiency of 0.5%. The difference in the cell performance is related with the tradeoff between the differences of absorption, HOMO level and film-morphology between these dimers.
- Zhang, Xin,Yao, Jiannian,Zhan, Chuanlang
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p. 209 - 217
(2016/02/18)
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- UNIMOLECULAR AND ORGANIC SOLAR CELL COMPRISING THE SAME
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Provided are a single molecule and an organic solar cell including the single molecule. Specifically, the single molecule has an end represented by chemical formula 1 and includes at least two units selected from the group consisting of units represented by chemical formula 2, wherein the two units are the same or different from each other.COPYRIGHT KIPO 2015
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Paragraph 0458-0461
(2016/10/09)
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- Preparation of near-infrared absorbing composites comprised of conjugated macroligands on the surface of PbS nanoparticles
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We report a facile macroligand strategy towards the synthesis of low-bandgap inorganic-organic composites comprised of semiconductor PbS nanoparticles and functional copolymers. For this, thiol-functional thiophene-based macroligands have been used as coligands for PbS nanoparticles. Thus, solution processable organic-inorganic hybrid materials with absorption in the near-infrared have been obtained. The resulting nanoparticle-polymer composites were characterized in detail by optical and FT-IR spectroscopy as well as TEM showing their potential as novel functional inorganic-organic hybrid materials when applied in initial proof-of-concept hybrid photovoltaic devices.
- Zhang, Jinming,Bahrig, Lydia,Puetz, Andreas,Kanelidis, Ioannis,Lenkeit, Daniel,Pelz, Simon,Hickey, Stephen G.,Klein, Michael F.G.,Colsmann, Alexander,Lemmer, Uli,Eychmüller, Alexander,Holder, Elisabeth
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p. 5525 - 5533
(2013/10/21)
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- All-polymer solar cells with 3.3% efficiency based on naphthalene diimide-selenophene copolymer acceptor
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The lack of suitable acceptor (n-type) polymers has limited the photocurrent and efficiency of polymer/polymer bulk heterojunction (BHJ) solar cells. Here, we report an evaluation of three naphthalene diimide (NDI) copolymers as electron acceptors in BHJ solar cells which finds that all-polymer solar cells based on an NDI-selenophene copolymer (PNDIS-HD) acceptor and a thiazolothiazole copolymer (PSEHTT) donor exhibit a record 3.3% power conversion efficiency. The observed short circuit current density of 7.78 mA/cm 2 and external quantum efficiency of 47% are also the best such photovoltaic parameters seen in all-polymer solar cells so far. This efficiency is comparable to the performance of similarly evaluated [6,6]-Phenyl-C 61-butyric acid methyl ester (PC60BM)/PSEHTT devices. The lamellar crystalline morphology of PNDIS-HD, leading to balanced electron and hole transport in the polymer/polymer blend solar cells accounts for its good photovoltaic properties.
- Earmme, Taeshik,Hwang, Ye-Jin,Murari, Nishit M.,Subramaniyan, Selvam,Jenekhe, Samson A.
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supporting information
p. 14960 - 14963
(2013/11/06)
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- Solution-processable tetrazine and oligothiophene based linear A-D-A small molecules: Synthesis, hierarchical structure and photovoltaic properties
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A series of high coplanar alternative linear small molecules with acceptor-donor-acceptor (A-D-A) structure containing electron-accepting tetrazine (Tz) moiety and electron-donating oligothiophenes (OTs) moiety, alkylated thiophene attached to both sides of the Tz moiety were designed and synthesized. The influences of varied oligothiophene length on small molecules' optical and electrochemical properties, crystallization, self assembling morphology in blend film with (6,6)-phenyl-C61-butyric acid methyl ester (PC61BM), and photovoltaic properties for the application as donor materials in organic solar cells (OSCs) were studied. The optical and electrochemical properties of small molecules showed that the HOMO and LUMO energy levels were determined by the number of OTs moiety and electron-accepting ability of Tz in the alternative small molecules, respectively. Meanwhile, the varied OT moieties can significantly affect the hierarchical structures when mixed with PC61BM. The molecule with intermediate conjugate moity length showed the highest ordering in its crystalline state, as revealed by differential scanning calorimetry (DSC) and X-ray diffraction experiments, and best photovoltaic properties when blended together with PC61BM or (6,6)-phenyl-C71-butyric acid methyl ester (PC71BM) as active layer in photovoltaic devices. The results indicate that hierarchical structures controlled by adjusting the conjugate moity length of small molecules is an effective way to improve the performance of OSCs. The photovoltaic device based on TT(HTTzHT)2:PC71BM with 1% DIO additives showed the best performance, with a Jsc of 7.87 mA/cm2 and a PCE of 3.24%.
- Chen, Yujin,Li, Chao,Zhang, Pan,Li, Yaowen,Yang, Xiaoming,Chen, Liwei,Tu, Yingfeng
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p. 1424 - 1434
(2013/07/05)
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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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- Effect of oligothiophene π-bridge length on the photovoltaic properties of D-A copolymers based on carbazole and quinoxalinoporphyrin
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A series of low-bandgap donor-acceptor (D-A) copolymers, P(C-T-QP), P(C-BT-QP), P(C-TT-QP), and P(C-TT-QP-Zn), using 2,7-carbazole (C) as an electron-rich unit and quinoxalino[2,3-b]porphyrins (QP) or quinoxalino[2,3-b] porphyrinatozinc(QP-Zn) as an electron-deficient unit with different length of oligothiophene π-bridges, were designed and synthesized via a Pd-catalyzed Stille-coupling method. The π-bridge between the C donor unit and the QP acceptor unit is thiophene (T) in P(C-T-QP), bithiophene (BT) in P(C-BT-QP), and terthiophene (TT) in P(C-TT-QP) or P(C-TT-QP-Zn). These copolymers possess good solubility, high thermal stability, broad absorption, and low bandgap ranging from 1.66 to 1.73 eV. The influence of the π-bridge and the central Zn ion on the electronic and photovoltaic properties was investigated and discussed in detail. It was found that the π-bridge played an important role in tuning the effective conjugation length and therefore significantly affected the molecular architecture and optoelectronic properties of the copolymers. With the π-bridge varying from thiophene to bithiophene, then to terthiophene, the hole mobility of the copolymers increased gradually, and the absorption was broadened in turn. Zn ion in the porphyrin ring also had a significant influence on the physicochemical and photovoltaic properties. Bulk heterojunction solar cells with the polymers as donor and PC71BM as acceptor demonstrated PCEs of 0.97% for P(C-T-QP), 1.97% for P(C-BT-QP), 2.53% for P(C-TT-QP), and 1.45% for P(C-TT-QP-Zn). All of them are among the highest PCE values of PSCs based on porphyrin polymers. Among the four polymers, although the P(C-TT-QP-Zn) shows the highest hole mobility and the widest absorption, the corresponding PSC demonstrated the lowest PCE because the morphology of P(C-TT-QP-Zn)/PC 71BM blend film is not beneficial to the exciton dissociation and charge carriers transport. This study provides a new insight toward the design and future development of quinoxalinoporphyrin-based conjugated polymers.
- Shi, Shaowei,Jiang, Pei,Sun, Yeping,Wang, Xiaochen,Wang, Kai,Li, Xiaoyu,Wang, Haiqiao,Shen, Suling,Li, Yongfang,Chen, Song
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p. 7806 - 7814,9
(2020/09/15)
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- Chemoselective cross-coupling reactions with differentiation between two nucleophilic sites on a single aromatic substrate
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A new thiophene building block, containing both a stannyl group and a boronic ester, was prepared. From this starting material, a general, nucleophile-selective one-pot reaction was developed, exploiting the different reactivities of the Stille and Suzuki-Miyaura cross-coupling reactions. A series of aromatic electrophiles were used to demonstrate the high functional group tolerance.
- Linshoeft, Julian,Heinrich, Annika C. J.,Segler, Stephan A. W.,Gates, Paul J.,Staubitz, Anne
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supporting information
p. 5644 - 5647
(2013/01/15)
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- Synthesis and optical properties of 1,1-binaphthyl-thiophene alternating copolymers with main chain chirality
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A series of axially chiral 1,1-binaphthyl-thiophene copolymers were synthesized by Migita-Kosugi-Stille polycondensation and electrochemical polymerization. The polymers exhibit circular dichroism not only in the ultraviolet region but also in the visible region, both in solution and film states. Optical and electrochemical properties of the polymers are in good agreement with theoretical results obtained by density functional theory calculations. Although effective conjugation of the polymers was cleaved at the orthogonally oriented two naphthalene rings in the 1,1-binaphthyl unit, the electrochemically synthesized polymer film shows good electrochemical redox behavior with repeatable changes in optical absorption and circular dichroism. The changes in circular dichroism may reflect a change in the dihedral angle of the binaphthyl unit caused by reorientation of conjugated main chains between oxidized and neutral states. The Royal Society of Chemistry 2012.
- Kawabata, Kohsuke,Goto, Hiromasa
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p. 23514 - 23524
(2013/02/25)
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- HEPATITIS C VIRUS INHIBITORS
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The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS5A protein
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Page/Page column 274-275
(2011/07/30)
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- Synthesis of α-Thiophene Oligomers via Organotin Compounds
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A versatile synthetic route involving the use of organotin compounds hasbeen applied for the preparation of functionalized oligothiophenes. Thu s, substituted α-bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 2-trimethylstannylthiophene. The latter reagent couples with 2,5-dibromothiophenes to give the α-tertiophenes which are also accessible through the reaction of 5-trimethylstannyl-α-bithiophene with 2-bromothiophenes. 2,5-Bis(trimethylstannyl)thiophene and 5,5'-bis(trimethylstannyl)α-bithiophene react with 2-bromothiophenes to give α-tertiophenes and α-quarterthiophenes, respectively. α-Quarterthiophene is also produced via thereaction of 5-trimethylstannylthiophene with 5,5'-dibromo-α-bithi ophene. The coupling reaction of 5-trimethylstannyl-α-bithiophene with 2,5-dibromothiophene affords the α-quinquethiophene. The structures of the new compounds were confirmed by elemental analysis, Mass spectrometry, (1)H- and (13)C-NMR spectral data.
- Kamal, Marwan R.,Al-Taweel, Samir A.,El-Abadelah, Mustafa M.,Abu Ajaj, Khalid M.
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- SYNTHESIS AND REACTIVITY OF THE 2,5-BIS(TRIMETHYLSTANNYL) DERIVATIVES OF THIOPHENE AND FURAN
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The synthesis of the 2,5-bis(trimethylstannyl) derivatives of thiophene and furan is reported.Conditions for monotransmetalation and electrophilic destannylation are described.
- Seitz, David E.,Lee, Shi-Hung,Hanson, Robert N.,Bottaro, Jeffrey C.
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p. 121 - 128
(2007/10/02)
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