- Side-Chain-Induced Rigid Backbone Organization of Polymer Semiconductors through Semifluoroalkyl Side Chains
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While high-mobility p-type conjugated polymers have been widely reported, high-mobility n-type conjugated polymers are still rare. In the present work, we designed semifluorinated alkyl side chains and introduced them into naphthalene diimide-based polymers (PNDIF-T2 and PNDIF-TVT). We found that the strong self-organization of these side chains induced a high degree of order in the attached polymer backbones by forming a superstructure composed of "backbone crystals" and "side-chain crystals". This phenomenon was shown to greatly enhance the ordering along the backbone direction, and the resulting polymers thus exhibited unipolar n-channel transport in field-effect transistors with remarkably high electron mobility values of up to 6.50 cm2 V-1 s-1 and with a high on-off current ratio of 105.
- Kang, Boseok,Kim, Ran,Lee, Seon Baek,Kwon, Soon-Ki,Kim, Yun-Hi,Cho, Kilwon
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- New dithienophosphole-based donor-acceptor alternating copolymers: Synthesis and structure property relationships in OFET
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Two donor-acceptor conjugated copolymers comprised of a novel dithienophosphole (DTP) as the acceptor unit and bithiophene (BT) or decylthiophenebenzodithiophene (DTBDT) as the donor unit were synthesized and characterized to elucidate the relationship between donor-acceptor (D-A) architecture and organic field-effect transistors (OFETs) performance. These characteristics of D-A copolymers were affected by the structural suitability of donor and acceptor units. Poly(DTP-BT) had an ordered structure that facilitated charge carrier transfer. The crystallinity of poly(DTP-BT) increased as annealing temperature (Tann) increased. In contrast, poly(DTP-DTBDT) was amorphous regardless of Tann due to the long alkyl chains of the DTBDT units. OFET devices made with poly(DTP-BT) and annealed at 200°C exhibit a highly crystalline morphology and a relatively high field-effect mobility (4.9 × 10-3 cm2/(V·s)).
- Sung, Min Jae,Kim, Yebyeol,Lee, Sang Bong,Lee, Gi Back,An, Tae Kyu,Cha, Hyojung,Kim, Se Hyun,Park, Chan Eon,Kim, Yun-Hi
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- Direct arylation polymerization toward a narrow bandgap donor–acceptor conjugated polymer of alternating 5,6-difluoro-2,1,3-benzothiadiazole and alkyl-quarternarythiophene: From synthesis, optoelectronic properties to devices
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ABSTRACT: Direct arylation polymerization (DAP) enabled facile synthesis of a narrow bandgap donor–acceptor conjugated polymer (PDFBT-Th4) composed of alternating 5,6-difluoro-2,1,3-benzothiadiazole and alkyl-quaternarythiophene. The optimized reaction condition of DAP catalyzed with Pd(OAc)2/(o-MeOPh)3P/PivOH/K2CO3 in o-xylene led to the target polymer with a number-average molecular weight (Mn) of 14.6 kDa without noticeable homocoupling or β-branching defects. UV-vis absorption spectra of PDFBT-Th4 indicate strong interchain aggregation in films. While the C-H selectivity and the alternating polymer structure of PDFBT-Th4 synthesized via DAP are comparable to those of the same type polymers synthesized via Stille coupling, the batch of PDFBT-Th4 synthesized via optimal DAP, despite its lower Mn, showed higher hole mobility in field effect transistors and larger power conversion efficiency in organic solar cell devices. These results further demonstrate the promising potential of DAP for efficient synthesis of high-performance D-A conjugated polymers for broad optoelectronic applications.
- Efrem, Amsalu,Wang, Kai,Jia, Tao,Wang, Mingfeng
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- Synthesis and properties of 2- or 2,5-substituted thiophene and 2- or 2,5'-substituted dithiophene derivatives of platinum
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The reaction of (COD = cycloocta-1,5-diene) with 2,5-bis(trimethylstannyl)thiophene or with 2,5'-bis(trimethylstannyl)-5-(2'-thienyl)thiophene gives diplatinum complexes bridged with 2,5-thienylene or 2,5'-di(5,2'-thienylene), Cl(COD)Pt(μ-2,
- Kotani, S.,Shiina, K.,Sonogashira, K.
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- Ortho-bridged perylene diimide dimer and preparation method thereof as well as application thereof in organic photovoltaic devices
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The invention provides an ortho-bridged perylene diimide dimer (formula I), a preparation method and an application thereof in the organic photovoltaic field. The invention further relates to an organic solar cell of the compound and a preparation method of the organic solar cell. Compared with a PDI monomer molecule, a formed twisted dimer structure is capable of effectively weakening excessive aggregation among PDI molecules, so that the phase size is reduced. Meanwhile, by virtue of ortho-bridging, the deformation of a PDI inner core caused by waist bridging can be avoided, so that certain planarity and relatively strong pi-pi accumulation can be maintained, and relatively high electronic mobility can be obtained. The PDI dimer is taken as a receptor material and is combined with an electron donor polymer so as to prepare the organic solar cell, so that very high photoelectric conversion efficiency is realized.
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Paragraph 0063-0065
(2020/07/23)
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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; 0197; 0200-0202
(2018/05/03)
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- A molecular structure and crystallization correlation study of pyromellitic diimide-based conjugated copolymers
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Three pyromellitic diimide(PMDI)-based polymers—poly(pyromellitic diimide-co-bithiophene) [poly(PMDI-BTh)], poly(pyromellitic diimide-co-tetrathiophene) [poly(PMDI-TTh)], and poly(pyromellitic diimide-co-benzodithio- phene) [poly(PMDI-BDTTh)]—are synthesized to study the influence of different thiophene-containing electron-donating groups on the crystallizability of PMDI-based conjugated polymers. Computer simulation using Density Functional Theory (DFT) [Gaussian B3LYP/6–31 + G(d,p)] indicates that poly(PMDI-BDTTh) has a more planar molecular structure than the other two copolymers. Powder XRD diffraction experiment of the poly(PMDI-BDTTh) shows a diffraction peak at about 2θ = 6.0°, but no diffraction peak occurs for poly(PMDI-BTh) and poly(PMDI-TTh). Although PMDI is a planar structure that is favorable for the molecular aggregation, a comonomer with planar structure seems to be very crucial in order to synthesize a crystallizable push–pull-type PMDI-based conjugated copolymer.
- Tsai, Ming-Chia,Liu, Ja-Wei,Huang, Ping-Tsung
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p. 828 - 834
(2018/03/21)
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- A two-dimensional molecule with a large conjugation degree: Synthesis, two-photon absorption and charge transport ability
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A new molecule, 5,5′-bis(4,6-bis((E)-4-(octyloxy)styryl)pyrimidin-2-yl)-2,2′-bithiophene (OSPB), was designed and synthesized. It contains two D-π-A-π-D (donor-π-acceptor-π-donor) segments with an alkoxy group D and a pyrimidine moiety A, and these two segments are connected through a bithiophene moiety to shape a two-dimensional (2D) multibranched conjugated system. The molecule showed high thermal stability. It demonstrated good solubility in THF with an emission maximum at 470 nm, and excimer emission appeared in poor solvents such as aqueous media showing an obvious red-shift. A two-photon excited fluorescence (TPEF) test revealed that the maximal two-photon absorption (2PA) cross-section of the molecule was 1352 GM, which is comparable with the reported bipyrimidine-based multibranched compounds with a stronger donor. Theoretical calculation suggested that the molecule showed good coplanarity made up by two conjugated segments with a small dihedral angle. The charge transport ability of OSPB was preliminarily studied using an organic thin-film transistor (OTFT) device via a low-cost solution processing technique, and the results demonstrated that it was a p-type semiconductor.
- Chen, Dugang,Zhong, Cheng,Zhao, Yan,Nan, Lingyan,Liu, Yunqi,Qin, Jingui
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supporting information
p. 5199 - 5206
(2017/07/10)
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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 0053
(2017/08/30)
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- Low threshold amplified spontaneous emission and ambipolar charge transport in non-volatile liquid fluorene derivatives
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Highly fluorescent non-volatile fluidic fluorene derivatives functionalized with siloxane chains were synthesized and used in monolithic solvent-free liquid organic semiconductor distributed feedback lasers. The photoluminescence quantum yield values, the
- Ribierre, Jean-Charles,Zhao, Li,Inoue, Munetomo,Schwartz, Pierre-Olivier,Kim, Ju-Hyung,Yoshida, Kou,Sandanayaka, Atula S. D.,Nakanotani, Hajime,Mager, Loic,Méry, Stéphane,Adachi, Chihaya
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supporting information
p. 3103 - 3106
(2016/02/23)
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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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- Geometrically controlled organic small molecule acceptors for efficient fullerene-free organic photovoltaic devices
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Organic small molecule (SM) acceptors containing a perylene diimide (PDI) moiety, F2B-T2PDI and T2PDI are synthesized, and the effects of their molecular geometry on the performance of fullerene-free organic photovoltaic (OPV) devices are investigated. Th
- Hadmojo, Wisnu Tantyo,Nam, So Youn,Shin, Tae Joo,Yoon, Sung Cheol,Jang, Sung-Yeon,Jung, In Hwan
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p. 12308 - 12318
(2016/08/13)
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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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- 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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- 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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- 2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione-based donor-acceptor alternating copolymer bearing 5,5′-Di(thiophen-2-yl)-2, 2′-biselenophene exhibiting 1.5 cm2·V -1·s-1 hole mobility in thin-film transistors
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A novel diketopyrrolopyrrole-based π-conjugated copolymer P(DPP-alt-DTBSe), 5, and a known copolymer P(DPP-alt-QT), 4, have been synthesized in 80-90% yield using the Stille coupling reaction. The molecular weights of 4 and 5 are 58 781 and 19 271 g/mol, respectively, with polydispersity values of 3.25-3.35. A relatively small band gap of 1.32-1.39 eV and excellent solubility in organic solvents were achieved in the two polymers. Thin-film transistors made of 5 exhibit outstanding performance (e.g., μ > 1.0-1.5 cm2·V-1·s-1, I on/Ioff > 105-106) with a conventional n-octyltrichlorosilane-SiO2 gate dielectric.
- Ha, Jae Seung,Kim, Kyung Hwan,Choi, Dong Hoon
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p. 10364 - 10367
(2011/09/13)
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- DIOXYPYRROLO-HETEROAROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICES USING THE SAME
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The present invention relates to dioxypyrrolo-heterocyclic compounds and an organic electronic device using the same. The compound of the present invention satisfies the requirements for use in an organic electronic device such as an organic light emitting device, an organic thin film transistor, and an organic solar cell, for example, suitable energy levels, and the electrochemical and thermal stability, by introducing various substituents to the core structure, and also have amorphous or crystalline property depending on the Mnd of the substituents, to satisfy the characteristics individually required for each of the devices. Further, an organic semi-conductor of p-type or n-type can be fabricated by introducing various substituents to the core structure having a property of n-type, thereby providing stability for the device.
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- Method useful for amplifying, detecting and depleting pathologic forms of the cellular prion protein
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The present invention relates to a method for selectively amplifying the oligomerization of at least one PrPSc isoform of the PrPC cellular prion protein, characterized in that it comprises bringing said PrPSc isoform, under conditions suitable for amplification, together with an effective amount of at least one compound of general formula I as follow: The instant invention is also directed to new compounds of formula I and pharmaceutical compositions including them.
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Page/Page column 8-9
(2009/07/17)
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- DIOXYPYRROLO-HETEROAROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICES USING THE SAME
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The present invention relates to dioxypyrrolo-heterocyclic compounds and an organic electronic device using the same. The compound of the present invention satisfies the requirements for use in an organic electronic device such as an organic light emitting device, an organic thin film transistor, and an organic solar cell, for example, suitable energy levels, and the electrochemical and thermal stability, by introducing various substituents to the core structure, and also have amorphous or crystalline property depending on the Mnd of the substituents, to satisfy the characteristics individually required for each of the devices. Further, an organic semi-conductor of p-type or n-type can be fabricated by introducing various substituents to the core structure having a property of n-type, thereby providing stability for the device.
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Page/Page column 19-20
(2008/12/08)
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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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