- Tuning photoluminescent wavelength of water-soluble oligothiophene/polymer complex film by proton bonding
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We synthesized a new oligothiophene derivative with pyridine end groups and investigated their optical properties. Upon adding an aqueous polystyrene sulfonic acid solution, it forms homogeneous polymer complex films with protonated structure. Furthermore
- Kondo, Mizuho,Miyake, Jun-Ichi,Tada, Kazuya,Kawatsuki, Nobuhiro
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- Relationship between the energy levels and the photovoltaic properties of oligothiophenes
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A series of linear π-conjugated oligothiophenes, α,α'- dihexylquinquethiophene (DH5T), 2,5-bis(5'-hexyl-2,2'-bithiophene-5-yl)thieno[3, 2-b]thiophene (DH5TT), and α, α'-dihexylheptathiophene (DH7T), has been synthesized using the Suzuki coupling reaction. The optical and electrochemical properties of oligothiophenes were easily tuned by controlling the thiophene number. The UV-vis absorption and photoluminescence (PL) spectra are gradually red-shifted on going from DH5T and DH5TT to DH7T due to the increase in α-conjugation length. The energy band gap decreased as the oligothiophene length increased. The optical band gaps of DH5T, DH5TT, and DH7T occur at 2. 39, 2.25, and 2.01 eV, respectively. Bulk heterojunction organic photovoltaic cells (OPVs) fabricated from oligomers showed the power conversion efficiency of 0.45-0.8% under AM 1.5 (100 mW/cm2). Among them, DH5T showed the best OPV performance of an open circuit voltage (VOC) of 0.51 V, short-circuit current (JSC) of 4.25 mA/cm2, and fill factor (FF) of 0.37, resulting in the power conversion efficiency of 0.80%. Moreover, the relationship between conjugation length and photovoltaic properties was systematically investigated in terms of the energy band gap and open circuit voltage (VOC). Copyright
- Lim, Eunhee
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- PROCESS FOR PRODUCTION OF OXIDATION REACTION PRODUCT OF AROMATIC COMPOUND
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The present invention provides a process for producing an oxidation reaction product of an aromatic compound, having excellent environmental load reduction performance, cost reduction performance, etc. Provided is a process for producing an oxidation reaction product of a raw material aromatic compound by reacting the raw material aromatic compound with an oxidizing agent. The process further uses an electron donor-acceptor linked molecule. The process includes the step of: reacting the electron donor-acceptor linked molecule in an electron-transfer state, the oxidizing agent, and the raw material aromatic compound, thereby generating an oxidation reaction product resulting from oxidation of the raw material aromatic compound.
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Page/Page column 19
(2012/07/14)
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- A novel method for the bromination of thiophenes
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A novel, fast and convenient method for the bromination of thiophenes and oligothiophenes with N-bromosuccinimide (NBS) using ultrasonic irradiation is elaborated. The yield of bromothiophenes strongly depends on the initial thiophene structure and nature of the solvent.
- Arsenyan, Pavel,Paegle, Edgars,Belyakov, Sergey
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scheme or table
p. 205 - 208
(2010/03/24)
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- Synthesis and photovoltaic properties of formyl end-capped oligothiophenes
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For the purpose of developing novel photovoltaic materials, 5,5″-biformyl-2,2′:5′,2″-terthiophene (OHC-3T-CHO) and 5,5″-biformyl-2,2′:5′,2″:5″,2?:5?, 2″″-q-uinquethiophene (OHC-5T-CHO) were synthesized. The photovoltaic properties of OHC-3T-CHO and OHC-5T-CHO were studied. We have fabricated two flexible organic photovoltaic devices using OHC-3T-CHO, OHC-5T-CHO, and 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA). The PET-ITO (indium tin oxides coated with polyethylene terephthalate)/OHC-3T-CHO/ PTCDA/Al device has an open circuit voltage (Voc) of 1.12V, and photoelectric conversion efficiency (PCE) of 1.00%, whereas the PET-ITO/OHC-5T-CHO/PTCDA/Al device has a Voc of 1.78V and PCE of 1.08%. Both devices have high Voc (1.12V and 1.78V). It is possible that intermolecular hydrogen bonding between the -CHO group of OHC-nT-CHO and the carboxylic dianhydride of PTCDA enhanced the efficiency by promoting forward interfacial electron transfer.
- Jiang, Chuanyu,Liu, Ping,Deng, Wenji
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experimental part
p. 2360 - 2369
(2009/11/30)
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- Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives
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In order to develop novel oligothiophene-based liquid crystals capable of hydrogen bonding, new terthiophene derivatives containing an alkylamide group, N,N′-dialkyl-5,5″-dichloro-2,2′:5′,2″- terthiophene-4,4″-dicarboxamide (DNCnDCl3T, n=8, 18)
- Liu, Ping,Zhang, Yamin,Feng, Guiju,Hu, Jianhua,Zhou, Xiaoping,Zhao, Qizhong,Xu, Yunhua,Tong, Zhen,Deng, Wenji
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p. 5259 - 5264
(2007/10/03)
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- Synthesis of extended α,α'-oligo(silylthiophenes) by cerium(IV) oxidative coupling reactions
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Cerium(IV) oxidative dimerisations of 4,4'-bis(trimethylsilyl)-2,2':5',2''-terthiophene and the quaterthienyl analogue 1c gave the corresponding sexi- and octi-thiophenes; the latter have been used to prepare α-linked hexadecithiophene and tetracosithiophene derivatives.
- Mustafa, Ali H.,Shepherd, Michael K.
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p. 2743 - 2744
(2007/10/03)
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- Synthesis and Characterization of α,α'-Bis(aminomethyl)oligothiophenes and Their Related Compounds
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We have synthesized and characterized a series of novel compounds of α,α'-bis(aminomethyl)oligothiophenes and their related compounds whose degree of polymerization spans two (dimer) to five (pentamer). The compounds presented in our studies are α,α'-bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopenthyl)methyl] oligothiophene, α,α'-bis(aminomethyl)oligothiophene dihydrochloride and α,α'- bis(aminomethyl)oligothiophene. These compounds exhibit desired chemical activity while maintaining controllable electronic properties. The synthetic processes of the oligothiophenes are as follows: 2-aminomethylthiophene is first 'protected' and the thiophene rings are coupled using standard Grignard methods. The protected groups are removed at the final stage of the reaction. The compounds show unique properties; for example α,α'-bis(aminomethyl)oligothiophene dihydrochloride is soluble in water. The results of electronic spectra and duration are also presented.
- Muguruma, Hitoshi,Saito, Takashi,Sasaki, Satoshi,Hotta, Shu,Karube, Isao
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p. 173 - 178
(2007/10/03)
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- Preparation of extended di(4-pyridyl)thiophene oligomers
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Different methods for the coupling of 2-(4-pyridyl)thiophene to α-dibrominated thiophene oligomers and their efficiency to produce a homologous series of extended di(4-pyridyl)thiophene oligomers have been studied. The coupling was found to be most efficient with the organozinc derivative of 2-(4-pyridyl)thiophene, using a Pd(dppf) complex as the catalyst in the coupling reaction. The resulting compounds are promising new models for trans-membrane molecular conductors.
- Alberst, Willem M.,Canters, Gerard W.,Reedijk, Jan
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p. 3895 - 3904
(2007/10/02)
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- Selective synthesis of α-substituted oligothiophenes
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An improved synthesis of selectively mono- and dibrominated oligothiophenes using the system N-bromosuccinimide/dimethylformamide is reported together with the preparation of the corresponding α-alkyl and α,α-dialkyl derivatives which represent potent biologically active agents.
- Bauerle,Wurthner,Gotz,Effenberger
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p. 1099 - 1103
(2007/10/02)
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- Novel Electron Acceptors Bearing a Heteroquinonoid System. I. Synthesis and Conductive Complexes of 5,5'-Bis(dicyanomethylene)-5,5'-dihydro-Δ2,2'-bithiophene and Related Compounds
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Novel electron acceptors bearing a heteroquinonoid system, 5,5'-bis(dicyanomethylene)5,5'-dihydro-Δ2,2'-bithiophene, its 3,3'-dichloro, 3,3'-dibromo, and 3,3',4,4'-tetrabromo derivatives, and 5,5''-bis(dicyanomethylene)-5,5''-dihydro-Δ2,2':5',2''-tertiophene were synthesized by the action of tetracyanoethylene oxide or by Pd(0)-catalyzed substitution reactions with sodium dicyanomethanide on the corresponding α,α'-dihalogeno-heteroaromatics.They showed very small on-site Coulomb repulsion as expected, and afforded several highly conductive molecular complexes with electron donors such as hexamethylenetetratellurafulvalene.
- Yui, Koji,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
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p. 1539 - 1546
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF 2,5-THIENYLENE OLIGOMERS; SOME OF THEIR SPECTROSCOPIC AND ELECTROCHEMICAL PROPERTIES
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Key words: 2,5-Thienylene oligomers, UV spectra, oxidation potentials, cyclic voltammetry.A convenient synthesis of a number of oligomeric thiophenes and oligomeric methyl-, and ethyl-substituted thiophenes as bulding blocks for novel conducting polymers is reported.The synthesis is based on a NiCl2(dppp) (dppp=Ph2PCH2CH2CH2PPh2) catalyzed coupling reaction between appropriately substituted bromothiophenes and Grignard compounds derived of them.The λmax of the UV spectra of the unsubstituted oligomeric thiophenes increases, as expected, with the number of thiophene units in the oligomers.Also, as expected, the oxidation potential Eox of these compounds decreases with increasing the number of thiophene units.In the series of the methyl- or ethyl-substituted oligomeric thiophenes such a clear cut relationship is not observed.This behavior is discussed on the basis of diminishing coplanarity due to steric hindrances by the alkyl groups in the 3,3'-positions, which results in a blue shift of the λmax of the UV spectra and decreased stability of the radical cation formed upon electrooxidation, manifesting itself by a higher oxidation potential.
- Pham, Chiem Van,Burkhardt, A.,Shabana, R.,Cunningham, David D.,Mark, Harry B.,Zimmer, Hans
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p. 153 - 168
(2007/10/02)
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- SYNTHESIS AND CHARACTERIZATION OF ALKYL-, HALO- AND HETEROSUBSTITUTED DERIVATIVES OF THE POTENT PHOTOTOXIN &α-TERTHIENYL
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A number of derivatives of α-terthienyl were prepared including a series of naturally occurring compounds.A description of the syntheses of some new compounds, including 5-iodo, 5,5''-diiodo, 5,5''-diformyl, 5,5''-di-tert butyl, 5-tert-butyl, 5-tert-butoxy, 5-trimethylsilyl, 5-thiomethyl, 5,5''-dithiomethyl and 5-carboxyl-5''-(trimethylsilyl)-2,2':5',2''-terthienyl is also given.An analysis of the 1H NMR data of the derivatives is presented.
- Eachern, Anita Mac,Soucy, Chantal,Leitch, Leonard C.,Arnason, John T.,Morand, Peter
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p. 2403 - 2412
(2007/10/02)
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- PREPARATION OF α-QUATER-, α-SEXI, AND α-OCTITHIOPHENES
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α-Quaterthiophene (1), α-sexithiophene (2), and α-octithiophene (3) (the highest member of α-oligothiophenes ever synthesized) were prepared from α-bithiophene, α-terthiophene, and α-quaterthiophene, respectively, via monobromination with N-bromosuccinimide followed by reductive coupling reaction with an activated nickel(0) reagent.
- Nakayama, Juzo,Konishi, Toru,Murabayashi, Shigeru,Hoshino, Masamatsu
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p. 1793 - 1796
(2007/10/02)
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