1081-34-1Relevant articles and documents
Synthesis and Cyclization-Induced Charge Transfer of Rectangular Bisterthiophenesiloxanes
Li, Chensen,Hu, Jian,Tashiro, Kohji,Ren, Zhongjie,Yan, Shouke
, p. 13701 - 13704 (2019)
Cyclization-modified terthiophene displays the change of emission behavior from locally excited (LE) to the intramolecular charge transfer (ICT) state. The rectangular bisterthiophenesiloxanes (DSiTh) was successfully prepared by π–π-stacking-aided hydrogen-bonding interactions. Cyclization-induced ICT in DSiTh could be observed, which was confirmed by absorption spectra, fluorescence spectra, and quantum chemistry analysis. The cyclization produces a strong intramolecular electron redistribution of a highly packed π-conjugated terthiophene. Thus, a distinctive variation of the dipole moment and a through-space ICT happen.
Solution-phase microwave-assisted synthesis of unsubstituted and modified α-quinque- and sexithiophenes
Melucci,Barbarella,Zambianchi,Di Pietro,Bongini
, p. 4821 - 4828 (2004)
The facile synthesis of poorly soluble unsubstituted and modified α-quinque- and sexithiophenes under microwave irradiation in the liquid phase is described. The use of microwave irradiation allowed these compounds to be prepared in a few minutes and at high yields by means of the Suzuki cross-coupling reaction. Unsubstituted sexithiophene was obtained in 10 min via the one-pot borylation/Suzuki reaction, purified according to a very simple procedure, and isolated in 84% yield. The efficient synthesis of two new methylated quinque- and sexithiophenes displaying liquid crystalline properties is reported. A new microwave-assisted methodology for the conversion of aldehyde-terminated quinque- and sexithiophenes into the corresponding cyano derivatives is also described. The use of microwaves was extended to the Sonogashira coupling reaction and found to be very effective in the preparation of a quinquethiophene containing acetylenic spacers. The electronic and optical characterization of this compound is reported and discussed in relation to that of unsubstituted quinquethiophene.
Trisulfur radical anion as the key intermediate for the synthesis of thiophene via the interaction between elemental sulfur and NaO t Bu
Zhang, Guoting,Yi, Hong,Chen, Hong,Bian, Changliang,Liu, Chao,Lei, Aiwen
, p. 6156 - 6159 (2014)
A facile base-promoted sulfur-centered radical generation mode and a single-step protocol for the synthesis of thiophene derivatives using 1,3-diynes via the interaction between elemental sulfur and NaOtBu has been reported. EPR experiments revealed that the trisulfur radical anion acts as a key intermediate of this process. A plausible mechanism has been proposed.
Influence of the molecular orientation of oligothiophene derivatives in vacuum-evaporated thin films on photovoltaic properties
Hu, Jianhua,Liang, Lusheng,Chen, Tuhua,Liu, Ping,Deng, Wenji
, p. 158 - 161 (2014)
To understand the relationship between molecular orientation in organic thin films and organic photovoltaic properties the donor-acceptor type oligothiophene derivatives 5,5″-dicyano-2,2′:5′,2″- terthiophene and 5,5?-dicyano-2,2′:5′,2″:5″, 2?-quaterthiophene were synthesized. Polarizing optical microscopy showed that the oligothiophene derivatives had liquid crystalline properties. The crystalline phases of the oligothiophene derivatives showed molecular orientation. Atomic force microscopy also showed that the vacuum-evaporated oligothiophene derivative thin films had molecular orientation. Using the oligothiophene derivative thin films as donor materials and a 3,4,9,10-perylenetetracarboxylic dianhydride thin film as the acceptor material organic photovoltaic devices were fabricated. The structure of these devices is glass-indium tin oxide/donor materials/acceptor material/aluminum. The molecular orientation of the vacuum-evaporated oligothiophene derivative thin films was found to improve the organic photovoltaic performance of these devices.
Supramolecular formation of fibrous nanostructure in donor-acceptor dyad film
Nishizawa, Takeshi,Tajima, Keisuke,Hashimoto, Kazuhito
, p. 2440 - 2445 (2007)
A novel oligothiophene and its fullerene derivative were synthesized and their film morphologies were investigated. AFM images revealed that the oligothiophene formed well-aligned fiber-like nanostructures in the film after being thermally annealed at its liquid-crystalline temperature. In the oligothiophene-fullerene dyad film, fibers were already formed in the as-cast film. Thermal annealing further enhanced the structural order and a long, partially aligned fibrous nanostructure with a width of around 10 nm and a length of as long as 200 nm was observed. Combined with the results of X-ray analysis, these features were ascribed to supramolecular self-assembly via π-π interaction of the oligothiophene groups. Photovoltaic properties of the molecules were also investigated. The Royal Society of Chemistry.
Synthesis and antiproliferative activity of RITA and its analogs
Jiang, Jianhua,Ding, Chao,Li, Lulu,Gao, Chunmei,Jiang, Yuyang,Tan, Chunyan,Hua, Ruimao
, p. 6635 - 6638 (2014)
The synthesis of RITA and a variety of five-membered heterocyclic triads by the cyclocondensation of 1,4-bis(5-substituted-2-thienyl or 2-furyl)-1,3-butadiynes with water or Na2S·9H2O in the presence of KOH in DMSO is described. The study on the antiproliferative activities against K562, MCF-7, A549, and HCT116 tumor cells has revealed that some of the heterocyclic triads show higher antiproliferative activities than RITA, depending on the structures of substituents, the property of heteroatoms as well as their numbers.
THE SYNTHESIS OF ALPHA-THIOPHENE OLIGOMERS VIA ORGANOBORANES
Kagan, Jacques,Arora, Sudershan K.
, p. 4043 - 4046 (1983)
Oligomers containing from 2 to 6 thiophene units attached by their 2 and 5 positions were synthesized unambiguously by iodine oxidation of a suitable ate complex obtained by stepwise reactions of 9-BBN with methanol, a 2-lithiothiophene, boron trifluoride etherate, and a second 2-lithiothiophene.This is a one-pot procedure, carried out under nitrogen between -80 deg C and 0 deg C.
Novel protein kinase C inhibitors: α-terthiophene derivatives
Kim, Darrick S. H. L.,Ashendel, Curtis L.,Zhou, Qin,Chang, Ching-Te,Lee, Eung-Seok,Chang, Ching-Jer
, p. 2695 - 2698 (1998)
A series of α-terthiophene derivatives were prepared and their protein kinase C inhibitory activity were evaluated. The aldehyde derivatives were most potent inhibitors (IC50 1 μM). 2a-Terthiophene monoaldehyde was inactive in the inhibitions of protein kinase A, mitogen activated protein kinase and protein tyrosine kinase.
Wavelength-Dependent Singlet Oxygen Generation in Luminescent Lanthanide Complexes with a Pyridine-Bis(Carboxamide)-Terthiophene Sensitizer
Gracia-Nava, Manuel A.,Johnson, Katherine R.,Rack, Jeffrey J.,Vittardi, Sebastian B.,de Bettencourt-Dias, Ana
, (2020)
Lanthanide ion (LnIII) complexes, [Ln(3Tcbx)2]3+ (LnIII=YbIII, NdIII, ErIII) are isolated with a new pyridine-bis(carboxamide)-based ligand with a 2,2′:5′,2′′-terthiophene pendant (3TCbx), and their resulting photophysical properties are explored. Upon excitation of the complexes at 490 nm, only LnIII emission is observed with efficiencies of 0.29 % at 976 nm for LnIII=YbIII and 0.16 % at 1053 nm for LnIII=NdIII. ErIII emission is observed but weak. Upon excitation at 400 nm, concurrent 1O2 formation is seen, with efficiencies of 11 % for the YbIII and NdIII complexes and 13 % for the ErIII complex. Owing to the concurrent generation of 1O2, as expected, the efficiency of metal-centered emission decreases to 0.02 % for YbIII and 0.05 % for NdIII. The ability to control 1O2 generation through the excitation wavelength indicates that the incorporation of 2,2′:5′,2′′-terthiophene results in access to multiple sensitization pathways. These energy pathways are unraveled through transient absorption spectroscopy.
Synthesis and liquid crystal properties of a novel family of oligothiophene derivatives
Liu, Ping,Zhang, Yamin,Feng, Guiju,Hu, Jianhua,Zhou, Xiaoping,Zhao, Qizhong,Xu, Yunhua,Tong, Zhen,Deng, Wenji
, p. 5259 - 5264 (2004)
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)
A colorimetric and fluorometric oligothiophene-indenedione-based sensor for rapid and highly sensitive detection of cyanide in real samples and bioimaging in living cells
Guo, Zongrang,Hu, Tingting,Sun, Tao,Li, Tianduo,Chi, Hong,Niu, Qingfen
, p. 667 - 674 (2019)
A new simple oligothiophene-indenedione-based sensor 3TI has been synthesized for the highly reactive and selective detection of cyanide anion (CN?) in 70% aqueous media. The sensor 3TI displays distinct colorimetric and fluorometric detection of CN? due to the addition of CN? to the electron-deficient indenedione-vinyl group of 3TI, which hampers intramolecular charge transfer (ICT) efficiencies. The recognition mechanism of 3TI for CN? was confirmed by the optical measurements, 1H NMR titration, FTIR spectra, HRMS analysis, and TD-DFT calculations. The sensor 3TI for CN? shows the outstanding advantages of high fluorescence brightness, fast response time (30 s), low detection limit (31.3 nM), minimal pH dependence in the physiologically relevant range, and excellent selectivity in presence of other competitive anions. Encouraged by these desirable sensing properties, the 3TI has been successfully used for determination of CN? in real water and food samples, silica-based sensing kits and fluorescence imaging in living cells with satisfactory results.
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
Yui, Koji,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
, p. 1539 - 1546 (1989)
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.
BIOSYNTHESIS OF 2,2';5' ,2"-TERTHIENYL IN THE COMMON MARIGOLD.
SCHUETZ,WAGGONER,BYERRUM
, p. 436 - 440 (1965)
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Sease,Zechmeister
, p. 270,271 (1947)
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Oligothiophene compounds inhibit the membrane fusion between H5N1 avian influenza virus and the endosome of host cell
Zhu, Zhibo,Liu, Shuwen,Yao, Zhili,Shen, Xiantian,Chen, Zhipeng,Liu, Xiangtao,Parquette, Jon R.,Liu, Shuwen
, p. 185 - 194 (2017)
Hemagglutinin (HA) which is essential for influenza viral infection and replication has become a target for the design of anti-influenza drugs. A novel series of oligothiophene compounds focused on the target were synthesized as specific inhibitors agains
The synthesis and photoactivated cytotoxicity of novel 5-phenyl-3-(2, 2′:5′,2″-terthien-5-yl)-4,5-dihydro-1H-pyrazolines
Luo, Zhi-Gang,Liu, Zheng-Yong,Yang, Zhuo-Hong
, p. 333 - 336 (2014)
A series of novel 5-phenyl-3-(2,2′:5′,2′′-terthien- 5-yl)-4,5-dihydro-1H-pyrazolines were synthesized in this report. Their photoactivated cytotoxicities on the Spodoptera litura (SL) cell line were evaluated using the MTT method. It was noticed that the inhibitory activities of all the conjugates was enhanced when irradiated with UV-A light. Compounds 4, 6 and 8 were found to be most effective with inhibition rates of 88.1%, 88.0%, and 90.5%, respectively. For compound 5, the inhibition rate value was only slightly enhanced under the irradiation treatment (78.3%) compared to the dark treatment (74.8%). The relationship analysis between structure and activity showed that the middle thiophene ring played an important role on the inhibitory activities. It was shown that these compounds could be the potential candidates for new photoactivated pesticides.
Novel low-bandgap oligothiophene-based donor-acceptor alternating conjugated copolymers: Synthesis, properties, and photovoltaic applications
Li, Yaowen,Li, Zaifang,Wang, Chunyu,Li, Hui,Lu, Hongguang,Xu, Bin,Tian, Wenjing
, p. 2765 - 2776 (2010)
A series of novel soluble donor-acceptor lowbandgap-conjugated polymers consisting of different oligothiophene (OTh) coupled to electron-accepting moiety 2-pyran-4ylidenemalononitrile (PM)-based unit were synthesized by Stille or Suzuki coupling polymerization. The combination of electron-accepting PM building block with varied OThn (the number of thiophene unit increases from 3 to 5) results in enhanced π-π stacking in solid state and intramolecular charge transfer (ICT) transition, which lead to an extension of the absorption spectra of the copolymers. Cyclic voltammetry measurements and molecular orbital distribution calculations indicate that the highest occupied molecular orbitals (HOMO) energy levels could be fine-tuned by changing the number of thiophene units of the copolymers, and the resulting copolymers possessed relatively low HOMO energy levels promising good air stability and high-open circuit voltage (Voc) for photovoltaic application. Bulk heterojunction photovoltaic devices were fabricated by using the copolymers as donors and (6,6)phenyl C61-butyric acid methyl ester as acceptor. It was found that the highest Voc reached 0.94 V, and the short circuit currents (Jsc) were improved from 1.78 to 2.54 mA/cm2, though the power conversion efficiencies of the devices were measured between 0.61 and 0.99% under simulated AM 1.5 solar irradiation of 100 mW/cm 2, which indicated that this series copolymers can be promising candidates for the photovoltaic applications.
Electrochromic properties of pyrene conductive polymers modified by chemical polymerization
Chang, Lijing,Hou, Yanjun,Li, Rui,Ma, Yang,Miao, Shoulei,Wang, Cheng,Xu, Haoran,Zhang, Yuhang
, p. 39291 - 39305 (2021/12/27)
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.
Trithiocarbonate Anion as a Sulfur Source for the Synthesis of 2,5-Disubstituted Thiophenes and 2-Substituted Benzo[ b]thiophenes
Paix?o, Douglas B.,Rampon, Daniel S.,Salles, Helena D.,Soares, Eduardo G. O.,Bilheri, Filipe N.,Schneider, Paulo H.
supporting information, p. 12922 - 12934 (2020/11/26)
The trithiocarbonate anion (CS32-) was generated in situ from CS2 and KOH in dimethyl sulfoxide by a simple method and used as a novel synthetic equivalent of the S2- synthon for the synthesis of 2,5-disubstituted thiophenes from 1,3-butadiynes. Additionally, this system was employed for the metal-free synthesis of 2-substituted benzo[b]thiophenes from 2-haloalkynyl (hetero)arenes. These compounds were obtained from a cheap and readily available sulfur source in moderate to good yields, with good functional group tolerance.
