1693-86-3Relevant articles and documents
Synthesis and photovoltaic properties of low-bandgap 4,7-dithien-2-yl-2,1, 3-benzothiadiazole-based poly(heteroarylenevinylene)s
Wen, Shanpeng,Pei, Jianing,Li, Pengfei,Zhou, Yinhua,Cheng, Weidong,Dong, Qingfeng,Li, Zaifang,Tian, Wenjing
, p. 2715 - 2724 (2011)
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.
Physical, mechanical, and conductivity properties of poly(3-hexylthiophene) -montmorillonite clay nanocomposites produced by the solvent casting method
Kuila, Biplab K.,Nandi, Arun K.
, p. 8577 - 8584 (2004)
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.
Regiospecific Synthesis of 3-Alkylfuranes and 3-Alkylthiophenes via Organoboranes
Akimoto, Itaru,Sano, Masahiro,Suzuki, Akira
, p. 1587 - 1588 (1981)
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.
Redox-Divergent Construction of (Dihydro)thiophenes with DMSO
Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang
supporting information, p. 24284 - 24291 (2021/10/08)
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.
Efficient Pd-Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents
Dilchert, Katharina,Gessner, Viktoria H.,Gro?johann, Angela,Rodstein, Ilja,Scherpf, Thorsten,Steinert, Henning,Tappen, Jens
supporting information, p. 20596 - 20603 (2020/09/09)
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.
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)
Giri, Dipanjan,Patra, Sanjib K.
supporting information, p. 14469 - 14480 (2020/11/09)
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.
Conductive triethylene glycol monomethyl ether substituted polythiophenes with high stability in the doped state
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.
, p. 1079 - 1086 (2019/03/21)
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).
Syntheses and photovoltaic properties of 6-(2-thienyl)-4H-thieno[3,2-b]indole based conjugated polymers containing fluorinated benzothiadiazole
Jeong, Ina,Chae, Sangmin,Yi, Ahra,Kim, Juae,Chun, Ho Hwan,Cho, Jung Hyeong,Kim, Hyo Jung,Suh, Hongsuk
, p. 115 - 125 (2016/12/30)
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).
The Discovery of Citral-Like Thiophenes in Fried Chicken
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.
, p. 5690 - 5699 (2017/07/24)
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.
Synthesis of poly(thiophene-alt-pyrrole) from a difunctionalized thienylpyrrole by Kumada polycondensation
He, Lu-Ying,Urrego-Riveros, Sara,Gates, Paul J.,N?ther, Christian,Brinkmann, Maren,Abetz, Volker,Staubitz, Anne
supporting information, p. 5399 - 5406 (2015/07/15)
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.
