160096-76-4Relevant academic research and scientific papers
Cross-Coupling Polymerization of Organosodium for Polythiophene Synthesis
Horie, Masaki,Inoue, Tomoki,Mori, Atsunori,Okano, Kentaro,Sakagami, Yuma,Yamamoto, Sonoka
supporting information, p. 3506 - 3510 (2021/11/12)
Treatment of 2-chloro-3-hexylthiophene with sodium 2,2,6,6-tetramethylpiperidin-1-yl (TMPNa) in hexane resulted in deprotonation at the 5-position to afford the thiophene-sodium species, whose formation was confirmed by quenching with iodine, leading to 2-chloro-3-hexyl-5-iodothiophene in 85% yield. Addition of a nickel catalyst bearing an N-heterocyclic carbene (NHC) to the thus-formed thiophene-sodium species in cyclopentyl methyl ether induced a cross-coupling polymerization at -20 °C. After the reaction mixture was stirred for 24 h, poly(3-hexylthiophen-2,5-diyl) was obtained in 56% yield. The average molecular weight Mn was revealed to be 9700, which was close to the theoretical molecular weight (M = 8500) on the basis of the monomer feed/catalyst loading ratio (2.0 mol %), and the molecular weight distribution was found to be 2.1.
Aggregation induced emission-emissive stannoles in the solid state
Lork, Enno,Ramirez Y Medina, Isabel-Maria,Rohdenburg, Markus,Staubitz, Anne
supporting information, p. 9775 - 9778 (2020/09/07)
The optoelectronic and structural properties of six stannoles are reported. All revealed extremely weak emission in solution at 295 K, but intensive fluorescence in the solid state with quantum yields (ΦF) of up to 11.1% in the crystal, and of up to 24.4% (ΦF) in the thin film.
Organic Dye and Dye-Sensitized Solar Cell
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Paragraph 0116; 0135-0140, (2018/02/10)
PURPOSE: An organic dye, photoelectric diode including the same and dye-sensitized solar battery are provided to have an absorbing band in long wavelength. CONSTITUTION: An organic dye is represented by chemical formula 1. A photoelectric diode includes porous oxide semiconductor membrane which includes the organic dye. A dye-sensitized solar cell comprises a first electrode, a second electrode which is formed on one side of the first electrode and includes a light absorptive layer, and electrolyte buried in a space between the first and second electrodes.
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
, 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.
Nanostructured thermosets containing π-conjugated polymer nanophases: Morphology, dielectric and thermal conductive properties
Li, Jingang,Cong, Houluo,Li, Lei,Zheng, Sixun
, p. 193 - 203 (2015/06/23)
The nanostructured thermosets containing poly(3-hexylthiophene) (P3HT) nanophases were prepared by incorporating poly(ε-caprolactone)-block-poly(3-hexylthiophene)-block-poly(ε-caprolactone) (PCL-b-P3HT-b-PCL) triblock copolymer into epoxy. The PCL-b-P3HT-b-PCL triblock copolymer was synthesized via the combination of the polycondensation of 2-bromo-3-hexyl-5-iodothiophene and the ring-opening polymerization of ε-caprolactone; it was characterized by means of 1H nuclear magnetic resonance spectroscopy (1H NMR), gel permeation chromatography (GPC) and differential scanning calorimetry (DSC). The morphologies of the nanostructured thermosets were investigated by means of transmission electron microscopy (TEM), small angle X-ray scattering (SAXS) and dynamic mechanical thermal analysis (DMTA). The results of small angle X-ray scattering (SAXS) showed that the P3HT nanophases were formed via self-assembly mechanism of the triblock copolymer in epoxy thermosets. Compared to control epoxy, the nanostructured thermosets containing the conjugated nanophases significantly displayed the enhanced dielectric constants. In the meantime, the thermal conductivity of the nanostructured thermosets was also enhanced and increased with increasing the content of P3HT nanophases.
Modulating crystallinity of poly(3-hexylthiophene) via microphase separation of poly(3-hexylthiophene)-polyisoprene block copolymers
Lim, Herman,Chao, Chi-Yang,Su, Wei-Fang
, p. 3269 - 3281 (2015/06/08)
A series of poly(3-hexylthiophene)-block-polyisoprene (P3HT-b-PI) diblock copolymers (DBCP) and polyisoprene-block-poly(3-hexylthiophene)-block-polyisoprene (PI-b-P3HT-b-PI) triblock copolymers (TBCP) with accurately controlled molecular architecture were synthesized via highly efficient coupling reaction between aldehyde end-functionalized P3HT and living anionic polyisoprene. The self-assembly behaviors, considering morphology and crystallinity, of the thermal annealed bulk samples of these DBCPs and TBCPs containing various PI content were systematically investigated. The DBCPs behaved very differently from most published P3HT BCP systems, showing elongated fibers with preserved crystallinity regardless of the PI fraction. More noteworthy, with PI fraction less than 40 wt %, the DBCPs exhibited parallel straight fibers longer than several micrometers accompanied by concurrent enhanced crystallinity. The unique microstructure of the DBCPs might originate from moderate microphase separation between P3HT and PI as well as high flexibility of PI to conduct the packing of P3HT. The TBCPs, by contrast, exhibited highly curved interdomain boundaries with significant depressed crystallinity, resembling P3HT diblock copolymers in the strong phase segregation regime, as more pronounced entanglement of the two terminal PI segments would restrict the movement of P3HT.
Influence of the bulkiness of the substituent on the aggregation and magnetic properties of poly(3-alkylthiophene)s
Peeters, Helmuth,Jivanescu, Mihaela,Stesmans, Andre,Pereira, Lino M. C.,Dillemans, Leander,Locquet, Jean-Pierre,Van Bael, Margriet J.,Persoons, Andre,Koeckelberghs, Guy
, p. 76 - 86 (2014/01/06)
A series of poly(3-alkylthiophene)s (P3ATs) (P1-P5) has been synthesized via a Ni(dppp)-mediated polymerization, varying the bulkiness of the alkyl side chains in order to investigate the influence of the bulkiness of the alkyl substituent on the aggregation and magnetic properties of P3ATs. UV-Vis spectroscopy, performed in solution as well as in film, shows that the stacking of the polymers becomes more complicated as the bulkiness of the side chains increases. Both the π-interactions and the planarization of the polymer chains are diminished. While aggregation is absent in poor solvent for the polymer with the most bulky side chains, aggregation was present in film, albeit slowed down. This behavior was also confirmed by X-ray diffraction (XRD) and differential scanning calorimetry (DSC) experiments. Electron spin resonance (ESR) measurements, performed at 300 K on powders, confirmed the trend of decreasing supramolecular order with increasing bulkiness of the side-chain. Magnetization measurements, performed at 5 and 300 K, are in line with our hypothesis on the influence of π-interactions and the fraction of planar polymer chains on the coercivity and saturation magnetization, respectively.
Amphiphilic poly(3-hexylthiophene)-based semiconducting copolymers for printing of polyelectrolyte-gated organic field-effect transistors
Laiho, Ari,Nguyen, Ha Tran,Sinno, Hiam,Engquist, Isak,Berggren, Magnus,Dubois, Philippe,Coulembier, Olivier,Crispin, Xavier
, p. 4548 - 4557 (2013/07/11)
Polyelectrolytes are promising electronically insulating layers for low-voltage organic field effect transistors. However, the polyelectrolyte- semiconductor interface is difficult to manufacture due to challenges in wettability. We introduce an amphiphilic semiconducting copolymer which, when spread as a thin film, can change its surface from hydrophobic to hydrophilic upon exposure to water. This peculiar wettability is exploited in the fabrication of polyelectrolyte-gated field-effect transistors operating below 0.5 V. The prepared amphiphilic semiconducting copolymer is based on a hydrophobic regioregular poly(3-hexylthiophene) (P3HT) covalently linked to a hydrophilic poly(sulfonated)-based random block. Such a copolymer is obtained in a three-step strategy combining Grignard metathesis (GRIM), atom transfer radical polymerization (ATRP) processes, and a postmodification method. The structure of the diblock copolymer was characterized using FT-IR, 1H NMR spectroscopy, and gel permeation chromatography (GPC).
Dual selectivity: Electrophile and nucleophile selective cross-coupling reactions on a single aromatic substrate
Heinrich, Annika C. J.,Thiedemann, Birk,Gates, Paul J.,Staubitz, Anne
supporting information, p. 4666 - 4669 (2013/10/08)
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.
A poly(3-hexylthiophene) block copolymer with macroscopically aligned hierarchical nanostructure induced by mechanical rubbing
Lim, Herman,Ho, Chun-Chi,Wu, Shang-Jung,Tsai, Hsin-Chieh,Su, Wei-Fang,Chao, Chi-Yang
supporting information, p. 9146 - 9148 (2013/09/24)
A highly ordered, uniformly aligned nanostructure with good crystallinity was first achieved on a P3HT block copolymer possessing a low weight fraction (19.4 wt%) of a flexible polyisoprene segment via a mechanical rubbing process without the use of solution based fabrication and thermal annealing. The attachment of the short polyisoprene segment to P3HT would significantly promote the main chain mobility to allow the orientation control of P3HT and of the self-assembled nanostructure by rubbing.
