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2-Bromo-3-hexylthiophene is a monomeric precursor that forms bromo-terminated polymers. It is synthesized by the bromination of hexylthiophene and is characterized as a colorless to yellow liquid.

69249-61-2

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69249-61-2 Usage

Uses

Used in Organic Synthesis:
2-Bromo-3-hexylthiophene is used as a key intermediate in the synthesis of end-capped regioregular poly(3-hexylthiophene), which is an important polymer in the field of organic electronics.
Used in High-Technology Applications:
2-Bromo-3-hexylthiophene is also used to synthesize well-defined head-to-tail-type oligothiophenes, which are utilized in a variety of high-technology applications, including organic light-emitting diodes (OLEDs). These oligothiophenes contribute to the development of advanced electronic devices and materials with improved performance and efficiency.

Check Digit Verification of cas no

The CAS Registry Mumber 69249-61-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,9,2,4 and 9 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 69249-61:
(7*6)+(6*9)+(5*2)+(4*4)+(3*9)+(2*6)+(1*1)=162
162 % 10 = 2
So 69249-61-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H15BrS/c1-2-3-4-5-6-9-7-8-12-10(9)11/h7-8H,2-6H2,1H3

69249-61-2 Well-known Company Product Price

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  • TCI America

  • (B3507)  2-Bromo-3-hexylthiophene  >98.0%(GC)

  • 69249-61-2

  • 5g

  • 1,340.00CNY

  • Detail
  • TCI America

  • (B3507)  2-Bromo-3-hexylthiophene  >98.0%(GC)

  • 69249-61-2

  • 25g

  • 3,790.00CNY

  • Detail
  • Alfa Aesar

  • (H56243)  2-Bromo-3-hexylthiophene, 98%   

  • 69249-61-2

  • 5g

  • 1092.0CNY

  • Detail
  • Alfa Aesar

  • (H56243)  2-Bromo-3-hexylthiophene, 98%   

  • 69249-61-2

  • 25g

  • 3750.0CNY

  • Detail
  • Aldrich

  • (691925)  2-Bromo-3-hexylthiophene  97%

  • 69249-61-2

  • 691925-1G

  • 766.35CNY

  • Detail
  • Aldrich

  • (691925)  2-Bromo-3-hexylthiophene  97%

  • 69249-61-2

  • 691925-5G

  • 2,027.61CNY

  • Detail

69249-61-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Bromo-3-hexylthiophene

1.2 Other means of identification

Product number -
Other names 2-bromo-3-hexylthiophene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:69249-61-2 SDS

69249-61-2Relevant articles and documents

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

, 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.

Push-pull thiophene-based small molecules with donor and acceptor units of varying strength for photovoltaic application: Beyond P3HT and PCBM

Boschi, Alex,Candini, Andrea,Di Maria, Francesca,Gazzano, Massimo,Lanzi, Massimiliano,Marinelli, Martina,Monti, Filippo,Pierini, Filippo,Salatelli, Elisabetta,Zanelli, Alberto,Zangoli, Mattia

supporting information, p. 11216 - 11228 (2021/09/15)

Here is reported an expedient synthesis implementing enabling technologies of a family of thiophene-based heptamers alternating electron donor (D) and acceptor (A) units in a D-A′-D-A-D-A′-D sequence. The nature of the peripheral A groups (benzothiadiazole vs. thienopyrrole-dione vs. thiophene-S,S-dioxide) and the strength of the donor units (alkyl vs. thioalkyl substituted thiophene ring) have been varied to finely tune the chemical-physical properties of the D-A oligomers, to affect the packing arrangement in the solid-state as well as to enhance the photovoltaic performances. The optoelectronic properties of all compounds have been studied by means of optical spectroscopy, electrochemistry, and density functional theory calculations. Electrochemical measurements and Kelvin probe force microscopy (KPFM) predicted a bifunctional behaviour for these oligomers, suggesting the possibility of using them as donor materials when blended with PCBM, and as acceptor materials when coupled with P3HT. Investigation of their photovoltaic properties confirmed this unusual characteristic, and it is shown that the performance can be tuned by the different substitution pattern. Furthermore, thanks to their ambivalent character, binary non-fullerene small-molecule organic solar cells with negligible values of HOMO and LUMO offsets were also fabricated, resulting in PCEs ranging between 2.54-3.96%. This journal is

Planar and twisted molecular structure leads to the high brightness of semiconducting polymer nanoparticles for NIR-IIa fluorescence imaging

Liu, Shunjie,Ou, Hanlin,Li, Yuanyuan,Zhang, Haoke,Liu, Junkai,Lu, Xuefeng,Kwok, Ryan T.K.,Lam, Jacky W.Y.,Ding, Dan,Tang, Ben Zhong

supporting information, p. 15146 - 15156 (2020/10/13)

Semiconducting polymer nanoparticles (SPNs) emitting in the second near-infrared window (NIR-II, 1000-1700 nm) are promising materials for deep-tissue optical imaging in mammals, but the brightness is far from satisfactory. Herein, we developed a molecular design strategy to boost the brightness of NIR-II SPNs: structure planarization and twisting. By integration of the strong absorption coefficient inherited from planar π-conjugated units and high solid-state quantum yield (φPL) from twisted motifs into one polymer, a rise in brightness was obtained. The resulting pNIR-4 with both twisted and planar structure displayed improved φPL and absorption when compared to the planar polymer pNIR-1 and the twisted polymer pNIR-2. Given the emission tail extending into the NIR-IIa region (1300-1400 nm) of the pNIR-4 nanoparticles, NIR-IIa fluorescence imaging of blood vessels with enhanced clarity was observed. Moreover, a pH-responsive poly(β-amino ester) made pNIR-4 specifically accumulate at tumor sites, allowing NIR-IIa fluorescence image-guided cancer precision resection. This study provides a molecular design strategy for developing highly bright fluorophores.

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.

Single-material organic solar cells with fully conjugated electron-donor alkoxy-substituted bithiophene units and electron-acceptor benzothiadiazole moieties alternating in the main chain

Di Maria, Francesca,Lanzi, Massimiliano,Liscio, Andrea,Marinelli, Martina,Salatelli, Elisabetta,Zanelli, Alberto,Zangoli, Mattia

supporting information, p. 4124 - 4132 (2020/04/15)

Main chain conjugated linear polymers, constituted by alternating electron-donor (D) and-acceptor (A) moieties, have been prepared with the aim of testing their performances as photoactive components in single material organic solar cells (SMOSCs). The D moiety is constituted by bithiophene co-units bearing in position 3 of the thiophene ring a hexyloxy, a hexyloxymethyl or a hexyl group, while the A moiety is represented by the benzothiadiazole group. The D-A polymers were obtained in high yield through the poorly demanding oxidative FeCl3 polymerization process-starting, respectively, from the related precursors 4,7-bis(3-hexyloxythiophen-2-yl)benzo[c][2,1,3]thiadiazole, 4,7-bis[3-(6-methoxyhexyl)thiophen-2-yl]benzo[c][2,1,3]thiadiazole and 4,7-bis(3-hexylthiophen-2-yl)benzo[c][2,1,3]thiadiazole-with low dispersity indexes, close to the monodisperse state, after fractionation with methanol. The materials have been thoroughly characterized for their physical and structural properties and then tested for photoconversion efficiency in SMOSCs by using different deposition procedures of the photoactive component. In agreement with Kelvin probe force microscopy (KPFM) measurements, the best photovoltaic performance was observed for the polymer based on conjugated 3-alkoxythiophene and benzothiadiazole moieties, achieving significant photocurrents for this type of fully conjugated alternating D-A structure (Jsc = 2.63-3.72 mA cm-2).

Synthesis of side-chain regioregular and main-chain alternating poly(bichalcogenophene)s and an ABC-type periodic poly(terchalcogenophene)

Cheng, Kuang-Yi,Cheng, Yen-Ju,Huang, Sheng-Cih,Lai, Yu-Ying,Liang, Wei-Wei,Liu, Huai-Hsuan,Su, Yen-Chen,Yang, Hau-Ren

, p. 3836 - 3844 (2020/04/27)

Three unsymmetrical diiodobichalcogenophenes SSeI2, STeI2, and SeTeI2 and a diiodoterchalcogenophene SSeTeI2 were prepared. Grignard metathesis of SSeI2, STeI2, SeTeI2, and SSeTeI2 occurred regioselectively at the lighter chalcogenophene site because of its relatively lower electron density and less steric bulk. Nickel-catalyzed Kumada catalyst-transfer polycondensation of these Mg species provided a new class of side-chain regioregular and main-chain AB-type alternating poly(bichalcogenophene)s - PSSe, PSTe, and PSeTe - through a chain-growth mechanism. The ring-walking of the Ni catalyst from the lighter to the heavier chalcogenophene facilitated subsequent oxidative addition, thereby suppressing the possibility of chain-transfer or chain-termination. More significantly, the Ni catalyst could walk over the distance of three rings (ca. 1 nm) - from a thiophene unit via a selenophene unit to a tellurophene unit - to form PSSeTe, the first ABC-type regioregular and periodic poly(terchalcogenophene) comprising three different types of 3-hexylchalcogenophenes.

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).

Synthesis and Characterization of Diferrocenyl Conjugates: Varying π-Conjugated Bridging Ligands and its Consequence on Electrochemical Communication

Roy, Sourav Saha,Patra, Sanjib K.

supporting information, p. 2193 - 2201 (2019/04/17)

Organometallic wire-like complexes with ferrocenyl termini, conjugated with one and two units of thienylethynyl (M1 and M2) and thienyl (M3 and M4) groups, have been synthesized with a general formula of [Fc-C≡C-(Th-C≡C)1-2-Fc] and [Fc-(Th)1-2-Fc] (Fc = ferrocenyl, Th = thienyl) respectively. The diferrocenyl organometallic complexes have been characterized by various spectroscopic tools such as multinuclear NMR, FTIR, elemental analysis, and mass spectrometry. The electrochemical properties of these compounds have been investigated by cyclic (CV) and differential pulse voltammetry (DPV). The single reversible oxidation wave in diferrocenyl complexes with thienylethynyl spacers (M1 and M2) indicates the absence of intramolecular electrochemical communication between the two ferrocenyl termini. Interestingly, the diferrocenyl complexes with one and two thienyl spacers (M3 and M4) show two successive reversible one-electron oxidation waves, indicating electronic coupling between the two ferrocenyl (Fc) termini. The potential difference (ΔE1/2) between the two redox centers is 160 mV and 130 mV, respectively, with the corresponding comproportionation constants (Kc) of 6.2 × 102 and 1.5 × 102. Upon mono-oxidation of M3 by [Cp2Fe][BF4], a broad and weak intervalence charge-transfer (IVCT) transition is observed in the NIR region of 1200–2200 nm.

ORGANIC SEMICONDUCTOR COMPOUND HAVING LOW BAND-GAP, AND TRANSISTOR AND ELECTRONIC DEVICE INCLUDING THE SAME

-

Paragraph 0178; 0184-0189, (2018/05/03)

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

Molecular engineering of face-on oriented dopant-free hole transporting material for perovskite solar cells with 19% PCE

Rakstys, Kasparas,Paek, Sanghyun,Gao, Peng,Gratia, Paul,Marszalek, Tomasz,Grancini, Giulia,Cho, Kyung Taek,Genevicius, Kristijonas,Jankauskas, Vygintas,Pisula, Wojciech,Nazeeruddin, Mohammad Khaja

supporting information, p. 7811 - 7815 (2017/07/13)

Through judicious molecular engineering, novel dopant-free star-shaped D-π-A type hole transporting materials coded KR355, KR321, and KR353 were systematically designed, synthesized and characterized. KR321 has been revealed to form a particular face-on organization on perovskite films favoring vertical charge carrier transport and for the first time, we show that this particular molecular stacking feature resulted in a power conversion efficiency over 19% in combination with mixed-perovskite (FAPbI3)0.85(MAPbBr3)0.15. The obtained 19% efficiency using a pristine hole transporting layer without any chemical additives or doping is the highest, establishing that the molecular engineering of a planar donor core, π-spacer and periphery acceptor leads to high mobility, and the design provides useful insight into the synthesis of next-generation HTMs for perovskite solar cells and optoelectronic applications.

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