2,5-二溴噻吩-3-羧酸甲酯 | 89280-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2,5-二溴噻吩-3-羧酸甲酯
• 英文名称: methyl 2,5-dibromothiophene-3-carboxylate
• 英文别名: Methyl 2,5-dibromothiophene-3-carboxylate
• CAS: 89280-91-1
• 化学式: C₆H₄Br₂O₂S
• 分子量: 299.971
• InChiKey: VAOITIHBHNKQKO-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C(Solv: methanol (67-56-1))
• 沸点：
  284.0±35.0 °C(Predicted)
• 密度：
  2.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2,5-二溴噻吩-3-羧酸甲酯 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 17.5h， 生成 2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxylic acid
  参考文献：
  名称：

  Gold nanoparticle-templated assembly of oligothiophenes: preparation and film properties

  摘要：

  Terthiophene-appended gold nanoparticles were prepared by the reduction of AuCl4-(C8H17)(4)N+ with NaBH4 in the presence of bis[2,5-di(3-hexylthiophen-2-yl)thiophene-3-carboxyloxyhexanyl]disulfide. A hexagonal self-assembly of particles with gold core diameters (1.9 +/- 0.1 nm) was detected by high-angle annular dark-field scanning transmission electron microscopy. The electric conductivity of the iodine-doped film was 9.1 x 10(-6) S cm(-1), which was ascribable to the terthiophene-based inter-ligand pi-pi interactions. The Au/terthiophene hybrid spin-coated film consisted of a highly three-dimensional assembled structure of terthiophenes, as inferred from grazing-incidence small-angle X-ray scattering, indicating that such monodispersed and small-sized gold nanoparticles can serve as a template for this organization. In this study, a gold nanoparticle-templated assembly of oligothiophenes has been fabricated for proposing a method to develop tailor-made organizations of pi-conjugated oligomers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.032
• 作为产物：
  描述：

  2,5-二溴-3-噻吩甲酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2,5-二溴噻吩-3-羧酸甲酯
  参考文献：
  名称：

  Polymer solar cells fabricated with 4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b′]dithiophene and alkyl-substituted thiophene-3-carboxylate-containing conjugated polymers: Effect of alkyl side-chain in thiophene-3-carboxylate monomer on the device performance

  摘要：

  Four alkyl-substituted thiophene-3-carboxylate containing donor-acceptor (D-A) copolymers were designed, synthesized, and characterized. Thiophene-3-carboxylate was used as a weak electron acceptor unit in the copolymers to provide a deeper highest occupied molecular orbital (HOMO) level for obtaining a higher open-circuit voltage in polymer solar cells (PSCs). The resulting bulk heterojunction PSCs, made of the copolymers and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM), exhibited different short circuit currents (J(SC)s) and open-circuit voltages (V(OC)s), depending on the length of alkyl side-chain in the thiophene-3-carboxylate unit. Among all fabricated photovoltaic (PV) devices, PC2:PC71BM (1:1 wt. ratio) showed the highest efficiency with the highest Jsc of 10.5 mA/cm(2). Although PC5:PC71BM (1:1) displayed the highest V-OC of 0.93 V. the device efficiency was observed to be poor, which is due to poor nanophase segregation. This comparison shows that the side-chain of thiophene carboxylate in these copolymers plays a very important role in the device efficiency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2012.07.007

文献信息

• Poly(alkyl thiophene-3-carboxylates). Synthesis, properties and electroluminescence studies of polythiophenes containing a carbonyl group directly attached to the ring
  作者：Martin Pomerantz、Yang Cheng、Ramesh K. Kasim、Ronald L. Elsenbaumer

  DOI：10.1039/a902504i

  日期：——

  Improved synthetic methodology for poly(3-hexyl- and 3-octyloxycarbonylthiophene-2,5-diyl) (1a and 1b) is reported. n =6700 and 9400 ( w / n =2.5 and 3.2), λ max for fluorescence emission=600 and 610 nm and λ max for electroluminescence=600 and 615 nm, for 1a and 1b respectively. The 1 H NMR spectra required that pentads be considered to explain the spectra. That is the four nearest neighbours to a given ring influence the 1 H NMR spectrum. Electroluminescence efficiencies of 0.016% and 0.018% were observed for devices made from 1a and 1b, respectively. A bilayer device of ITO/poly(3-octylthiophene)/1b/Al emitted at 646 nm, the same wavelength where poly(3-octylthiophene) itself emits. The efficiency was low but was an order of magnitude greater than for poly(3-octylthiophene) itself. Regioregular (HH-TT) poly(4,4′-bis(hexyl- and octyloxycarbonyl)[2,2′-bithiophene]-5,5′-diyl) (3a and 3b) were also prepared via the Ullmann reaction and n =7900 and 11000 respectively. Films of 3a and 3b were yellow in color and showed λ max =377 and 381 nm respectively, about 55-80 nm blue shifted compared with 1a and 1b. This is due to the large rotational barrier in the HH dyads which reduces the effective conjugation length in 3a and 3b. 3a and 3b showed bright fluorescence and electroluminescence with emission of yellow light. Electroluminescence efficiencies were 8.5×10 –3 % and 4.7×10 –3 %, respectively.

  报道了聚（3-己基-和3-辛氧基羰基噻吩-2,5-二基）（1a和1b）的改进合成方法。1a和1b的聚合度分别为6700和9400（重均/数均聚合度=2.5和3.2），其荧光发射最大波长分别为600和610 nm，电致发光最大波长分别为600和615 nm。1H NMR光谱要求考虑五聚体来解释光谱，即特定环的四个最近邻对1H NMR光谱有影响。从1a和1b制备的器件的电致发光效率分别为0.016%和0.018%。ITO/聚（3-辛基噻吩）/1b/Al的双层器件在646 nm处发光，这与聚（3-辛基噻吩）本身的发光波长相同。虽然效率较低，但比聚（3-辛基噻吩）本身的发光效率高出一个数量级。还通过Ullmann反应制备了区域规整的（HH-TT）聚[4,4′-双（己基-和辛氧基羰基）[2,2′-联噻吩]-5,5′-二基]（3a和3b），聚合度分别为7900和11000。3a和3b的薄膜呈黄色，显示的最大吸收波长分别为377和381 nm，相比于1a和1b蓝移了约55-80 nm。这是由于HH二聚体中的高旋转能垒减少了3a和3b中的有效共轭长度。3a和3b表现出明亮的荧光和电致发光，发射黄色光。电致发光效率分别为8.5×10–3%和4.7×10–3%。
• POLYMER SEMICONDUCTORS CONTAINING ACRYLYL OR ACRYLYL-LIKE SIDE CHAIN AND THEIR DEVICES
  申请人：UNIVERSITY OF WATERLOO

  公开号：US20210384435A1

  公开（公告）日：2021-12-09

  The present disclosure provides for the development and applications of monomeric, oligomeric and/or polymeric semiconductor materials comprising a five-membered heteroaromatic unit (e.g., thiophene; furan; selenophene; etc.) that includes an acrylyl or an acrylyl-like (—C═C—CO—) side chain. The semiconductor materials can be used as organic semiconductors for use in electronic, optical, or optoelectronic devices such as organic thin film transistors and organic photovoltaics. The disclosed semiconductor materials (e.g., semiconducting polymer compounds) can be used as high performance semiconductors (e.g., for organic solar cells or organic photovoltaics (OPVs)), and the disclosed semiconductor materials can be used for other devices (e.g., organic thin film transistors (OTFTs) and sensors, etc.).

  本公开提供了单体、寡聚体和/或聚合物半导体材料的开发和应用，其中包括一个五元杂环芳基单元（例如噻吩；呋喃；硒杂噻吩等），其中包括一个丙烯酰基或类似丙烯酰基（—C═C—CO—）侧链。这些半导体材料可用作有机半导体，用于电子、光学或光电子设备，如有机薄膜晶体管和有机光伏器件。公开的半导体材料（例如半导体聚合物化合物）可用作高性能半导体（例如用于有机太阳能电池或有机光伏器件），公开的半导体材料可用于其他设备（例如有机薄膜晶体管和传感器等）。
• Organic surface modification using stable conducting materials
  作者：Christopher D. McTiernan、Sara A. Abbas、M'hamed Chahma

  DOI：10.1039/c2nj40366h

  日期：——

  Efficient immobilization methods of amino acids and organic molecules on conducting surfaces were achieved using stable conducting materials such as OBT-functionalized polyterthiophene that allows readily the incorporation of specific motifs on conducting and semi-conducting surfaces. The synthesis of the electropolymerizable monomer has been performed through the protection of the carboxylic acid, followed by a Stille cross coupling reaction, deprotection of the acid and esterification using HOBT (hydroxybenzotriazole) and EDC. The corresponding polymer of 5 (poly(5)–Pt) exhibits excellent stability on a platinum electrode as shown by cyclic voltammetry, which allows the introduction of several amino acids and organic molecules on the surface of the functionalized polymer. The modified surface (poly(6)–Pt) has been characterized by ATR-Infrared showing a carbonyl stretch corresponding to an amide of the amino acids.

  通过使用稳定导电材料，如经OBT功能化的聚噻吩，实现了氨基酸和有机分子在导电表面上的高效固定化方法，这种方法便于在导电和半导电表面上引入特定结构基元。通过保护羧酸、接着进行Stille交叉偶联反应、酸脱保护及利用HOBT（羟基苯并三唑）和EDC酯化，完成了电聚合单体的合成。该单体对应的聚合物5（聚合物5–铂）在铂电极上表现出优异的稳定性，如循环伏安法所示，允许在功能化聚合物表面引入多种氨基酸和有机分子。经修饰的表面（聚合物6–铂）通过ATR红外光谱表征，显示出对应于氨基酸酰胺的羰基伸缩振动。
• Nickel-Catalyzed Suzuki Polycondensation for Controlled Synthesis of Ester-Functionalized Conjugated Polymers
  作者：Yunyan Qiu、Joshua C. Worch、Andria Fortney、Chakicherla Gayathri、Roberto R. Gil、Kevin J. T. Noonan

  DOI：10.1021/acs.macromol.6b01006

  日期：2016.7.12

  provided guidance for the polymerization of the ester-substituted monomer. This is the first report of nickel-catalyzed Suzuki cross-coupling for catalyst-transfer polycondensation, and to further illustrate the versatility of this method, block and alternating copolymers with 3-hexylthiophene were synthesized. The presented protocol should serve as an entry point into the synthesis of other electron-deficient

  具有功能性侧链的共轭聚合物的受控合成非常重要，与它们的烷基取代对应物相比，提供具有增强的稳定性和可调性的明确定义的光电材料。在此，描述了使用可商购的镍预催化剂的酯官能化噻吩的链增长Suzuki缩聚。模型化合物的研究被用来确定合适的催化剂，这些实验为酯取代的单体的聚合提供了指导。这是用于催化剂转移缩聚反应的镍催化Suzuki交叉偶联的首次报道，并且为进一步说明该方法的多功能性，合成了具有3-己基噻吩的嵌段共聚物和交替共聚物。
• Regular conjugated terpolymers comprising two different acceptors and bithiophene donor in repeating group: Effect of strong and weak acceptors on semiconducting properties
  作者：Mai Ha Hoang、Jong-Soo Ahn、Duc Nghia Nguyen、Trinh Tung Ngo、Dae Hee Lee、Min Ju Cho、Dong Hoon Choi

  DOI：10.1002/pola.27979

  日期：2016.5.15

  Diketopyrrolopyrrole (DPP)‐based terpolymers—P(DPP‐TPyT) and P(DPP‐T3MTT)—bearing bithiophene donating groups and weak accepting units such as pyridine (Py) or methyl thiophene‐3‐carboxylate (3MT), in the polymer backbone, were successfully synthesized. Although the two polymers had similar physical and electrochemical properties, grazing incidence X‐ray diffraction patterns of P(DPP‐TPyT) and P(DPP‐T3MTT)

  聚二吡咯并吡咯（DPP）基三元共聚物P（DPP-TPyT）和P（DPP-T3MTT）-在聚合物中带有联噻吩供体基团和弱接受单元，例如吡啶（Py）或噻吩-3-羧酸甲酯（3MT）骨架，已成功合成。尽管这两种聚合物具有相似的物理和电化学性质，但在热退火膜中，P（DPP-TPyT）和P（DPP-T3MTT）的掠入射X射线衍射图分别显示出混合和边沿取向。因此，P（DPP-T3MTT）在薄膜晶体管中的空穴迁移率是P（DPP-TPyT）的两倍，P（DPP-T3MTT）和[6,6]-苯基-C71-的混合膜丁酸甲酯（PC 71 BM）在聚合物太阳能电池中显示出更好的功率转换效率。©2015 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学2016，54，1339年至1347年