3,5-二溴-2-(5-溴噻吩-2-基)噻吩 | 117969-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 中文名称: 3,5-二溴-2-(5-溴噻吩-2-基)噻吩
• 英文名称: 3,5,5'-tribromo-2,2'-bithiophene
• 英文别名: 3,5,5’-tribromo-2,2’-bithiophene；3,5,5′-tribromo-2,2′-bithiophene；3,5-dibromo-2-(5-bromothiophen-2-yl)thiophene
• CAS: 117969-89-8
• 化学式: C₈H₃Br₃S₂
• 分子量: 402.956
• InChiKey: XNYBUDGYYPPKTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-二溴-2-(5-溴噻吩-2-基)噻吩 在 盐酸 、 正丁基锂 、 溶剂黄146 、 锌 作用下， 以 乙醚 、 乙醇 、 正己烷 、 水 为溶剂， 反应 22.0h， 生成 (2,2'-bithiophenyl-3-yl)diphenylmethanol
  参考文献：
  名称：

  Synthesis and optical properties of poly(tetramethylsilarylenesiloxane) derivative bearing diphenylcyclopentadithiophene moiety

  摘要：

  The thermal and optical properties of a novel diphenylcyclopentadithiophene-based poly(-tetramethylsilarylenesiloxane) derivative (P1), which was prepared via polycondensation of a novel disilanol monomer, i.e., 2,6-bis(dimethylhydroxysilyl)-4,4-diphenylcyclopentadithiophene (M1), were investigated. P1 exhibited good solubility in common organic solvents, such as benzene, toluene, chloroform, dichloromethane and THF at ambient temperature. The glass transition temperature (T-g) of P1 was determined by differential scanning calorimetry to be 109 degrees C. No melting temperature (T-m) of P1 was observed, indicating the obtained P1 was an amorphous polymer. The temperature at 5% weight loss (T-d5) of P1 was 454 degrees C, indicating the rather good thermostability of P1. Bathochromic and hyperchromic effects were observed in the absorption and fluorescence spectra by introducing dimethylsilyl substituents onto 4,4-diphenylcyclopentadithiophene skeleton. The fluorescence quantum yields (Phi(FS)) of M1 and P1 in chloroform were determined to be 0.36 and 0.39, respectively. It was revealed that M1 and P1 exhibited the higher fluorescence intensity than diphenylcyclopentadithiophene owing to the cooperative effects of the introduction of diphenyl groups onto spiro carbon of cyclopentadithiophene as well as dimethylsilyl moieties onto 2- and 6-position of cyclopentadithiophene skeleton. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2014.10.048
• 作为产物：
  描述：

  2,2'-联二噻吩 在 lead(IV) tetraacetate 、 lithium bromide 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 3,5-二溴-2-(5-溴噻吩-2-基)噻吩
  参考文献：
  名称：

  2,2'-联噻吩的一锅、区域选择性连续多卤化

  摘要：

  证明了 2,2'-联噻吩 (1) 的一锅区域选择性连续多卤化。在室温或回流条件下，在四乙酸铅的存在下，将化合物 1 用溴化锂、氯化锂和/或碘化锂等卤化锂连续卤化，得到 5-溴（或氯）-5'-碘（或氯)-, 3-溴(或氯)-5,5'-二溴(或二氯、二碘)-, 3,3'-二溴-(或二氯)-5,5'-二碘(或二溴、二氯) -, 和 3,3',5-三溴（或三氯）-5'-碘（或溴）-2,2'-联噻吩。值得注意的是，该工艺为一锅连续多卤化提供了一种区域选择性方法，其产率和选择性也高于分步和并发卤化方法。

  DOI：

  10.1002/ejoc.201300379

文献信息

• Selective Halogenation of Bithiophenes Using 2-Halopyridazin-3(2H)-ones ­under Ambient Conditions
  作者：Jong Park、Yong-Jin Yoon、Kwang-Ju Jung、Seung Kang、Ju-Eun Won、Song-Eun Park、Ki Park、Sang-Gyeong Lee

  DOI：10.1055/s-0028-1087536

  日期：2009.2

  2,2′-Bithiophene and halogenated-2,2′-bithiophenes were halogenated with 2-halo-4,5-dichloropyridazin-3(2H)-one in the presence of zinc halide to give selectively the corresponding dihalo-, trihalo-, and tetrahalo-2,2′-bithiophenes involving the same or different halogens in excellent yields, respectively.

  2,2'-二噻吩和卤代-2,2'-二噻吩在氯化锌存在下与2-卤-4,5-二氯吡啶噁噻唑-3(2H)-酮卤化，选择性地生成相应的二卤、三卤和四卤-2,2'-二噻吩，涉及相同或不同的卤素，且产率优异。
• Synthesis and Photovoltaic Applications of a 4,4′-Spirobi[cyclopenta[2,1-<i>b</i>;3,4-<i>b</i>′]dithiophene]-Bridged Donor/Acceptor Dye
  作者：Gianluca Pozzi、Simonetta Orlandi、Marco Cavazzini、Daniela Minudri、Lorena Macor、Luis Otero、Fernando Fungo

  DOI：10.1021/ol402420w

  日期：2013.9.20

  A new donor/acceptor (D–A) spiro dye (SCPDT1) featuring two bithiophene units, connected through an sp3-hybridized carbon atom, was prepared by a multistep synthetic sequence involving the convenient assembly of the spiro system under mild catalytic conditions. The photocurrent spectrum of dye-sensitized solar cells incorporating SCPDT1 covers the spectral region ranging from 350 to 700 nm and reaches

  一种新的供体/受体（DA）螺旋染料（SCPDT1），具有两个通过SP 3-杂化碳原子连接的联噻吩单元，是通过多步合成序列制备的，该过程涉及在温和的催化条件下方便地组装螺旋系统。装有SCPDT1的染料敏化太阳能电池的光电流光谱覆盖350至700 nm的光谱范围，并在420-560 nm范围内达到约80％的最大最大值。获得了高达6.02％的功率转换效率。
• Polymer, method of preparing the same, and organic optoelectric device including the same
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY

  公开号：US09847489B1

  公开（公告）日：2017-12-19

  Provided are a novel polymer, a method of preparing the same, and an organic semiconductor device including the same. According to the present invention, the fluorine content-controlled polymer is employed in an organic active layer, thereby providing an organic optoelectric device representing improved power conversion efficiency (PCE).

  提供了一种新型聚合物，一种制备该聚合物的方法，以及包括该聚合物的有机半导体器件。根据本发明，在有机活性层中采用了氟含量可控的聚合物，从而提供了一种代表提高功率转换效率（PCE）的有机光电器件。
• Ng, S. C.; Chan, H. S. O.; Huang, H. H., Journal of Chemical Research, Miniprint, 1996, # 5, p. 1285 - 1294
  作者：Ng, S. C.、Chan, H. S. O.、Huang, H. H.、Seow, R. S. H.

  DOI：——

  日期：——
• US9847489B1
  申请人：——

  公开号：US9847489B1

  公开（公告）日：2017-12-19