2,5-bis(benzo[d]thiazol-2-yl)thiophene | 18013-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2,5-bis(benzo[d]thiazol-2-yl)thiophene
• 英文别名: 2,5-di(benzothiazolin-2-yl)thiophene；2,2'-thiophene-2,5-diyl-bis-benzothiazole；2,5-Di-(2-benzothiazolyl)thiophen；Thiophen；2-[5-(1,3-benzothiazol-2-yl)thiophen-2-yl]-1,3-benzothiazole
• CAS: 18013-43-9
• 化学式: C₁₈H₁₀N₂S₃
• 分子量: 350.489
• InChiKey: XKWQGJSPBYTEDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  二(氰基苯)二氯化钯 、 2,5-bis(benzo[d]thiazol-2-yl)thiophene 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Reaction of 2,5-(Dibenzothiazolin-2-yl)thiophene with Some Metal Ions

  摘要：

  DOI：

  10.1016/s0277-5387(00)87213-7
• 作为产物：
  描述：

  2,5-(dibenzothiazolin-2-yl)thiophene 在 air 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以100%的产率得到2,5-bis(benzo[d]thiazol-2-yl)thiophene
  参考文献：
  名称：

  Spectroscopic differences between heterocyclic benzothiazoline, -thiazole and imine containing ligands and comparison of the Co and Cu pyridine benzothiazole and imine complexes

  摘要：

  Five heterocyclic benzothiazoline and -thiazole analogs have been synthesized and characterized by H-1 NMR and IR spectroscopy. The analogs fall into two different classes, (a) those which contain one benzothiazoline group adjacent to the heterocyclic ring system (starting with 2-pyridinecarboxaldehyde, 2-thiophenecarboxaldehyde or 2-furaldehyde), and (b) those which have two benzothiazoline substituents (starting with 2,6-pyridinecarboxaldehyde and 2,5-thiohenecarboxaldehyde). In addition, the imine containing ligands, bis-2-[(pyridin-2-ylmethylene)-imino]-benzenethiol disulfide (PyIS)(2) and bis-2-[(thiophen-2-ylmethylene)-imino]-benzenethiol disulfide(ThIS)(2), were prepared starting with the disulfide of 2-aminothiophenol. Each species has been characterized by H-1 NMR and IR spectroscopies. Ligation reactions with 2-(2-pyridyl) benzothiazoline (Py(Bt)) and Cu(OAc)(2)center dot 1H(2)O resulted in the formation of a dinuclear species containing two copper ions, two ligand frames and two acetate groups, [Cu(PyA-S)( OAc)](2) (1). Both copper ions are five-coordinate and bonded to one monodentate acetate, one ligand frame (NNS) and one bridging thiolate. Ligation reaction with 2-(2-pyridyl) benzothiazole (Py(oBt)) and CoCl2 center dot xH(2)O or Cu(BF4)(2)center dot xH(2)O resulted in the formation of a six-coordinate, octahedral Co(II) complex, cis-[Co(Py(oBt)(2)Cl-2] (2) and a five coordinate Cu(II) complex, [Cu(Py(oBt))(2)(OH2)](BF4) (3), respectively. All complexes have been characterized by X-ray crystallography as well as UV-Vis and IR spectroscopy. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.09.002

文献信息

• Synthesis and redox behaviour of highly conjugated bis(benzo-1,3-dithiole) and bis(benzothiazole) systems containing aromatic linking groups: model systems for organic metals
  作者：Martin R. Bryce、Edwin Fleckenstein、Siegfried Hünig

  DOI：10.1039/p29900001777

  日期：——

  The synthesis and electrochemical redox properties of a series of symmetrical, highly conjugated bis(benzo-1,3-dithiole) and bis(benzothiazole) derivatives (8)–(24) are described. The heterocyclic end-groups are linked by a conjugated framework that incorporates the following groups: (a) phenyl, (b) naphthyl, (c) thienyl, (d) biphenyl, (e) anthracenyl, and (f) benzanthracenyl. Compounds (13) and (16)–(19)

  描述了一系列对称的，高度共轭的双（苯并-1,3-二硫醇）和双（苯并噻唑）衍生物（8）–（24）的合成和电化学氧化还原性能。杂环端基通过结合有以下基团的共轭框架连接：（a）苯基，（b）萘基，（c）噻吩基，（d）联苯，（e）蒽基和（f）苯并蒽基。化合物（13）和（16）–（19）在循环伏安图中显示两个单电子氧化还原波，而化合物（8）–（12），（14），（15），（20），（21） ，（23）和（24）显示单二电子氧化还原波。这些分子的氧化还原电势可以与其中中心桥环为芳族的系统的氧化还原态的增加的稳定性相关。
• Converting Thioether Waste into Organic Semiconductors by Carbon–Sulfur Bond Activation
  作者：Ting Zhu、Longfeng Jiang、Ying Li、Zengqi Xie、Zijie Li、Lei Lv、Hao Chen、Zhiyuan Zhao、Lang Jiang、Benzhong Tang、Hui Huang

  DOI：10.1002/anie.201901274

  日期：2019.4

  A goal for human society is to convert organic waste into valuable materials. Herein, 2‐(methylthio)‐bezothiazole (MTBT), an important organic waste in urban runoff, was catalytically converted into a series of organic semiconductors through carbon–sulfur bond activation. The efficient conversion of various substrates with different aromatic moieties and reacting functional groups (tin and boron) proved

  人类社会的目标是将有机废物转化为有价值的材料。在这里，2-（甲硫基）-苯并噻唑（MTBT）是城市径流中的重要有机废物，通过碳硫键的活化被催化转化为一系列有机半导体。具有不同芳族基团和反应性官能团（锡和硼）的各种底物的有效转化证明了这种新颖的二芳基化Liebeskind-Srogl方法的普遍性。此外，所得的有机半导体在场效应晶体管和单元成像中显示出优异的性能。这一贡献为将有机废物转化为有价值的材料提供了一个极好的例子，并可能为利用广泛可用的芳族硫醚开辟新途径。
• Coplanarity driven fluorescence turn-on sensor for chromium(iii) and its application for bio-imaging
  作者：G. Balamurugan、S. Velmathi

  DOI：10.1039/c7pp00425g

  日期：2018.2

  New benzimidazole and benzothiazole derivatives (S1-S3) derived from thiophene-2,5-dicarboxalde-hyde and 5,5′-bipyridyldicarboxaldehyde with NSN/SSS/NN binding sites were tested against various cations and anions. S3 showed selectivity toward copper(II) ions among other cations under consideration with the colour change to pale yellow from colourless under aqueous medium. In the cases of S1 and S2, no colour change was observed. S1 alone showed selective fluorescence turn on for Cr(III) ions among other cations. S1 showed sensitivity towards Cr(III) with fluorescence change with bathochromic shift. The prominent fluorescence change of S1 with Cr(III) ions was applied to live cell imaging of HeLa cells.

  研究人员针对各种阳离子和阴离子对具有 NSN/SSS/NN 结合位点的噻吩-2,5-二甲醛和 5,5′-联吡啶二甲醛衍生的新苯并咪唑和苯并噻唑衍生物（S1-S3）进行了测试。在所考虑的其他阳离子中，S3 对铜（II）离子具有选择性，在水介质中颜色从无色变为淡黄色。而 S1 和 S2 则没有颜色变化。在其他阳离子中，只有 S1 对 Cr（III）离子显示出选择性荧光。S1 显示出对 Cr（III）的敏感性，其荧光变化具有浴色偏移。S1 在 Cr(III) 离子作用下的显著荧光变化被应用于 HeLa 细胞的活细胞成像。
• Room Temperature Anhydrous Suzuki–Miyaura Polymerization Enabled by C−S Bond Activation
  作者：Xuan Wen、Wenbin Xie、Yawen Li、Xiaoying Ma、Zhaoying Liu、Xiao Han、Kaikai Wen、Fengjiao Zhang、Yuze Lin、Qinqin Shi、Aidong Peng、Hui Huang

  DOI：10.1002/anie.202309922

  日期：2023.10.2

  cross-coupling reaction between (hetero)aryl boronic esters and aryl sulfides was explored, of which universality was exemplified with thirty small molecules and twelve alternating conjugated polymers. Mechanism studies revealed the importance of room temperature and anhydrous condition in reducing the homocoupling defects and enhancing the optoelectronic properties of the conjugated polymers.

  探索了（杂）芳基硼酸酯和芳基硫醚之间的无水室温 CAS-Suzuki-Miyaura 交叉偶联反应，其通用性以 30 种小分子和 12 种交替共轭聚合物为例。机理研究揭示了室温和无水条件在减少自偶联缺陷和增强共轭聚合物光电性能方面的重要性。
• Kornilov,M.Yu. et al., Soviet progress in chemistry, 1974, vol. 40, # 5, p. 52 - 54
  作者：Kornilov,M.Yu. et al.

  DOI：——

  日期：——