5-thiomethyl-2,2':5',2''-terthienyl | 118824-89-8

• 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
• 英文名称: 5-thiomethyl-2,2':5',2''-terthienyl
• 英文别名: 5-(methylthio)-2,2':5',2''-terthiophene；2-Methylsulfanyl-5-[5-(2-thienyl)-2-thienyl]thiophene；2-methylsulfanyl-5-(5-thiophen-2-ylthiophen-2-yl)thiophene
• CAS: 118824-89-8
• 化学式: C₁₃H₁₀S₄
• 分子量: 294.486
• InChiKey: GJWQKSIVZGJTII-UHFFFAOYSA-N

物化性质

• 熔点：
  86-89 °C
• 沸点：
  424.7±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium thioacyanate 、 5-thiomethyl-2,2':5',2''-terthienyl 在 溴 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以85%的产率得到[5-[5-(5-Methylsulfanylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl] thiocyanate
  参考文献：
  名称：

  部分双环[2.2.2]辛烯环和甲硫基封端的低聚噻吩硫醇盐保护的金纳米粒子的合成和导电性能。

  摘要：

  设计并合成了被双环[2.2.2]辛烯（BCO）单元部分退火的甲硫基封端的噻吩1a和季噻吩2a的硫醇盐保护的金纳米颗粒（AuNP）。还合成了覆盖有未退火的对噻吩3a的AuNP，以进行比较。通过吸收光谱和透射电子显微镜（TEM）测量证实了AuNP的形成。由于通过核心到核心隧穿的传导，AuNP-1a –和AuNP-3a –薄膜的电导率中等（〜10 –3 S cm –1），而AuNP-2a –胶片非常低（<10 –6 S cm –1）。TEM分析和DFT计算表明，AuNP-2a –薄膜的低电导率是由于两个空间要求较高的BCO单元之间的较大颗粒分离距离所致。重要的是，用碘蒸气掺杂之后，在的电导率的增强的AuNP-1A -和的AuNP-3A -只有4-和10倍，分别。与之形成鲜明对比，的导电性的AuNP-2A -后我2掺杂增加了超过10 4-折叠。后者的电导率可与先前报道的通过寡聚噻吩直接连接的AuN

  DOI：

  10.1021/cm501438j
• 作为产物：
  描述：

  2-噻吩硼酸 、 5-Iodo-5'-(methylthio)-2,2'-bithiophene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 以99%的产率得到5-thiomethyl-2,2':5',2''-terthienyl
  参考文献：
  名称：

  Microwave-Assisted Synthesis of Thiophene Fluorophores, Labeling and Multilabeling of Monoclonal Antibodies, and Long Lasting Staining of Fixed Cells

  摘要：

  We report the expedient microwave-assisted synthesis of thiophene based 4-sulfo-2,3,5,6,tetrafluorophenyl esters whose molecular structure was engineered to achieve blue to red bright fluorescence. The reactivity toward monoclonal antibodies of the newly synthesized fluorophores was analyzed in comparison with that of the corresponding A succinimidyl esters. Single-fluorophore and multiple-fluorophore labeled antibodies were easily prepared with both types of esters. Multiple-fluorophore labeling with blue and orange emitting fluorophores resulted in white fluorescent antibodies. Thiophene based fluorophores displayed unprecedented fluorescence stability in immunostaining experiments. First-principles TD-DFT theoretical calculations helped us to interpret the behavior of fluorescence emission in different environments.

  DOI：

  10.1021/ja902416s

文献信息

• Chiral control
  申请人：WAVE LIFE SCIENCES LTD.

  公开号：US10590413B2

  公开（公告）日：2020-03-17

  The present invention relates to chirally controlled oligonucleotides, chirally controlled oligonucleotide compositions, and the method of making and using the same. The invention specifically encompasses the identification of the source of certain problems with prior methodologies for preparing chiral oligonucleotides, including problems that prohibit preparation of fully chirally controlled compositions, particularly compositions comprising a plurality of oligonucleotide types. In some embodiments, the present invention provides chirally controlled oligonucleotide compositions. In some embodiments, the present invention provides methods of making chirally controlled oligonucleotides and chirally controlled oligonucleotide compositions.

  本发明涉及手性受控寡核苷酸、手性受控寡核苷酸组合物以及制作和使用方法。本发明具体包括确定先前制备手性寡核苷酸方法中某些问题的根源，包括禁止制备完全手性控制的组合物，特别是包含多种寡核苷酸类型的组合物的问题。在某些实施方案中，本发明提供了手性控制的寡核苷酸组合物。在一些实施方案中，本发明提供了制作手性控制寡核苷酸和手性控制寡核苷酸组合物的方法。
• Synthesis and characterization of alkyl-, halo- and hetero-substituted derivatives of the potent phototoxin α-terthienyl
  作者：Anita Mac Eachern、Chantal Soucy、Leonard C. Leitch、John T. Arnason、Peter Morand

  DOI：10.1016/s0040-4020(01)81692-6

  日期：1988.1
• EACHERN, ANITA MAC;SOUCY, CHANTAL;LEITCH, LEONARD C.;ARNASON, JOHN T.;MOR+, TETRAHEDRON, 44,(1988) N 9, 2403-2412
  作者：EACHERN, ANITA MAC、SOUCY, CHANTAL、LEITCH, LEONARD C.、ARNASON, JOHN T.、MOR+

  DOI：——

  日期：——
• Microwave-Assisted Synthesis of Thiophene Fluorophores, Labeling and Multilabeling of Monoclonal Antibodies, and Long Lasting Staining of Fixed Cells
  作者：Massimo Zambianchi、Francesca Di Maria、Antonella Cazzato、Giuseppe Gigli、Manuel Piacenza、Fabio Della Sala、Giovanna Barbarella

  DOI：10.1021/ja902416s

  日期：2009.8.12

  We report the expedient microwave-assisted synthesis of thiophene based 4-sulfo-2,3,5,6,tetrafluorophenyl esters whose molecular structure was engineered to achieve blue to red bright fluorescence. The reactivity toward monoclonal antibodies of the newly synthesized fluorophores was analyzed in comparison with that of the corresponding A succinimidyl esters. Single-fluorophore and multiple-fluorophore labeled antibodies were easily prepared with both types of esters. Multiple-fluorophore labeling with blue and orange emitting fluorophores resulted in white fluorescent antibodies. Thiophene based fluorophores displayed unprecedented fluorescence stability in immunostaining experiments. First-principles TD-DFT theoretical calculations helped us to interpret the behavior of fluorescence emission in different environments.
• Synthesis and Conductive Properties of Gold Nanoparticles Protected by Partially Bicyclo[2.2.2]octene-Annelated and Methylthio End-Capped Oligothiophene Thiolates
  作者：Masaki Tateno、Masayoshi Takase、Tohru Nishinaga

  DOI：10.1021/cm501438j

  日期：2014.6.24

  Gold-nanoparticles (AuNPs) protected by thiolates of methylthio end-capped terthiophene 1a and quaterthiophene 2a partially annelated with bicyclo[2.2.2]octene (BCO) unit(s) were designed and synthesized. AuNP covered with nonannelated terthiophene 3a was also synthesized for comparison. The formation of the AuNPs was confirmed by absorption spectra and transmission electron microscopy (TEM) measurements

  设计并合成了被双环[2.2.2]辛烯（BCO）单元部分退火的甲硫基封端的噻吩1a和季噻吩2a的硫醇盐保护的金纳米颗粒（AuNP）。还合成了覆盖有未退火的对噻吩3a的AuNP，以进行比较。通过吸收光谱和透射电子显微镜（TEM）测量证实了AuNP的形成。由于通过核心到核心隧穿的传导，AuNP-1a –和AuNP-3a –薄膜的电导率中等（〜10 –3 S cm –1），而AuNP-2a –胶片非常低（<10 –6 S cm –1）。TEM分析和DFT计算表明，AuNP-2a –薄膜的低电导率是由于两个空间要求较高的BCO单元之间的较大颗粒分离距离所致。重要的是，用碘蒸气掺杂之后，在的电导率的增强的AuNP-1A -和的AuNP-3A -只有4-和10倍，分别。与之形成鲜明对比，的导电性的AuNP-2A -后我2掺杂增加了超过10 4-折叠。后者的电导率可与先前报道的通过寡聚噻吩直接连接的AuN