3,4-bis(trimethylsilylethynyl)thiophene | 138354-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3,4-bis(trimethylsilylethynyl)thiophene
• 英文别名: trimethyl-[2-[4-(2-trimethylsilylethynyl)thiophen-3-yl]ethynyl]silane
• CAS: 138354-59-3
• 化学式: C₁₄H₂₀SSi₂
• 分子量: 276.55
• InChiKey: BTEHTBFAYUJOFF-UHFFFAOYSA-N

物化性质

• 沸点：
  301.2±42.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-bis(trimethylsilylethynyl)thiophene 在 trimethylamine N-oxide 、 tetrabutylammonium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 生成 3-[Co2(CO)4(μ-bis(diphenylphosphino)amine)(μ2-η2-(HC2))]-4-ethynylthiophene
  参考文献：
  名称：

  The effect of thiophene ring substitution position on the properties and electrochemical behaviour of alkyne–dicobaltcarbonylthiophene complexes

  摘要：

  A large number of Co-2(CO)(6)- and Co-2(CO)(4)(L-L)-substituted alkyne complexes (L-L = dppa and dmpm) have been prepared, characterized and studied by cyclic and square-wave voltammetry. In this paper we report a comparative electrochemical study of 2,5-, 2,4-, 3,4- and 2,3-bis(trimethylsilylethynyl) thiophene dicobalt substituted alkyne complexes, in order to evaluate the extent of the electronic interaction between the "Co2C2" redox centres depending on the position of the alkynyl substituent on the thiophene ring. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.08.005
• 作为产物：
  描述：

  3,4-二碘噻吩 、 三甲基乙炔基硅 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 反应 22.0h， 以83%的产率得到3,4-bis(trimethylsilylethynyl)thiophene
  参考文献：
  名称：

  重新审视脱氢噻吩 [12] 环烯：合成、电子性质和芳香性

  摘要：

  使用组合的实验和理论方法重新审视乙炔桥连的六氢三噻吩并 [12] 环烯( HDTA )的芳香性和电子特性。此外，我们尝试合成丁二炔桥连的八氢双噻吩 [12] 环烯( ODTA )。虽然通过核磁共振光谱、质谱和紫外可见吸收测量表明ODTA的形成，但由于其不稳定性，我们分离ODTA的尝试没有成功。相反，它们的结构和能量特性是使用 DFT 计算来预测的。HDTA异构体，其中噻吩环与 12 元环稠合的位置不同（b - 与c -位置）显示出它们的 HOMO-LUMO 能隙（E Gap）的明显差异。根据噻吩环的融合位置，ODTA也显示出较大的E间隙差异。噻吩环的二烯特性显着改变了电子性质；即，在HDTA和ODTA的异构体之间观察到了 >1 eV 的E Gap差异。HDTA和ODTA的理论评估表明b - 和c之间的局部芳香性/反芳香性存在显着差异-异构体。b-异构体的 12 元环的抗芳香性减弱，而c-异

  DOI：

  10.1021/acs.joc.1c00888

文献信息

• Using the FpXylBH₂•SMe₂ reagent for the regioselective synthesis of cyclic bis(alkenyl)boranes
  作者：Karel Škoch、Constantin G. Daniliuc、Gerald Kehr、Gerhard Erker

  DOI：10.1039/d0cc05230b

  日期：——

  The reactive borane reagent FpXylBH2•SMe2 was prepared from 1,4-bis(trifluoromethyl)benzene by treatment with n-BuLi, followed by H3B·SMe2 and subsequent removal of hydride. It undergoes a regioselective hydroboration reaction with 1,2-bis(trimethylsilylethynyl)benzene to give the “dimeric” product 13a featuring a conjugated 14-membered core heterocyclic structure that contains a pair of FpXylB units

  硼烷反应试剂FpXylBH 2 •SMe 2由1,4-双（三氟甲基）苯经正丁基锂处理，再经H 3 B·SMe 2和随后的氢化物处理制得。其与1，2-双（三甲基甲硅烷基乙炔基）苯进行区域选择性的氢硼化反应，得到具有包含一对FpXylB单元的共轭14元核心杂环结构的“二聚”产物13a。
• Heteroaryl-linked norbornadiene dimers with redshifted absorptions
  作者：Mads Mansø、Behabitu Ergette Tebikachew、Kasper Moth-Poulsen、Mogens Brøndsted Nielsen

  DOI：10.1039/c8ob01470a

  日期：——

  Development of Molecular Solar Thermal (MOST) systems for harvesting and storing solar energy is based on molecular photoswitches that undergo photoisomerizations to metastable isomers. One challenge is to achieve low-molecular weight molecules that absorb at sufficiently long wavelengths to match the solar spectrum. Here we show that this can be achieved by linking two norbornadiene (NBD) photoswitches

  用于收获和储存太阳能的分子太阳能热（MOST）系统的开发基于分子光开关，该光开关经历了光异构化为亚稳态异构体的过程。一项挑战是要获得在足够长的波长下吸收以匹配太阳光谱的低分子量分子。在这里，我们表明，这可以通过两种降冰片（NBD）光电继电器连接到中央杂环，噻吩或咔唑来实现，通过炔烃附件。在这种方法中，相同的杂芳基用于同时调节两个光开关的特性，从而使分子量保持尽可能低。通过Sonogashira偶联反应制备了一系列NBD二聚体，这些化合物显示出显着的红移吸收，起始吸收高达468 nm，热半衰期为44秒至16小时。
• Aromatic enediyne derivatives, organic semiconductor thin films using the same and manufacturing methods thereof, and electronic devices incorporating such films
  申请人：Jeong Jeong Eun

  公开号：US20070120120A1

  公开（公告）日：2007-05-31

  Disclosed are aromatic enediyne derivatives, methods of manufacturing organic semiconductor thin films from such aromatic enediyne derivatives, and methods of fabricating electronic devices incorporating such organic semiconductor thin films. Aromatic enediyne derivatives according to example embodiments provide improved chemical and/or electrical stability which may improve the reliability of the resulting semiconductor devices. Aromatic enediyne derivatives according to example embodiments may also be suitable for deposition on various substrates via solution-based processes, for example, spin coating, at temperatures at or near room temperature to form a coating film that is then heated to form an organic semiconductor thin film. The availability of this reduced temperature processing allows the use of the aromatic enediynes derivatives on large substrate surfaces and/or on substrates not suitable for higher temperature processing. Accordingly, the organic semiconductor thin films according to example embodiments may be incorporated in thin film transistors, electroluminescent devices, solar cells, and memory devices.

  本发明涉及芳基炔衍生物，制造有机半导体薄膜的方法以及制造包括这种有机半导体薄膜的电子器件的方法。根据实施例，芳基炔衍生物提供了改善的化学和/或电学稳定性，这可以提高所得到的半导体器件的可靠性。根据实施例，芳基炔衍生物也可以通过基于溶液的工艺（例如旋涂）在室温或接近室温下沉积在各种基板上，形成一层涂层膜，然后加热形成有机半导体薄膜。这种低温处理的可用性允许在大型基板表面和/或不适合高温处理的基板上使用芳基炔衍生物。因此，根据实施例，有机半导体薄膜可以用于薄膜晶体管、电致发光器件、太阳能电池和存储器件。
• Organic semiconductor thin films using aromatic enediyne derivatives and manufacturing methods thereof, and electronic devices incorporating such films
  申请人：Jeong Eun Jeong

  公开号：US20090263932A1

  公开（公告）日：2009-10-22

  Disclosed are organic semiconductor thin films using aromatic enediyne derivatives, manufacturing methods thereof, and methods of fabricating electronic devices incorporating such organic semiconductor thin films. Aromatic enediyne derivatives according to example embodiments provide improved chemical and/or electrical stability which may improve the reliability of the resulting semiconductor devices. Aromatic enediyne derivatives according to example embodiments may also be suitable for deposition on various substrates via solution-based processes, for example, spin coating, at temperatures at or near room temperature to form a coating film that is then heated to form an organic semiconductor thin film. The availability of this reduced temperature processing allows the use of the aromatic enediynes derivatives on large substrate surfaces and/or on substrates not suitable for higher temperature processing. Accordingly, the organic semiconductor thin films according to example embodiments may be incorporated in thin film transistors, electroluminescent devices, solar cells, and memory devices.

  本文公开了使用芳香炔二烯衍生物的有机半导体薄膜，其制造方法以及制造包含此类有机半导体薄膜的电子器件的方法。根据实施例，芳香炔二烯衍生物提供了改进的化学和/或电气稳定性，这可能提高了所得到的半导体器件的可靠性。根据实施例，芳香炔二烯衍生物也可能适用于通过溶液基工艺，例如旋涂，在接近室温的温度下沉积在各种基底上，形成一层涂层膜，然后加热以形成有机半导体薄膜。这种降低温度处理的可用性允许在大的基底表面和/或不适合高温处理的基底上使用芳香炔二烯衍生物。因此，根据实施例，有机半导体薄膜可以应用于薄膜晶体管、电致发光器件、太阳能电池和存储器件中。
• Acid-Catalyzed [4+1]-Dearomatization Spiroannulation of Hydroquinones and Naphthols
  作者：Zhi Li、Nan Ding

  DOI：10.1055/a-2123-7565

  日期：2023.12

  convenient methods to access spirocyclic cyclohexadienone derivatives. The Lewis acid Bi(OTf)3 exhibited the best catalytic performance when a 1,2-dialkynylbenzene was used as the electrophile for the spiroannulation, whereas the Brønsted acid benzene-1,2-disulfonic acid was the best catalyst when 2-ethynylbenzylic esters were used as electrophiles. Most of the reaction conditions are mild, efficient, and

  富电子氢醌和萘酚衍生物的酸催化[4+1]-脱芳构化螺环化反应被证明是获得螺环环己二烯酮衍生物的便捷方法。当使用1,2-二炔基苯作为螺环化反应的亲电子试剂时，路易斯酸Bi(OTf) 3表现出最好的催化性能，而当使用2-乙炔基苯甲酯时，布朗斯台德酸苯-1,2-二磺酸是最好的催化剂被用作亲电子试剂。大多数反应条件温和、高效、操作简单。