2-dodecyl-5-ethynylthiophene | 355838-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-dodecyl-5-ethynylthiophene
• CAS: 355838-03-8
• 化学式: C₁₈H₂₈S
• 分子量: 276.486
• InChiKey: FKQIGXGDMMSNLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  19.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-dodecyl-5-ethynylthiophene 在 甲醇 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.75h， 生成 1-(5-dodecylthiophen-2-yl)penta-1,4-diyn-3-ol
  参考文献：
  名称：

  Phenyl dialkynylcarbinols, a Bioinspired Series of Synthetic Antitumor Acetylenic Lipids

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c00859
• 作为产物：
  描述：

  4-(5-dodecylthiophen-2-yl)-2-methylbut-3-yn-2-ol 在 potassium hydroxide 作用下， 以 甲苯 为溶剂， 生成 2-dodecyl-5-ethynylthiophene
  参考文献：
  名称：

  用于有机太阳能电池应用的新型 2,6-连接蒽-苯并噻二唑基聚合物系列的合成和表征

  摘要：

  通过直接芳基化聚合反应制备了一系列基于 2,6-连接蒽的中带隙交替供体-受体共轭聚合物，两侧为噻吩基供体单元和苯并噻二唑受体单元 (BT)。制备的聚合物在溶液和薄膜中均显示出多个吸收带，光学带隙在 1.75–1.85 eV 范围内。与具有炔基取代基的聚合物相比，在蒽重复单元的 9,10-位上具有烷基噻吩基乙炔基取代基的聚合物显示出更宽的吸收光谱。聚[9,10-双[2-乙炔基-5-十二烷基噻吩]-蒽-2,6-二基-alt的光伏研究-4,7-二（噻吩-2-基）苯并 [c]（Gopalakrishnan 等人，2022 年；Gokulnath 等人，2021 年；Bian 等人，2012 年）[1,2,5]噻二唑] PATA( D)该系列中的TBT，与苯基-C70-丁酸甲酯PC71BM共混，功率转换效率PCE为0.76%，开路电压Voc为0.54 V。

  DOI：

  10.1016/j.tet.2023.133416

文献信息

• Highly Coplanar Polythiophenes with –C≡CR Side Chains: Self-Assembly, Linear and Nonlinear Optical Properties, and Piezochromism
  作者：Takakazu Yamamoto、Takao Sato、Takayuki Iijima、Masahiro Abe、Hiroki Fukumoto、Take-aki Koizumi、Motoaki Usui、Yoshiyuki Nakamura、Takehiko Yagi、Hiroyuki Tajima、Taku Okada、Shintaro Sasaki、Hideo Kishida、Arao Nakamura、Takashi Fukuda、Akira Emoto、Hirobumi Ushijima、Chisato Kurosaki、Hiroshi Hirota

  DOI：10.1246/bcsj.82.896

  日期：2009.7.15

  Self-assembly of polythiophenes with –C≡CR (R = alkyl, phenyl, etc.) side chains has been investigated. Seven new polymers consisting of head-to-head and tail-to-tail 2,2′-bithiophenes with –C≡CR side chains were synthesized. The new polymers include alternating copolymers between bithiophenes with –C≡C–alkyl side chains and thiophene and those between bithiophenes with –C≡C–alkyl side chains and 2,2′-bithiophene. The polythiophene main chain is considered to be coplanar because of the absence of steric repulsion between the main chain and the –C≡CR side chain. Single-crystal X-ray crystallography and DFT calculations indicated that the head-to-head- and tail-to-tail-2,2′-bithiophenes with –C≡CR side chains were coplanar. The polythiophenes with –C≡CR side chains showed a strong tendency to self-assemble, and assumed edge-on alignment and side-on alignment on the surface of substrates. Self-assembly caused a decrease in the π–π* transition energy of the polymers by 0.3–0.4 eV. A copolymer of thiophene and dialkoxy-p-phenylene showed analogous self-assembly. The polythiophenes with –C≡CR side chains showed piezochromism, with a decrease in the π–π* transition energy by about 0.2 eV at 10 GPa. Head-to-head-P3(C≡C–Dec)Th with a –C≡C–decyl side chain gave a larger optical third-order nonlinear susceptibility χ(3) than regio-regular poly(3-hexylthiophene)s.

  已研究了具有–C≡CR（R = 烷基，苯基等）侧链的聚噻吩的自组装。合成了由具有–C≡CR侧链的头对头和尾对尾2,2′-联噻吩组成的七种新型聚合物。这些新聚合物包括具有–C≡C–烷基侧链的联噻吩与噻吩之间的交替共聚物，以及具有–C≡C–烷基侧链的联噻吩与2,2′-联噻吩之间的交替共聚物。由于主链与–C≡CR侧链之间不存在空间排斥，因此聚噻吩主链被认为是共平面的。单晶X射线晶体学和DFT计算表明，具有–C≡CR侧链的头对头和尾对尾2,2′-联噻吩是共平面的。具有–C≡CR侧链的聚噻吩显示出强烈的自组装倾向，并在基底表面呈现出边缘对齐和侧面对齐。自组装导致聚合物的π–π*跃迁能量降低了0.3–0.4 eV。噻吩与二烷氧基-对苯二烯的共聚物显示了类似的自组装行为。具有–C≡CR侧链的聚噻吩显示出压致变色现象，在10 GPa下π–π*跃迁能量降低了约0.2 eV。具有–C≡C-癸基侧链的头对头-P3(C≡C-癸基)噻吩的光学三阶非线性极化率χ(3)大于区域规整聚(3-己基噻吩)。
• Star­like substituted hexaarylbenzenes: synthesis and mesomorphic properties
  作者：Yanhou Geng、Andreas Fechtenkötter、Klaus Müllen

  DOI：10.1039/b101163o

  日期：——

  A series of hexaarylbenzenes (1–6) with a variety of different aryl arms (i.e. phenyl, biphenylyl, mono-, bi-, and terthienylyl) around a benzene core, decorated with flexible dodecyl chains on the terminal positions, were synthesized. Their mesomorphic behaviors were studied by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (XD) techniques. Compounds 1–3, which have a hexaphenylbenzene core, form columnar mesophases. In particular 3, in which the core is composed of hexaphenylbenzene surrounded by thiophene rings, shows a stable columnar mesophase (d-Dh) over a large temperature range compared to its phenyl analogs, hexakis(4-dodecylphenyl-4-yl)benzene (1) and hexakis(4′-dodecylbiphenylyl)benzene (2). Compounds 4–6, hexa(oligo-α-thienylyl)benzenes, tend to form less ordered mesophases after annealing for a longer time. Compounds 4 and 5 form discotic nematic mesophases (Nd) at temperatures well below the decomposition temperature.

  合成了一系列六芳基苯 (1-6)，在苯核周围具有各种不同的芳基臂（即苯基、联苯基、单、双和三噻吩基），并在末端位置用柔性十二烷基链装饰。通过差示扫描量热法 (DSC)、偏光光学显微镜 (POM) 和 X 射线衍射 (XD) 技术研究了它们的介晶行为。化合物 1-3 具有六苯基苯核心，形成柱状中间相。特别是3，其核心由被噻吩环包围的六苯基苯组成，与其苯基类似物六(4-十二烷基苯基-4-基)苯相比，在很大的温度范围内表现出稳定的柱状中间相(d-Dh)。 1) 和六(4'-十二烷基联苯基)苯(2)。化合物 4-6，六（低聚-α-噻吩基）苯，在长时间退火后往往会形成有序性较低的中间相。化合物 4 和 5 在远低于分解温度的温度下形成盘状向列中间相 (Nd)。
• Single Microwire Transistors of Oligoarenes by Direct Solution Process
  作者：Yan Zhou、Wen-Jun Liu、Yuguo Ma、Hailiang Wang、Limin Qi、Yong Cao、Jian Wang、Jian Pei

  DOI：10.1021/ja075045f

  日期：2007.10.1

  A condensed benzothiophene peripherally carrying rich sulfur atoms favoring π−π stacking is developed through facile approaches. The 1H NMR and the absorption spectra strongly indicate that this molecule easily forms the self-assembled structures in solutions. Microwires directly precipitate from solution, and such 1D self-assembled nano- and microstructures can be controlled and tuned by changing

  通过简便的方法开发了外围携带有利于 π-π 堆积的富硫原子的稠合苯并噻吩。1H NMR 和吸收光谱强烈表明该分子很容易在溶液中形成自组装结构。微线直接从溶液中沉淀出来，这种一维自组装纳米和微结构可以通过改变溶剂和浇铸在各种基材上来控制和调整。基于这种稠合苯并噻吩的单微线晶体管很容易通过溶液工艺制造，载流子迁移率高达 0.01 cm2 V-1 s-1。
• Small asymmetric anthracene–thiophene compounds as organic thin-film transistors
  作者：Baji Shaik、Ji Hee Park、Tae Kyu An、Young Ri Noh、Soon Byung Yoon、Chan Eon Park、Young Jin Yoon、Yun-Hi Kim、Sang-Gyeong Lee

  DOI：10.1016/j.tet.2013.07.041

  日期：2013.9

  Anthracene and thiophene compounds are promising materials for OTFTs. We report here, the synthesis, as well as the physical, thermal, and optoelectronic properties of alkyl-substituted asymmetric anthracene-thiophene compounds connected by a bridged triple bond. The target molecules were synthesized using 2-bromoanthracene as the starting material, and the proceeding reactions included alkylation, bromination, and the Sonogashira coupling reaction. The synthesized compounds were both thermally and electrochemically stable. Among the synthesized compounds, HTEA (7a) and DTEA (7b) showed mobility and on/off ratio values of 1.3x10(-1) cm(2)/V s, 2.6 x 10(6) and 2.0x10(-2) cm(2)/V s, 1.0x10(6), respectively. (C) 2013 Elsevier Ltd. All rights reserved.