5-ethynyl-5'-hexyl-2,2'-bithiophene | 1067426-48-5

• 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-ethynyl-5'-hexyl-2,2'-bithiophene
• 英文别名: 5-Ethynyl-5'-hexyl-2,2'-bithiophene；2-ethynyl-5-(5-hexylthiophen-2-yl)thiophene
• CAS: 1067426-48-5
• 化学式: C₁₆H₁₈S₂
• 分子量: 274.451
• InChiKey: ALMACYNHZGMVNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  5-ethynyl-5'-hexyl-2,2'-bithiophene 、 1-bromo-2,3,5,6-tetrafluoro-4-iodobenzene 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 以0.16 g的产率得到5-(1-ethynyl-4-bromo-tetrafluorophenyl)-5'-hexyl-2,2'-bithiophene
  参考文献：
  名称：

  Synthesis and Characterization of Fluorinated Heterofluorene-Containing Donor−Acceptor Systems

  摘要：

  A series of oligothiopheiie-perfluoro-9-heterofluorene donor-acceptor (DA) compounds was synthesized via a combination of nucleophilic aromatic substitution (SNArF) and palladium coupling reactions. These compounds are of interest as possible building blocks for materials with useful electron transport properties, since they possess relatively low LUMO energy levels of -3.3 to -3.6 eV (as determined by differential Pulse voltammetry), The HOMO-LUMO energy gaps, as determined by UV-vis spectroscopy, range between 2.4 and 2.5 eV, and photoluminescence emission spectra reveal lambda(ems) values in the range of 480-600 nm (corresponding to yellow-orange emission). Dilute solution-state photolummescence quantum yields were significantly lower than those of the pure acceptor heterofluorenes (0.02-0.38 for the DA compounds vs similar to 1 for the pure acceptors), and notable solvatochromisin in the fluorescence suggests emission from a charge-separated state. Theoretical calculations show that HOMO-level electron density is more localized on the thiophene fragment, while the LUMO level electron density is mostly associated with the electron-deficient portion of the molecule. Photovoltaic (PV) devices based on DA/poly-3-hexylthiophene (P3HT) blends exhibit improved performance over P3HT-only devices, suggesting the ability of these DA compounds to transport electrons in the solid state.

  DOI：

  10.1021/jo902488w
• 作为产物：
  描述：

  5-己基-2,2-二噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 三乙胺 、 potassium hydroxide 作用下， 以 氯仿 、 溶剂黄146 、 异丙醇 为溶剂， 反应 26.5h， 生成 5-ethynyl-5'-hexyl-2,2'-bithiophene
  参考文献：
  名称：

  Small asymmetric anthracene–thiophene compounds as organic thin-film transistors

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.07.041

文献信息

• 9,10-Disubstituted Octafluoroanthracene Derivatives via Palladium-Catalyzed Cross-Coupling
  作者：John F. Tannaci、Masahiro Noji、Jennifer L. McBee、T. Don Tilley

  DOI：10.1021/jo8017268

  日期：2008.10.17

  9,10-Dichlorooctafluoroanthracene (1) reacts with aryl boronic acids and terminal alkynes under palladium-catalyzed cross-coupling conditions to afford 9,10-diaryloctafluoroanthracenes (2a-e) and 9,10-dialkynyloctafluoroanthracenes (6a,b), respectively. Optical spectroscopy and cyclic voltammetry indicate that octafluoro-9,10-di(thiophen-2-yl)anthracene (2d) exhibits donor-acceptor character and a

  9,10-二氯八氟蒽（1）在钯催化的交叉偶联条件下与芳基硼酸和末端炔烃反应，分别制得9,10-二氟六氟蒽（2a-e）和9,10-二炔五氟蒽（6a，b）。光谱和循环伏安法表明，八氟-9,10-二（噻吩-2-基）蒽（2d）表现出给体-受体特性，相对于真空的LUMO能级为-3.27 eV。通过用NBS溴化2d，可以高收率获得官能化的5-溴噻吩-2-基衍生物（2e）。八氟-9,10-双[（（三甲基甲硅烷基）乙炔基]蒽（6a）的X射线晶体分析表明，固态结构模仿了柱状液晶的堆积，八氟蒽芯之间的π堆积距离为3.39 A 。此外，八氟-9
• J-aggregation induced low bandgap anthracene-based conjugated molecule for solution-processed solar cells
  作者：Jicheol Shin、Nam Su Kang、Kyung Hwan Kim、Tae Wan Lee、Jung-Il Jin、Minsik Kim、Kwangyeol Lee、Byeong Kwon Ju、Jae-Min Hong、Dong Hoon Choi

  DOI：10.1039/c2cc34109c

  日期：——

  A new anthracene-based X-shaped conjugated molecule, HBTATHT, was synthesized. Thin film transistors based on unannealed HBTATHT showed a carrier mobility of 0.15 cm2 V−1 s−1 (Ion/off = 7.9 × 106). Further, a solution processed solar cell made of HBTATHT exhibited promising power conversion efficiencies of 4.84% and 4.70% with PC61BM (1 : 0.8 wt ratio) and PC71BM (1 : 0.6 wt ratio), respectively.

  合成了一种新的基于蒽的X形共轭分子HBTATHT。基于未退火HBTATHT的薄膜晶体管显示出载流子迁移率为0.15 cm² V⁻¹ s⁻¹（Ion/off = 7.9 × 10⁶）。此外，由HBTATHT制成的溶液处理的太阳能电池分别与PC61BM（1 : 0.8 wt比）和PC71BM（1 : 0.6 wt比）显示出有前景的光电转换效率，分别为4.84%和4.70%。
• DIACETYLENE DERIVATIVE AND LIQUID CRYSTALLINE POLYMER HAVING DIACETYLENE STRUCTURE
  申请人：Arajawa Yuki

  公开号：US20130324684A1

  公开（公告）日：2013-12-05

  The present invention provides a diacetylene derivative represented by the following formula (A) which exhibits liquid crystallinity by itself and has a large refractive index anisotropy or does not exhibit liquid crystallinity by itself but exhibits a large refractive index anisotropy when added to a liquid crystalline compound: R1-Sp1-(Ar1) p -(Ar3) q -(Phe) r -C≡C—C≡C-(Phe) r -(Ar4) q -(Ar2) p -Sp2-R2  (A) (wherein R1 and R2 are a hydrogen, halogen, cyano, isothiocyanate, alkyl, alkenyl, alkynyl or reactive group, SP1 and SP2 are each a spacer group, Ar1 and Ar2 are each a non-substituted or substituted aromatic carbocyclic or heterocyclic group, Ar3 and Ar4 are each a non-substituted or substituted heterocyclic group, Phe is a non-substituted or substituted 1,4-phenylene group, and p, q and r are each 0 or 1.

  本发明提供了一种二乙炔衍生物，其由以下式(A)所表示，它本身表现出液晶性并具有大的折射率各向异性，或者虽然本身不具有液晶性，但当添加到液晶化合物中时表现出大的折射率各向异性：R1-Sp1-(Ar1)p-(Ar3)q-(Phe)r-C≡C—C≡C-(Phe)r-(Ar4)q-(Ar2)p-Sp2-R2  (A)（其中，R1和R2分别是氢、卤素、氰、异硫氰酸酯、烷基、烯基、炔基或反应基，SP1和SP2分别是间隔基，Ar1和Ar2分别是非取代或取代的芳香环烷基或杂环烷基，Ar3和Ar4分别是非取代或取代的杂环基，Phe是非取代或取代的1,4-苯基基团，p、q和r分别为0或1。）
• Diacetylene derivative and liquid crystalline polymer having diacetylene structure
  申请人：Arakawa Yuki

  公开号：US09139774B2

  公开（公告）日：2015-09-22

  The present invention provides a diacetylene derivative represented by the following formula (A) which exhibits liquid crystallinity by itself and has a large refractive index anisotropy or does not exhibit liquid crystallinity by itself but exhibits a large refractive index anisotropy when added to a liquid crystalline compound: R1-Sp1-(Ar1)p-(Ar3)q-(Phe)r-C≡C—C≡C-(Phe)r-(Ar4)q-(Ar2)p-Sp2-R2  (A) (wherein R1 and R2 are a hydrogen, halogen, cyano, isothiocyanate, alkyl, alkenyl, alkynyl or reactive group, SP1 and SP2 are each a spacer group, Ar1 and Ar2 are each a non-substituted or substituted aromatic carbocyclic or heterocyclic group, Ar3 and Ar4 are each a non-substituted or substituted heterocyclic group, Phe is a non-substituted or substituted 1,4-phenylene group, and p, q and r are each 0 or 1.

  本发明提供了一种二炔基衍生物，其由以下式（A）表示，它本身表现出液晶性并具有大的折射率各向异性，或者它本身不表现液晶性，但在加入液晶化合物时表现出大的折射率各向异性： R1-Sp1-(Ar1)p-(Ar3)q-(Phe)r-C≡C—C≡C-(Phe)r-(Ar4)q-(Ar2)p-Sp2-R2  (A) 其中，R1和R2分别为氢、卤素、氰、异硫氰酸酯、烷基、烯基、炔基或反应性基团，SP1和SP2分别为间隔基团，Ar1和Ar2分别为非取代或取代的芳香环烃或杂环烃基团，Ar3和Ar4分别为非取代或取代的杂环烃基团，Phe为非取代或取代的1,4-苯基基团，p、q和r分别为0或1。
• US9139774B2
  申请人：——

  公开号：US9139774B2

  公开（公告）日：2015-09-22