2,5-bis(para-N,N-dimethylaminophenylethynyl)thiophene | 778593-54-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-bis(para-N,N-dimethylaminophenylethynyl)thiophene
• 英文别名: 2,5-[di(p-N,N-dimethylamino)phenylethynyl]thiophene；2,5-bis(4-N,N-dimethylaminophenylethynyl)-thiophene；2,5-di(p-N,N-dimethylaminophenylethynyl)thiophene；4-[2-[5-[2-[4-(dimethylamino)phenyl]ethynyl]thiophen-2-yl]ethynyl]-N,N-dimethylaniline
• CAS: 778593-54-7
• 化学式: C₂₄H₂₂N₂S
• 分子量: 370.518
• InChiKey: PXIHQSHAFAVWHM-UHFFFAOYSA-N

物化性质

• 熔点：
  181-183 °C
• 沸点：
  565.3±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(OC)₅Mo=BN(SiMe₃)₂] 、 2,5-bis(para-N,N-dimethylaminophenylethynyl)thiophene 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 2,5-bis-{μ-BN(SiMe3)2((C6H4-4-NMe2)C=C)}thiophene
  参考文献：
  名称：

  Borylene-Based Direct Functionalization of Organic Substrates: Synthesis, Characterization, and Photophysical Properties of Novel π-Conjugated Borirenes

  摘要：

  Room temperature photolysis of aminoborylene complexes, [(CO)(5)M=B=N(SiMe3)(2)] (1: M = Cr, 2: Mo) in the presence of a series of alkynes and diynes, 1,2-bis(4-methoxyphenyl)ethyne, 1,2-bis(4(trifluoromethyl)phenyl)ethyne, 1,4-diphenylbuta-1,3-diyne, 1,4-bis(4-methoxyphenyl)buta-1,3-diyne, 1,4-bis(trimethylsilylethynyl) benzene and 2,5-bis(4-N,N-dimethylaminophenylethynyl)thiophene led to the isolation of novel mono and bis-bis-(trimethylsilyl)aminoborirenes in high yields, that is [(RC=CR)(mu-BN(SiMe3)2], (3: R = C6H4-4-OMe and 4: R = C6H4-4-CFA [{(mu-BN(SiMe3)(2)(RC=C-)}(2)], (5: R = C6H5 and 6: R = C6H4-4-OMe); [1,4-bis-{(mu-BN(SiMe3)(2)(SiMe3C=C)}benzene], 7 and [2,5-bis-{(mu-BN(SiMe3)(2) ((C6H4NMe2)-C=C)}-thiophene], 8. All borirenes were isolated as light yellow, air and moisture sensitive solids. The new borirenes have been characterized in solution by H-1, B-11, C-13 NMR spectroscopy and elemental analysis and the structural types were unequivocally established by crystallographic analysis of compounds 6 and 7. DFT calculations were performed to evaluate the extent of pi-conjugation between the electrons of the carbon backbone and the empty p, orbital of the boron atom, and TD-DFT calculations were carried out to examine the nature of the electronic transitions.

  DOI：

  10.1021/ja902198z
• 作为产物：
  描述：

  4-(3-methyl-3-hydroxy-1-butynyl)-N,N-dimethylaniline 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper(l) iodide 作用下， 以 三乙胺 、 甲苯 为溶剂， 生成 2,5-bis(para-N,N-dimethylaminophenylethynyl)thiophene
  参考文献：
  名称：

  N，N-二甲基和噻吩基封端的2,5-（芳乙炔基）噻吩低聚物结构的合成及光学性质

  摘要：

  通过在末端乙炔之间进行杂偶合，合成对位封端的（N，N-二甲基氨基苯基）和2'-噻吩基乙炔基2,5-噻吩低聚物结构：p-（N，N-二甲基氨基苯基）乙炔（3）[或1- （p-（N，N-二甲基氨基苯基）-2- p-（乙炔基苯基）乙炔，4]；p-（β-乙烯基-2'-噻吩基）苯基乙炔（E -9）[或p-（β-乙炔基- Cl 2 Pd（PPh 3）2催化的2'-噻吩基）苯基乙炔11]和2,5-二碘噻吩/ CuI系统，良率至良率。通过3，，5'-二[（三甲基甲硅烷基乙炔基）苯基] x -1-之间的杂合制备2,5-二[（3'，5'-二（三甲基甲硅烷基乙炔基）苯基] x -1-乙炔基]噻吩低聚物乙炔（n  = 0–2）末端乙炔和2,5-二碘噻吩，收率很好。通过特定的保护-脱保护方法有效地制备了末端乙炔。所有获得的乙炔基苯基化合物均显示出荧光辐射发射，红移为随着链共轭增加的波长。

  DOI：

  10.1016/j.tetlet.2004.07.123

文献信息

• Synthesis, photophysics and molecular structures of luminescent 2,5-bis(phenylethynyl)thiophenes (BPETs)
  作者：Jamie S. Siddle、Richard M. Ward、Jonathan C. Collings、Simon R. Rutter、Laurent Porrès、Lucas Applegarth、Andrew Beeby、Andrei S. Batsanov、Amber L. Thompson、Judith A. K. Howard、Abdou Boucekkine、Karine Costuas、Jean-François Halet、Todd B. Marder

  DOI：10.1039/b701172e

  日期：——

  The spectroscopic studies of 1a–h and 2 show that both electron donating and electron withdrawing para-subsituents on the phenyl rings shift the absorption and emission maxima to lower energies, but that acceptors are more efficient in this regard. The short singlet lifetimes and modest fluorescence quantum yields (ca. 0.2–0.3) observed are characteristic of rapid intersystem crossing. The single-crystal

  两个当量对位乙炔基苯的Sonogashira交叉偶联与2,5-二碘噻吩为制备2，5-双（对-R-苯基乙炔基）噻吩（R = H，Me，OMe，CF 3，NMe 2，NO 2，CN和CO 2 Me）提供了简单的合成途径（1a – h）。同样地，2,5-双（五氟苯基乙炔基）噻吩（2）是通过耦合制备的。2,5-二碘噻吩 和 五氟苯基乙炔。所有化合物均通过NMR，IR，拉曼光谱和质谱，元素分析进行​​表征，并测量了它们的吸收和发射光谱，量子产率和寿命。1a - h和2的光谱研究表明，苯环上的给电子和吸电子对位取代基都将吸收和发射最大值转移到较低的能量，但是受体在这方面更有效。观察到的短单峰寿命和适度的荧光量子产率（约0.2-0.3）是系统间快速杂交的特征。2,5-双（苯基乙炔基）噻吩，2,5-双（对位）的单晶结构-碳甲氧基苯基乙炔基）噻吩，2,5-双（对甲基苯基乙炔基）噻吩和2,5-双（五氟苯基乙炔基）噻吩通过X射线衍射在120
• テトラシアノブタジエン誘導体
  申请人：財団法人理工学振興会

  公开号：JP2005200336A

  公开（公告）日：2005-07-28

  PROBLEM TO BE SOLVED: To obtain an organic compound that is useful as an electronic material and exhibits both oxidation and reduction properties.

  SOLUTION: The tetracyanobutadiene derivative is represented by general formula (1). Since the tetracyanobutadiene derivative contains an electron donative group in a tetracyanobutadiene derivative having high electron affinity, the tetracyanobutadiene derivative has electron-donating property besides electron-accepting property and both oxidation and reduction properties.

  COPYRIGHT: (C)2005,JPO&NCIPI

  需要解决的问题：获得一种有用于电子材料的有机化合物，同时表现出氧化和还原性质。 解决方案：四氰基丁二烯衍生物由通式（1）表示。由于四氰基丁二烯衍生物中含有一个电子给予基团，具有高电子亲和力的四氰基丁二烯衍生物除了具有电子受体性质外，还具有电子给予性质和氧化还原性质。 版权所有：（C）2005，JPO＆NCIPI
• Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: fluorescence properties
  作者：J. Gonzalo Rodriguez、Jorge Esquivias、Antonio Lafuente、Laura Rubio

  DOI：10.1016/j.tet.2006.01.032

  日期：2006.3

  Nano conjugated thienylethenyl and thienylethynyl Compounds with controlled Structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynylphenyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(iodo)thiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and optical properties of conjugated N,N-dimethyl and thienyl end-capped 2,5-(arylethynyl)thiophene oligomer structures
  作者：J. Gonzalo Rodrı́guez、Antonio Lafuente、Laura Rubio、Jorge Esquivias

  DOI：10.1016/j.tetlet.2004.07.123

  日期：2004.9

  by the Cl2Pd(PPh3)2/CuI system, in good to excellent yields. The 2,5-di[(3′,5′-di(trimethylsilylethynyl)phenyl]x-1-ethynyl]thiophene oligomers were prepared by heterocoupling between 3′,5′-di[(trimethylsilylethynyl)phenyl]x-1-ethyne (n = 0–2) terminal acetylenes and 2,5-diiodothiophene, in excellent yields. The terminal acetylenes were efficiently prepared by a specific protection-deprotection methodology

  通过在末端乙炔之间进行杂偶合，合成对位封端的（N，N-二甲基氨基苯基）和2'-噻吩基乙炔基2,5-噻吩低聚物结构：p-（N，N-二甲基氨基苯基）乙炔（3）[或1- （p-（N，N-二甲基氨基苯基）-2- p-（乙炔基苯基）乙炔，4]；p-（β-乙烯基-2'-噻吩基）苯基乙炔（E -9）[或p-（β-乙炔基- Cl 2 Pd（PPh 3）2催化的2'-噻吩基）苯基乙炔11]和2,5-二碘噻吩/ CuI系统，良率至良率。通过3，，5'-二[（三甲基甲硅烷基乙炔基）苯基] x -1-之间的杂合制备2,5-二[（3'，5'-二（三甲基甲硅烷基乙炔基）苯基] x -1-乙炔基]噻吩低聚物乙炔（n  = 0–2）末端乙炔和2,5-二碘噻吩，收率很好。通过特定的保护-脱保护方法有效地制备了末端乙炔。所有获得的乙炔基苯基化合物均显示出荧光辐射发射，红移为随着链共轭增加的波长。
• Borylene-Based Direct Functionalization of Organic Substrates: Synthesis, Characterization, and Photophysical Properties of Novel π-Conjugated Borirenes
  作者：Holger Braunschweig、Thomas Herbst、Daniela Rais、Sundargopal Ghosh、Thomas Kupfer、Krzysztof Radacki、Andrew G. Crawford、Richard M. Ward、Todd B. Marder、Israel Fernández、Gernot Frenking

  DOI：10.1021/ja902198z

  日期：2009.7.1

  Room temperature photolysis of aminoborylene complexes, [(CO)(5)M=B=N(SiMe3)(2)] (1: M = Cr, 2: Mo) in the presence of a series of alkynes and diynes, 1,2-bis(4-methoxyphenyl)ethyne, 1,2-bis(4(trifluoromethyl)phenyl)ethyne, 1,4-diphenylbuta-1,3-diyne, 1,4-bis(4-methoxyphenyl)buta-1,3-diyne, 1,4-bis(trimethylsilylethynyl) benzene and 2,5-bis(4-N,N-dimethylaminophenylethynyl)thiophene led to the isolation of novel mono and bis-bis-(trimethylsilyl)aminoborirenes in high yields, that is [(RC=CR)(mu-BN(SiMe3)2], (3: R = C6H4-4-OMe and 4: R = C6H4-4-CFA [(mu-BN(SiMe3)(2)(RC=C-)}(2)], (5: R = C6H5 and 6: R = C6H4-4-OMe); [1,4-bis-(mu-BN(SiMe3)(2)(SiMe3C=C)}benzene], 7 and [2,5-bis-(mu-BN(SiMe3)(2) ((C6H4NMe2)-C=C)}-thiophene], 8. All borirenes were isolated as light yellow, air and moisture sensitive solids. The new borirenes have been characterized in solution by H-1, B-11, C-13 NMR spectroscopy and elemental analysis and the structural types were unequivocally established by crystallographic analysis of compounds 6 and 7. DFT calculations were performed to evaluate the extent of pi-conjugation between the electrons of the carbon backbone and the empty p, orbital of the boron atom, and TD-DFT calculations were carried out to examine the nature of the electronic transitions.