2,5-diethynyl-3-butylthiophene | 116954-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-diethynyl-3-butylthiophene
• 英文别名: 3-Butyl-2,5-diethynylthiophene；3-butyl-2,5-diethynylthiophene
• CAS: 116954-14-4
• 化学式: C₁₂H₁₂S
• 分子量: 188.293
• InChiKey: BQFYUGBVVWKQGO-UHFFFAOYSA-N

物化性质

• 沸点：
  295.4±40.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  cis-Ru(dppe)₂Cl₂ 、 2,5-diethynyl-3-butylthiophene 在 sodium hexaflorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以77%的产率得到
  参考文献：
  名称：

  噻吩乙炔基间隔基3位上的取代基对二钌（II）有机金属丝状络合物的电子性质的作用。

  摘要：

  一系列有机金属配合物的[氯（DPPE）2的Ru-C≡C-（3-R-C 4 H ^ 2 S）-C≡C-茹（DPPE）2 CL]（3-R-C 4 H ^ 2小号= 3-取代的噻吩基部分; R = -H，-C 2 H ^ 5，-C 3 H ^ 7，-C 4 H ^ 9，-C 6 H ^ 13，-OMe，-CN在5 一- 5 克分别）已经通过在噻吩基乙炔基桥接单元上3位取代基的系统变化来合成。铜（II）线状络合物（5  a – 5  g）是通过噻吩乙炔基桥接单元HC≡C-（3-R-C 4 H 2 S）-C≡CH（4  a – 4  g）与顺式-[Ru（dppe）2 Cl 2]。线状二钌（II）络合物在0.0-0.8 V的电位范围内经历了两个连续的电化学氧化过程。有趣的是，两个氧化还原波之间的波分离在很大程度上受到噻吩基乙炔基3位上的取代基的影响。因此，噻吩基乙炔基桥接单元在3位上的取代对于调节电子

  DOI：

  10.1002/asia.202000755
• 作为产物：
  描述：

  3-丁基噻吩 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.08h， 生成 2,5-diethynyl-3-butylthiophene
  参考文献：
  名称：

  噻吩乙炔基间隔基3位上的取代基对二钌（II）有机金属丝状络合物的电子性质的作用。

  摘要：

  一系列有机金属配合物的[氯（DPPE）2的Ru-C≡C-（3-R-C 4 H ^ 2 S）-C≡C-茹（DPPE）2 CL]（3-R-C 4 H ^ 2小号= 3-取代的噻吩基部分; R = -H，-C 2 H ^ 5，-C 3 H ^ 7，-C 4 H ^ 9，-C 6 H ^ 13，-OMe，-CN在5 一- 5 克分别）已经通过在噻吩基乙炔基桥接单元上3位取代基的系统变化来合成。铜（II）线状络合物（5  a – 5  g）是通过噻吩乙炔基桥接单元HC≡C-（3-R-C 4 H 2 S）-C≡CH（4  a – 4  g）与顺式-[Ru（dppe）2 Cl 2]。线状二钌（II）络合物在0.0-0.8 V的电位范围内经历了两个连续的电化学氧化过程。有趣的是，两个氧化还原波之间的波分离在很大程度上受到噻吩基乙炔基3位上的取代基的影响。因此，噻吩基乙炔基桥接单元在3位上的取代对于调节电子

  DOI：

  10.1002/asia.202000755

文献信息

• Improvement of the Extended One-Pot (EOP) Procedure To Form Poly(aryleneethynylene)s and Investigation of Their Electrical and Optical Properties
  作者：R. Pizzoferrato、M. Berliocchi、A. Di Carlo、P. Lugli、M. Venanzi、A. Micozzi、A. Ricci、C. Lo Sterzo

  DOI：10.1021/ma0216829

  日期：2003.4.1

  A series of pi-conjugated homopolymers of type poly(aryleneethynylene) (PAE), [-Ar-Cequivalent toC-](n), (Ar = 2,5-bis(butoxy)benzene (7a), 2,5-bis(octyloxy)benzene (7b), 2,5-bis(hexadecyloxy)benzene (7c), 3-butylthiophene (7d), and 3-hexadecylthiophene (7e)) have been prepared by further improvement of the palladium-catalyzed Extended One-Pot (EOP) synthetic protocol. With the use of dioxane as solvent and higher reaction temperature (110 degreesC), much higher polymerization degree, improved catalytic efficiency, and increased material purity were obtained. Numerical simulations have been performed in a series of different conjugated polymers in order to evaluate the role of the connection between aromatic rings in the maintaining of an effective electronic conjugation through the polymer chain. Experimentally, the conjugation properties have been investigated by means of photophysical measurements in liquid solution and in solid-state films. The electric transport properties have been characterized in view of applications to electronic devices.
• A Joint Experimental and Computational Study on the Electronic Communication in Diethynylaryl‐Bridged (η ⁵ ‐C ₅ H ₅ )Fe(η ² ‐dppe) and (η ⁵ ‐C ₅ H ₅ )Fe(CO) ₂ Units
  作者：Laura Medei、Laura Orian、Oleg V. Semeikin、Mikhail G. Peterleitner、Nikolai A. Ustynyuk、Saverio Santi、Christian Durante、Antonella Ricci、Claudio Lo Sterzo

  DOI：10.1002/ejic.200600024

  日期：2006.7

  AbstractA family of bimetallic complexes [Cp(CO)2Fe–C≡C–Ar–C≡C–Fe(CO)2Cp] Cp = C5H5; 6a–g: Ar = C4H2S (a), 3‐(C4H9)‐C4HS (b), 3‐(C16H33)‐C4HS (c), C6H4 (d), 2,5‐bis(OC4H9)‐C6H2 (e), 2,5‐bis(OC8H17)‐C6H2 (f), (C6H4)2 (g)} was prepared by the three‐step Pd‐catalysed extended one‐pot (EOP) synthetic protocol from Bu3Sn–C≡CH, X–Ar–X (X = I, Br) and Cp(CO)2FeI. Complexes 6a,d,g were then exposed to ultraviolet irradiation in the presence of an equivalent amount of 1,2‐bis(diphenylphosphanyl)ethane (dppe) to form the corresponding bimetallic complexes [Cp(dppe)Fe–C≡C–Ar–C≡C–Fe(dppe)Cp] (7a,d,g). Compounds 6a–g and 7a,d,g were characterised by cyclic voltammetry (CV). The most significant electrochemical information comes from the oxidation of the dppe derivatives. The ΔE° separations between the subsequent reversible waves suggest that the efficiency of the metal–metal electronic coupling decreases in the order 7a > 7d > 7g. Complexes 7a and 7g were also chemically oxidised with [Fe(Cp*)]2[BF4] Cp* = C5(CH3)5} and [Fe(Cp)]2[BF4] respectively, and the near infrared (NIR) spectra of the mixed‐valence species 7a+ and 7g+ were recorded. A strong intervalence transition (IT) band was observed only for the radical cation 7a+. While this finding confirms the existence of an electronic interaction between the two termini when a 2,5‐thiophene group is present in the spacer, the NIR spectrum of 7g+ reveals a reduced efficiency in conveying electrons when the C4H2S moiety is replaced by a 4,4′‐biphenyl. In order to rationalise and quantify the extent of electronic communication, ruled by geometrical and electronic factors, density functional computational results on selected [Cp (PH3)2Fe] and [Cp(CO)2Fe] binuclear model complexes are reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Role of Substituents at 3‐position of Thienylethynyl Spacer on Electronic Properties in Diruthenium(II) Organometallic Wire‐like Complexes
  作者：Sourav Saha Roy、Sabyasachi Roy Chowdhury、Sabyashachi Mishra、Sanjib K. Patra

  DOI：10.1002/asia.202000755

  日期：2020.10.16

  (DFT) calculations of the selected diruthenium wire‐like complexes (5 a–5 e) with different alkyl appendages are performed. The theoretical data demonstrate that incorporation of alkyl groups to the thienylethynyl entity leaves unsymmetrical spin densities, thus affecting the electronic properties. The voltammetric features of the other two Ru(II) alkynyl complexes 5 f and 5 g (with −OMe and −CN group

  一系列有机金属配合物的[氯（DPPE）2的Ru-C≡C-（3-R-C 4 H ^ 2 S）-C≡C-茹（DPPE）2 CL]（3-R-C 4 H ^ 2小号= 3-取代的噻吩基部分; R = -H，-C 2 H ^ 5，-C 3 H ^ 7，-C 4 H ^ 9，-C 6 H ^ 13，-OMe，-CN在5 一- 5 克分别）已经通过在噻吩基乙炔基桥接单元上3位取代基的系统变化来合成。铜（II）线状络合物（5  a – 5  g）是通过噻吩乙炔基桥接单元HC≡C-（3-R-C 4 H 2 S）-C≡CH（4  a – 4  g）与顺式-[Ru（dppe）2 Cl 2]。线状二钌（II）络合物在0.0-0.8 V的电位范围内经历了两个连续的电化学氧化过程。有趣的是，两个氧化还原波之间的波分离在很大程度上受到噻吩基乙炔基3位上的取代基的影响。因此，噻吩基乙炔基桥接单元在3位上的取代对于调节电子