2,5-diiodo-3-hexadecylthiophene | 233667-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,5-diiodo-3-hexadecylthiophene
• 英文别名: 2,5-diodo-3-hexadecylthiophene；3-Hexadecyl-2,5-diiodothiophene
• CAS: 233667-56-6
• 化学式: C₂₀H₃₄I₂S
• 分子量: 560.365
• InChiKey: JJZSOEXCQXPZEM-UHFFFAOYSA-N

物化性质

• 沸点：
  495.4±45.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  三丁基乙烯锡 、 2,5-diiodo-3-hexadecylthiophene 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 生成 2,5-bis(ethynyl)-3-(hexadecyl)thiophene
  参考文献：
  名称：

  从芳族碘化物到炔基炔烃的便捷捷径，及其在直接制备聚乙炔和多金属乙炔聚合物中的用途

  摘要：

  芳族碘化物ArI和三丁基（乙炔基）锡卜的钯-催化的交叉偶联反应（Stille偶联）3 SnCCH形成芳族乙炔化ArCCH和副产物三丁基锡，碘化卜3在等摩尔量SNI 。在原位添加二异丙氨基锂（LDA）于该粗混合物直接得到的三丁基（乙炔基）锡芳烃ArCCSnBu 3以高收率。在双的情况下（iodoaromatic）IArI（AR =苯基，噻吩），这种直接变换，得到相应的二[三丁基（乙炔基）锡]衍生物卜3 SnCCArCC SnBu 3。在Pd的存在下，该后一种物质可以与第二个双（碘代芳族）或双（金属碘化物）单元直接反应，以形成乙炔和金属乙炔聚合物，其中定制的单体单元插入立体有规聚合物链中。

  DOI：

  10.1016/s0022-328x(98)01124-3
• 作为产物：
  描述：

  3-正十六基噻吩 在 碘 、 硝酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以81%的产率得到2,5-diiodo-3-hexadecylthiophene
  参考文献：
  名称：

  从芳族碘化物到炔基炔烃的便捷捷径，及其在直接制备聚乙炔和多金属乙炔聚合物中的用途

  摘要：

  芳族碘化物ArI和三丁基（乙炔基）锡卜的钯-催化的交叉偶联反应（Stille偶联）3 SnCCH形成芳族乙炔化ArCCH和副产物三丁基锡，碘化卜3在等摩尔量SNI 。在原位添加二异丙氨基锂（LDA）于该粗混合物直接得到的三丁基（乙炔基）锡芳烃ArCCSnBu 3以高收率。在双的情况下（iodoaromatic）IArI（AR =苯基，噻吩），这种直接变换，得到相应的二[三丁基（乙炔基）锡]衍生物卜3 SnCCArCC SnBu 3。在Pd的存在下，该后一种物质可以与第二个双（碘代芳族）或双（金属碘化物）单元直接反应，以形成乙炔和金属乙炔聚合物，其中定制的单体单元插入立体有规聚合物链中。

  DOI：

  10.1016/s0022-328x(98)01124-3

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)