1,4-bis(propyloxy)-2,5-diiodobenzene | 221292-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-bis(propyloxy)-2,5-diiodobenzene
• 英文别名: 1,4-di-iodo-2,5-di-n-propoxybenzene；1,4-diiodo-2,5-dipropoxybenzene；1,4-Diiod-2,5-dipropoxybenzol；Benzene, 1,4-diiodo-2,5-dipropoxy-
• CAS: 221292-48-4
• 化学式: C₁₂H₁₆I₂O₂
• 分子量: 446.067
• InChiKey: XEIABPQMDIQKBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis(propyloxy)-2,5-diiodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 哌啶 、 sodium hydroxide 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 42.91h， 生成 1-[4-(2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[4-(2,5-dipropoxy-4-ethynylphenylethynyl)phenylethynyl]-2,5-dipropoxybenzene
  参考文献：
  名称：

  单分散低聚（1,4-亚苯基乙炔）的制备及非线性光学

  摘要：

  具有增溶丙氧基侧链的低聚（1,4-亚苯基乙炔基）1a-e 是通过使用 Hagihara-Sonogashira 偶联反应制备的。合成策略基于构建块系统和可以选择性裂解的三甲基甲硅烷基和三异丙基甲硅烷基保护基团的使用。随着重复单元数量的增加，共轭的延伸引起长波长吸收的红移和第二超极化率|γ|的超线性增加。相应的三次谐波生成 (THG) 测量是使用聚苯乙烯矩阵和可变激光波长进行的。我们得出结论，共轭长度远大于 5 个重复单元。

  DOI：

  10.1002/1099-0690(200112)2001:23<4431::aid-ejoc4431>3.0.co;2-j
• 作为产物：
  描述：

  1,4-二正丙氧基苯 在 potassium iodate 、 硫酸 、 碘 作用下， 以 四氯化碳 、 水 、 溶剂黄146 为溶剂， 反应 24.0h， 以82%的产率得到1,4-bis(propyloxy)-2,5-diiodobenzene
  参考文献：
  名称：

  单分散低聚（1,4-亚苯基乙炔）的制备及非线性光学

  摘要：

  具有增溶丙氧基侧链的低聚（1,4-亚苯基乙炔基）1a-e 是通过使用 Hagihara-Sonogashira 偶联反应制备的。合成策略基于构建块系统和可以选择性裂解的三甲基甲硅烷基和三异丙基甲硅烷基保护基团的使用。随着重复单元数量的增加，共轭的延伸引起长波长吸收的红移和第二超极化率|γ|的超线性增加。相应的三次谐波生成 (THG) 测量是使用聚苯乙烯矩阵和可变激光波长进行的。我们得出结论，共轭长度远大于 5 个重复单元。

  DOI：

  10.1002/1099-0690(200112)2001:23<4431::aid-ejoc4431>3.0.co;2-j

文献信息

• Monodisperse Oligo(2,5-dipropoxy-1,4-phenyleneethynylene)s
  作者：Dirk Ickenroth、Silke Weissmann、Norbert Rumpf、Herbert Meier

  DOI：10.1002/1099-0690(200208)2002:16<2808::aid-ejoc2808>3.0.co;2-u

  日期：2002.8

  Oligo(phenyleneethynylene)s 1 are rod-like compounds with undisturbed conjugation. In supplementation of the previously described members of this series 1a−e, with repeating units of up to n = 5, this work contains the preparation of higher oligomers 1f−i (n = 6, 7, 8, 10) through the use of the Sonogashira−Hagihara reaction. Both the absorption and the fluorescence bands showed convergence for increasing

  低聚(亚苯基乙炔基) 1 是具有不受干扰的共轭的棒状化合物。作为对该系列 1a-e 之前描述的成员的补充，重复单元高达 n = 5，这项工作包含通过使用以下方法制备更高的低聚物 1f-i (n = 6, 7, 8, 10)园头-萩原反应。随着 n 值的增加，吸收带和荧光带均显示收敛，在有效共轭长度 nECL = 10 时达到极限值。 (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Alkyloxy substituted organic dyes for high voltage dye-sensitized solar cell: Effect of alkyloxy chain length on open-circuit voltage
  作者：Soo-Byung Ko、An-Na Cho、Mi-Jeong Kim、Chang-Ryul Lee、Nam-Gyu Park

  DOI：10.1016/j.dyepig.2011.10.014

  日期：2012.7

  Three novel organic dyes (SB1, SB2, and SB3) containing 4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-phenylaniline as electron donor and cyanoacrylic acid as electron acceptor bridged by alkyloxy (methyl = SB1, propyl = SB2 and hexyl = SB3) substituted p-phenylenevinylene linkers have been synthesized. Density functional theory (DFT) has employed to study electron distribution and intramolecular charge transfer. Increase in alkyl chain length in alkyloxy substituent leads to increase in open-circuit voltage (V-OC), which is found to be related to the increased electron lifetime at open-circuit condition. Under AM 1.5 G 1 sun light illumination (100 mW/cm(2)), an optimized SB3-sensitized cell show a short-circuit photocurrent density (J(SC)) of 12.83 mA/cm(2), an open-circuit voltage (V-OC) of 0.745 V and a fill factor (FF) of 0.64, corresponding to an overall conversion efficiency (eta) of 6.12%. Little degradation in eta observed over 40 days is indicative of long-term stability of the SB-series dyes. (C) 2011 Elsevier Ltd. All rights reserved.
• Tuning the Moisture and Thermal Stability of Metal–Organic Frameworks through Incorporation of Pendant Hydrophobic Groups
  作者：Trevor A. Makal、Xuan Wang、Hong-Cai Zhou

  DOI：10.1021/cg4009224

  日期：2013.11.6

  An isostructural series of NbO-type porous metal-organic frameworks (MOFs) with different dialkoxy-substituents of formula Cu-2(TPTC-OR) (TPTC-OR = 2',5'-dialkyl}oxy-[1,1':4',1 ''-terphenyl]-3,3 '',5,5 ''-tetracarboxylate, R = Me, Et, Pr-n, (n)Hex) has been synthesized and characterized. The moisture stability of the materials has been evaluated, and a new superhydrophobic porous MOF has been identified. The relationship between pendant side chain length and thermal stability has been analyzed by in situ synchrotron powder X-ray diffraction, showing decreased thermal stability as the side chain length is increased, contradictory to thermogravimetric decomposition studies. Additionally, the four materials exhibit moderate Brunauer-Emmett Teller (BET) and Langmuir surface areas (1127-1396 m(2) g(-1) and 1414-1658 m(2) g(-1)) and H-2 capacity up to 1.9 wt % at 77 K and 1 bar.
• Detert, Heiner; Sugiono, Erli, Advanced Synthesis and Catalysis, 1999, vol. 341, # 4, p. 358 - 362
  作者：Detert, Heiner、Sugiono, Erli

  DOI：——

  日期：——
• Soluble Ferrocene Conjugates for Incorporation into Self-Assembled Monolayers
  作者：C. J. Yu、Yoochul Chong、Jon Faiz Kayyem、Michael Gozin

  DOI：10.1021/jo982392m

  日期：1999.3.1

  A series of phenylethynyl oligomers (I-V) possessing a ferrocene and thiol at each termini have been synthesized. These oligomers have been designed to overcome the inherent insolubility of this class of complexes by substitution at the phenyl groups with methyl and propoxy substituents. Several new reactions for preparing arenethiol-protected compounds are described. Interestingly, the generation of an arenethiol anion during base- or fluoride-catalyzed deprotection has been characterized.

表征谱图