4-iodo-2,5-bis(octyloxy)benzaldehyde | 186358-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-iodo-2,5-bis(octyloxy)benzaldehyde
• 英文别名: 4-iodo-2,5-bis-octyloxy-benzaldehyde；2,5-dioctyloxy-4-iodobenzaldehyde；4-Iodo-2,5-dioctyloxybenzaldehyde；4-iodo-2,5-dioctoxybenzaldehyde
• CAS: 186358-39-4
• 化学式: C₂₃H₃₇IO₃
• 分子量: 488.449
• InChiKey: XBLXIWSNVRTGAD-UHFFFAOYSA-N

物化性质

• 熔点：
  71.5 °C(Solv: hexane (110-54-3))
• 沸点：
  536.8±50.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-iodo-2,5-bis(octyloxy)benzaldehyde 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三苯基膦 、 锌 作用下， 以 二氯甲烷 、 三乙胺 为溶剂， 反应 61.0h， 生成 {{4-{[4-(2,2-dibromoethenyl)-2,5-bis(octyloxy)phenyl]ethynyl}-2,5-bis(octyloxy)phenyl}ethynyl}triisopropylsilane
  参考文献：
  名称：

  合成低聚（苯乙炔二基）衍生物的新迭代方法及其在制备富勒烯-低聚（苯乙炔二基）缀合物作为活性光伏材料中的应用

  摘要：

  使用以下反应顺序，通过迭代方法由2,5-双（辛氧基）-4-[（三异丙基甲硅烷基）乙炔基]苯甲醛（5）制备双对称取代的oligo（phenyleneethynediyl）（OPE）衍生物：i）Corey-Fuchs二溴代烯烃反应，ii）用过量的二异丙基氨基锂处理，和iii）将所得的末端炔与2,5-二碘-1,4-双（辛氧基）苯（3）进行金属催化的交叉偶联反应（方案2和3）。3）。如此获得的OPE二聚体8和三聚体13与N-甲基甘氨酸和C 60的反应在回流的甲苯中分别得到相应的C 60 OPE共轭物16和17（方案4）。另一方面，用Bu 4 N处理受保护的末端炔烃8和13，然后使所得的9和14与4-碘-N，N-二丁基苯胺在Sonogashira条件下反应，分别得到10和15（方案2和3）。3）。随后用N-甲基甘氨酸和C 60进行治疗在回流的甲苯中，提供了C 60 OPE衍生物18和19（方案4）。

  DOI：

  10.1002/hlca.200490266
• 作为产物：
  描述：

  对苯二酚 在 potassium iodate 、 正丁基锂 、 硫酸 、 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成 4-iodo-2,5-bis(octyloxy)benzaldehyde
  参考文献：
  名称：

  合成低聚（苯乙炔二基）衍生物的新迭代方法及其在制备富勒烯-低聚（苯乙炔二基）缀合物作为活性光伏材料中的应用

  摘要：

  使用以下反应顺序，通过迭代方法由2,5-双（辛氧基）-4-[（三异丙基甲硅烷基）乙炔基]苯甲醛（5）制备双对称取代的oligo（phenyleneethynediyl）（OPE）衍生物：i）Corey-Fuchs二溴代烯烃反应，ii）用过量的二异丙基氨基锂处理，和iii）将所得的末端炔与2,5-二碘-1,4-双（辛氧基）苯（3）进行金属催化的交叉偶联反应（方案2和3）。3）。如此获得的OPE二聚体8和三聚体13与N-甲基甘氨酸和C 60的反应在回流的甲苯中分别得到相应的C 60 OPE共轭物16和17（方案4）。另一方面，用Bu 4 N处理受保护的末端炔烃8和13，然后使所得的9和14与4-碘-N，N-二丁基苯胺在Sonogashira条件下反应，分别得到10和15（方案2和3）。3）。随后用N-甲基甘氨酸和C 60进行治疗在回流的甲苯中，提供了C 60 OPE衍生物18和19（方案4）。

  DOI：

  10.1002/hlca.200490266

文献信息

• Synthesis, characterization, and electroluminescence of polyfluorene copolymers containing T-shaped isophorone derivatives
  作者：Moo-Jin Park、Jonghee Lee、In Hwan Jung、Jong-Hwa Park、Hoyoul Kong、Ji-Young Oh、Do-Hoon Hwang、Hong-Ku Shim

  DOI：10.1002/pola.23761

  日期：2010.1.1

  phenyl, and isophorone, we introduced three individual segments of an isophorone derivative containing two cyanide groups at the carbonyl position, a dialkoxy phenyl group for increased solubility, and a triphenyl amine for effective charge transfer. Furthermore, we introduced vinyl linkages between each segment to increase the length of π‐conjugation. The synthesized polyfluorene copolymers with the

  我们已经成功合成了一系列新的芴基共聚物，即聚[（9,9-双（4-辛氧基-苯基）芴-2,7-二基）-共聚物‐ [2（3 2 [4（2 4 [双（溴苯基-4-基）氨基]苯基}乙烯基）-2-，5-双辛氧基苯基]乙烯基} ‐5,5-二甲基-环己基-2-烯基）丙二腈] （PFTBMs），具有低能带隙共聚单体2（3 2 [4（2 4 [bis（4-（4-溴苯基）氨基]苯基]乙烯基）−2,5-双辛基氧基苯基]乙烯基}}的摩尔比-5,5-二甲基-环己-2-烯基）丙二腈（BTBM）。为了由三苯胺，二烷氧基苯基和异佛尔酮制备BTBM（具有T形结构），我们引入了异佛尔酮衍生物的三个独立部分，在羰基位置包含两个氰基，一个用于增加溶解度的二烷氧基苯基和一个三苯基异佛尔酮衍生物胺进行有效的电荷转移。此外，我们在每个片段之间引入了乙烯基键，以增加π共轭的长度。合成的聚芴共聚物与BTBM，PFTBM，通过钯催化的
• Synthesis of dumbbell-shaped bis-(pyrazolino[60]fullerene)-oligophenylenevinylene derivatives
  作者：Marı́a J. Gómez-Escalonilla、Fernando Langa、Jean-Michel Rueff、Laurence Oswald、Jean-François Nierengarten

  DOI：10.1016/s0040-4039(02)01769-0

  日期：2002.10

  Symmetrically substituted oligophenylenevinylene (OPV) derivatives bearing terminal p-nitrophenyl-hydrazone groups have been prepared and used for the synthesis of dumbbell-shaped bis-(pyrazolino[60]fullerene)-OPV systems.

  制备了带有末端对硝基苯基-基团的对称取代的低聚亚苯基亚乙烯基（OPV）衍生物，并将其用于合成哑铃形的双-（吡唑并[60]富勒烯）-OPV体系。
• Pyrazolino[60]fullerene-Oligophenylenevinylene Dumbbell-Shaped Arrays: Synthesis, Electrochemistry, Photophysics, and Self-Assembly on Surfaces
  作者：Fernando Langa、Maria J. Gomez-Escalonilla、Jean-Michel Rueff、Teresa M. Figueira Duarte、Jean-François Nierengarten、Vincenzo Palermo、Paolo Samorì、Yannick Rio、Gianluca Accorsi、Nicola Armaroli

  DOI：10.1002/chem.200500089

  日期：2005.7.18

  oligophenylenevinylene (OPV) derivatives bearing terminal p-nitrophenylhydrazone groups have been prepared and used for the synthesis of dumbbell-shaped bis(pyrazolino[60]fullerene)-OPV systems. In these triad arrays, the OPV-type fluorescence is dramatically quenched as a consequence of ultrafast OPV-->C60 singlet energy transfer. In its turn the fullerene singlet state is quenched by pyrazoline-->C60 electron

  已经制备了带有末端对硝基苯基hydr基团的对称取代的低聚亚苯基亚乙烯基（OPV）衍生物，并将其用于合成哑铃形的双（吡唑并[60]富勒烯）-OPV体系。在这些三单元组阵列中，由于超快的OPV-> C60单线态能量转移，OPV型荧光显着淬灭。反过来，与相应的参考富勒烯分子的行为相一致，富勒烯单重态被吡唑啉-> C60电子转移淬灭。通过在CH2Cl2中在77 K时富勒烯荧光的恢复以及在298 K中在甲苯中的富勒烯荧光的恢复，证明了多组分阵列中电子转移的发生。在这些条件下，OPV-> C60的能量转移不受影响。事实证明，对于OPV三聚体，此过程的速率要比相应的五聚OPV阵列高。这与能量转移理论的预期相符。扫描隧道显微镜（STM）和扫描力显微镜（SFM）表明，双（吡唑啉并[60]富勒烯）-OPV可以在高度取向的热解石墨的基面上自组装成有序的层状晶体结构。
• Synthesis, Morphology, and Optical Properties of Tetrahedral Oligo(phenylenevinylene) Materials
  作者：Shujun Wang、Warren J. Oldham、Raymond A. Hudack,、Guillermo C. Bazan

  DOI：10.1021/ja992924w

  日期：2000.6.1

  A novel topological strategy is described for designing amorphous molecular solids suitable for optoelectronic applications. In this approach, chromophores are attached to a tetrahdral point of convergence. Stilbenoid units were covalently linked to tetraphenylmethane, tetraphenyladamantane, or tetraphenylsilane cores using palladium catalyzed coupling methodology, Thus, reaction of E(C6H5X)(4) (E = C and adamantane, X = I; E = Si, X = Br) with styrene or 4,3'-tert-butylvinylstilbene under Heck coupling conditions yields the corresponding tetrakis(stillbenyl) (E(STB)(4)) and tetrakis(4-tert-butyIstyrylstilbenyl) (E((BuSSB)-Bu-t)(4)) compounds. Similarly, reaction of 1,1-diphenyl-2-(4-dihydroxyboronphenyl)ethene or 2-(4-pinacolatoboronphenyl)-3,3-diphenylacrylonitrile with tetrakis(4-bromophenyl)methane using Suzuki coupling methodology gives tetrakis(4,4'-(2,2-diphenyl-vinyl)-1,1'-biphenyl (C(DPVBi)(4)) or tetrakis(4,4'-(3,3-diphenylacrylonitrile biphenyl)methane (C(DPAB)(4)), respectively, in good yields. Compounds with more extended conjugation can also be prepared. Thus, reaction of excess 1-(4'-tert-butylstyryl)-4-(4'-vinylstyryl)benzene with C(C6H4I)(4) provides tetrakis(4-(4'-(4"-tert-butylstyryl)styryl)stilbenyl)methane (C(4R-Bu-t)(4)) in low yield (similar to 20%). The more soluble analogue, tetrakis(4-(4'-(3",5"-di-tert-butylstyryl)stilbenyl)methane (C(4R-2(t)Bu)(4)) is prepared similarly using 1-(3',5'-di-tert-butylstyryl)-4-(4'-vinylstyryl)benzene and in better yield (similar to 80%). Alkoxy substituents can also be used to increase solubility. Tetrakis((4-(2',5'-dioctyloxy-4'-styryl)styryl)stilbenyl)methane methane, C(4R-(OC8H17)(2))(4), was prepared by treatment of C(C6H4I)(4) with excess 2,5-dioctyloxy-1-styryl-4(4'-vinylstyryl)benzene (yield similar to 73%). The simple stilbenyl-derivatives were found by DSC measurements and powder diffraction experiments to be crystalline compounds. Comparison of single-crystal X-ray diffraction data shows that C(STB)(4) and Si(STB)(4) form isomorphous crystals. The larger E((BuSSB)-Bu-t)4, C(DPVBi)(4), and C(DPAB)(4) compounds readily form amorphous glasses with elevated glass transition temperatures (T-g = 142-190 degrees C) in the absence of solvent. Extending the conjugation length of the arm leads to more stable glasses. For example, the glass transition temperature of C(4R-Bu-t)(4) was measured at 230 degrees C. Solution phase optical spectroscopic data of E((BuSSB)-Bu-t)(4) (E = C, adamantane, and Si) are characteristic of the parent distyrylbenzene chromophore. Films, however, show broad and significantly red-shifted emission spectra. In contrast, C(DPVBi)(4) gives absorption and emission spectra which are nearly identical between dilute solution phase samples and neat solid films. The emission of C(DPAB)(4) is broad and structureless, reminiscent of exciplex or excimer emission. Films of the tetramers with longer arms (C(4R-Bu-t)(4), C(4R-2(t)Bu)(4), and C(4R-(OC8H17)(2))(4)) show emission properties which are dependent on sample history. Annealing the sample at elevated temperature leads to red-shifted emission as a result of better interdigitation between the optically active fragments.
• Synthesis of fullerene–oligophenyleneethynylene hybrids
  作者：Tao Gu、Jean-François Nierengarten

  DOI：10.1016/s0040-4039(01)00384-7

  日期：2001.4

  Disymmetrically substituted oligophenyleneethynylene (OPE) derivatives have been prepared by a new iterative method and attached to C, by a 1,3-dipolar cycloaddition of the azomethine ylides generated in situ from the corresponding OPE aldehydes and sarcosine. (C) 2001 Published by Elsevier Science Ltd.