2,5-bis((2-ethylhexyl)oxy)-p-xylylene-bis(diethylphosphonate) | 304891-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-bis((2-ethylhexyl)oxy)-p-xylylene-bis(diethylphosphonate)
• 英文别名: 2,5-bis(2'-ethylhexyloxy)-1,4-bis(diethylphosphonomethyl)benzene；Tetraethyl((2,5-bis((2-ethylhexyl)oxy)-1,4phenylene)bis(methylene))bis(phosphonate)；1,4-bis(diethoxyphosphorylmethyl)-2,5-bis(2-ethylhexoxy)benzene
• CAS: 304891-35-8
• 化学式: C₃₂H₆₀O₈P₂
• 分子量: 634.771
• InChiKey: ZABUZYXAJCDZSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  42
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-bis((2-ethylhexyl)oxy)-p-xylylene-bis(diethylphosphonate) 在 18-冠醚-6 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1,4-bis[(E)-2-[4-[[3,5-bis(phenylmethoxy)phenyl]methoxy]phenyl]ethenyl]-2,5-bis(2-ethylhexoxy)benzene
  参考文献：
  名称：

  Poly(benzyl ether) dendrimers with strongly fluorescent distyrylbenzene cores as the fluorophores for peroxyoxalate chemiluminescence: insulating effect of dendritic structures on fluorescent sites

  摘要：

  Poly(benzyl ether) dendrimers containing strongly fluorescent distyrylbenzene cores were synthesized, and their fluorescence and electrochemical properties as well as the action as fluorophores in the chemiluminescence reactions were investigated. While all the dendrimers exhibited almost the same properties except for their intensities, a characteristic feature due to the dendritic structure was observed in the electrochemical behaviors. In the peroxyoxalate chemiluminescence reactions using these dendrimers as fluorophores, a bimolecular interaction between the high-energy intermediates and fluorophores was established, and a decrease in the chemiluminescence intensity with an increasing generation was observed, which was connected with the insulating effect of the dendritic structures on the core. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.108
• 作为产物：
  描述：

  1,4-bis(bromomethyl)-2,5-bis((2-ethylhexyl)oxy)benzene 在 亚磷酸三乙酯 作用下， 反应 1.5h， 生成 2,5-bis((2-ethylhexyl)oxy)-p-xylylene-bis(diethylphosphonate)
  参考文献：
  名称：

  The Hammett correlation between distyrylbenzene substituents and chemiluminescence efficiency providing various ρ-values for peroxyoxalate chemiluminescence of several oxalates

  摘要：

  Peroxyoxalate chemiluminescence (PO-CL) was investigated using eight oxalates with various phenol moieties and the distyrylbenzene (DSB) fluorophores with various substituents. The rho-values in the Hammett correlation between the substituent constants (sigma(+)(p)) of the DSBs and the singlet chemiexcitation yields (Phi(s)) for the PO-CL reactions varied from -0.50 to -1.01 depending on the oxalate structure, and the reactive oxalates tended to afford the higher absolute rho-values but with a few exceptions. Based on the CIEEL mechanism, these experimental observations suggest that the aryloxy groups still remain in the 1,2-dioxetanones (DOTs), which are the postulated high-energy intermediates, and control the electronic properties of DOTs as electron-acceptors. The LUMO energies of the DOTs calculated by the ab initio method with a B3LYP/6-31g(d) basis set reveal that the lower the DOT-LUMO energies, the higher the absolute rho-values were provided for the corresponding oxalates, as predicted by the frontier molecular orbital (FMO) theory. Thus, the chemical species interacting with the DSBs would be not unitary and will be DOTs. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.12.006

文献信息

• CH/π-Interaction-Guided Self-Assembly in π-Conjugated Oligomers
  作者：Mahima Goel、Manickam Jayakannan

  DOI：10.1002/chem.201102670

  日期：2012.3.5

  using single‐crystal structures. OPVs were designed with appropriate pendants in the aromatic core and varied by hydrocarbon or fluorocarbon tails along the molecular axis. The roles of aromatic π‐stack, van der Waals forces, fluorophobic effect and CH/π interactions were investigated on the theromotropic liquid crystallinity of OPV molecules. Single‐crystal structures of hydrocarbon OPVs provided

  我们报告了基于低聚亚苯基亚乙烯基（OPV）的π共轭骨架中CH /π氢键驱动的自组装，并通过使用单晶结构在分子水平上追踪了相互作用的起源。OPV的设计在芳族核中带有适当的侧基，并沿分子轴的碳氢化合物或碳氟化合物尾部变化。研究了芳香族π堆积，范德华力，疏水效应和CH /π相互作用对OPV分子的热致液晶性的影响。烃类OPV的单晶结构为π环（氢键受体）和烷基CH（氢键供体）之间存在CH /π相互作用提供了直接证据。四个重要的晶体学参数d c-x = 3.79Å，θ= 21.49°，φ = 150.25°，d Hp-x = 0.73Å，根据典型的CH /π相互作用进行匹配。CH /π相互作用促进了x - y平面中液晶元的紧密堆积，并进一步沿c方向突出轴产生层状结构。在没有CH /π相互作用的情况下，范德华相互作用使装配趋向于Schlieren向列织构。碳氟化合物OPV表现出近晶液晶结构，进一步经历了Smectic
• Poly[(arylene ethynylene)-<i>alt</i>-(arylene vinylene)]s Based on Anthanthrone and Its Derivatives: Synthesis and Photophysical, Electrochemical, Electroluminescent, and Photovoltaic Properties
  作者：Suru Vivian John、Věra Cimrová、Christoph Ulbricht、Veronika Pokorná、Aleš Růžička、Jean-Benoit Giguère、Antoine Lafleur-Lambert、Jean-François Morin、Emmanuel Iwuoha、Daniel Ayuk Mbi Egbe

  DOI：10.1021/acs.macromol.7b02136

  日期：2017.11.14

  of copolymers (P1–P5) based on poly[(arylene ethynylene)-alt-(arylene vinylene)]s backbone (−Ph–C≡C–Anth–C≡C–Ph–CH═CH–Ph–CH═CH−)n. During the synthesis of P1–P5, different alkyloxy side chains were incorporated in order to tune the properties of the polymers. Of the copolymer series only P1 (containing anthanthrone and branched 2-ethylhexyloxy side chains on phenylenes), P2 and P3 (for which the anthanthrones

  蒽酮及其衍生物是大型多环芳族化合物（PAC），对于将其掺入可溶性共轭聚合物的结构提出了许多挑战。首次，这组PAC的被用作用于共聚物（合成的构建块P1 - P5）基于聚[（亚芳基亚乙炔基） - ALT - （亚芳基亚乙烯基）] S骨架（-Ph-C≡C –Anth–C≡C–Ph–CH═CH–Ph–CH═CH-）n。在P1 - P5的合成过程中，为了调节聚合物的性能，引入了不同的烷氧基侧链。在共聚物系列中，只有P1（在蒽上含有蒽酮和支链的2-乙基己氧基侧链），P2及P3（其为含羰基的蒽嵌蒽醌转化为蒽嵌蒽含烷氧基取代基）是可溶的。报道了P1 - P3的光物理，电化学，电致发光和光伏特性，并就侧链的影响进行了比较和讨论。
• Sequence-Independent Synthesis of π-conjugated Arylenevinylene Oligomers using Bifunctional Thiophene Monomers
  作者：Kammasandra Nanjunda Shivananda、Irit Cohen、Elena Borzin、Yulia Gerchikov、Michal Firstenberg、Olga Solomeshch、Nir Tessler、Yoav Eichen

  DOI：10.1002/adfm.201101897

  日期：2012.4.10

  Sequence‐independent or “click” chemistry is applied for the preparation of a series of novel and structurally similar π‐conjugated oligomers. The new oligomers are prepared using Wittig–Horner chemistry from bifunctional building blocks that can be interconnected to one another at any desired sequence. The bifunctional building blocks consist of aromatic skeletons with acetal protected aldehyde groups

  序列无关或“点击”化学用于制备一系列新颖且结构相似的π共轭低聚物。新的低聚物是使用Wittig-Horner化学方法从双功能结构单元制备的，该结构单元可以按任何所需的顺序相互连接。双官能结构单元由具有在一侧上和膦酸二酯基团受保护的缩醛的醛基芳香族骨架的对位到醛官能团。形成亚芳基亚乙烯基的第一步是将功能化醛与双功能单体的甲基膦酸酯叶立德进行维蒂希-霍纳偶联。采用分步保护-去保护过程制备结构相似的π共轭低聚亚苯基亚乙烯基。制备并表征了新的二，三，五和七亚苯基亚乙烯基。选定的五亚芳基亚乙烯基被纳入有机场效应晶体管中作为半导体通道。
• Side Chain Effects in Hybrid PPV/PPE Polymers
  作者：Daniel Ayuk Mbi Egbe、Carsten Peter Roll、Eckhard Birckner、Ulrich-Walter Grummt、Regina Stockmann、Elisabeth Klemm

  DOI：10.1021/ma012195g

  日期：2002.5.1

  long linear alkoxy, e.g., dodecyloxy, octadecyloxy, or branched alkoxy side chains, e.g., 2-ethylhexyloxy, on the conjugated backbone. Thermotropic and lyotropic liquid crystalline behavior was observed with polarized optical microscopy. The presence of triple bonds along the PPV backbone increases the electron affinity of these polymers, which is reflected by the comparatively (with MEH−PPV) higher

  发光体二醛1和2与双膦酸酯3的霍纳-沃兹沃思-埃蒙斯烯化反应可提供具有明确定义的一般结构的高分子量且热稳定的PPV / PPE杂化聚合物4和5-（CH CH-Ph-CH CH- Ph-C⋮C-Ph-C⋮C-Ph-）n，已通过NMR，红外和元素分析证实。将长链状烷氧基（例如十二烷氧基，十八烷氧基）或支链烷氧基侧链（例如2-乙基己氧基）连接到共轭主链上后，即可获得可溶性且良好的成膜材料。用偏光光学显微镜观察了热致和溶致液晶行为。沿着PPV主链的三键的存在增加了这些聚合物的电子亲和力，这相对于（使用MEH-PPV）相对于Ag / AgCl较高的1.30 V氧化电势反映出来。聚合物4和5是良好的光电导和高发光材料。虽然所有4型聚合物的光物理行为几乎相同（λmax，abs在稀氯仿溶液中获得450 nm，λmax，em = 490 nm）或5（λmax，abs = 470 nm，λmax，em = 553
• π-Conjugate Fluorophore-Tagged and Enzyme-Responsive <scp>l</scp>-Amino Acid Polymer Nanocarrier and Their Color-Tunable Intracellular FRET Probe in Cancer Cells
  作者：Sonashree Saxena、Manickam Jayakannan

  DOI：10.1021/acs.biomac.7b00710

  日期：2017.8.14

  l-aspartic acid monomer to yield OPV-tagged amphiphilic luminescent polyesters. These amphiphilic polyesters self-assembled through strong aromatic π–π stacking and hydrophilic/hydrophobic noncovalent forces into <200 nm size blue-luminescent nanoparticles in aqueous medium. The OPV-tagged polymer nanoparticles served as FRET donor and encapsulated water insoluble Nile Red (NR) fluorophore as a FRET acceptor

  本研究说明了用于癌细胞中颜色可调细胞内生物成像的酶促反应和π-共轭标签的1-氨基酸两亲聚合物及其荧光共振能量转移（FRET）探针的第一个实例。熔融聚合的寡亚苯基亚乙烯基（OPV）π共轭二醇是量身定制，并进行与多官能热选择性熔融酯交换反应升-天冬氨酸单体可制得带有OPV标签的两亲发光聚酯。这些两亲性聚酯通过强芳族π-π堆积和亲水/疏水非共价作用力自组装成水性介质中小于200 nm的蓝色发光纳米粒子。带有OPV标签的聚合物纳米粒子充当FRET供体，封装的水不溶性尼罗红（NR）荧光团充当FRET受体。详细的光物理研究表明，OPV和NR均被限制在聚合物纳米容器的Förster距离内，并且纳米域为从OPV到NR的有效激发能转移提供了适当的几何形状。乳腺癌的细胞毒性研究（MCF 7），宫颈癌（HeLa）和正常（野生型MEF）细胞系显示，新生的发光OPV纳米颗粒和OPV-NR FRET探针均对高达100μg/