2,5-bis(3-[N,N-diethylamino]-1-oxapropyl)-1,4-diiodobenzene | 845672-69-7

• 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(3-[N,N-diethylamino]-1-oxapropyl)-1,4-diiodobenzene
• 英文别名: 2,2'-((2,5-diiodo-1,4-phenylene)bis(oxy))bis(N,N-diethylethanamine)；2-[4-[2-(diethylamino)ethoxy]-2,5-diiodophenoxy]-N,N-diethylethanamine
• CAS: 845672-69-7
• 化学式: C₁₈H₃₀I₂N₂O₂
• 分子量: 560.257
• InChiKey: NTVVNRNEXAGUTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-bis(3-[N,N-diethylamino]-1-oxapropyl)-1,4-diiodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 copper(l) iodide 、 二异丙胺 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 1,4-diethynyl-2,5-bis[3-(N,N-diethylamino)-1-oxapropyl]benzene
  参考文献：
  名称：

  Water-Soluble Cationic Poly(p-phenyleneethynylene)s (PPEs):  Effects of Acidity and Ionic Strength on Optical Behavior

  摘要：

  Three cationic PPEs P1 '-P3 ' were obtained through quaternization of their neutral polymers, of which all side chains were respectively featured with a tertiary amino group (P1), an alternative tertiary amino and tri(ethylene glycol)methyl ether group (P2), and an alternative tertiary amino and dodecyloxy group (P3). P1 ' showed intrinsic water-solubility although its quaternization degree was only 45%. Slightly blue-shifted UV-vis absorption maxima in an acidic environment (maximal Delta lambda(max) approximate to 3 nm) and obvious red-shifted absorption (maximal Delta lambda(max) approximate to 30 nm) and emission maxima (maximal Delta lambda(max) approximate to 20 nm) in an alkaline environment at pH < 13 are explained in terms of pH-induced planarization of the conjugated backbone. After the pH was increased to 14, a new absorption (lambda(max) approximate to 478 nm) and emission (lambda(max) approximate to 495 nm) peak appeared in the redder region and the fluorescence intensity further dramatically decreased, implying the occurrence of the conformational change from the planarization of conjugated backbone to the interchain aggregation. The fluorescence enhancement of P1 ' in an acidic environment and the fluorescence decrease of P1 ' in an alkaline environment are attributed to the pH-influenced quenching ability of the nonbonding electron pair on the nitrogen atom, which belongs to the unquaternized tertiary amino group on the side chain, and the interchain aggregation. Such pH-influenced fluorescence intensity can be efficiently buffered by adding salts at pH < 10. Although adding salts in a neutral environment only creates the planarization of PPE conjugated backbone, adding salts in an alkaline environment significantly promotes the formation of interchain aggregation. Amplified quenching of P1 ' by anionic quencher Fe(CN)(6)(4-) was observed and its K-sv increased significantly after adding salts or increasing pH to 14, for example from K-sv = 9.6 x 10(5) M-1 at pH = 7 to 7.7 x 10(6) M-1 at pH = 10 when [NaCl] = 0.1 M, due to the formation of elongated pi-conjugation.

  DOI：

  10.1021/ma048717k
• 作为产物：
  描述：

  对苯二甲醚 在 硫酸 、 碘 、 三溴化硼 、 碘酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 72.0h， 生成 2,5-bis(3-[N,N-diethylamino]-1-oxapropyl)-1,4-diiodobenzene
  参考文献：
  名称：

  近红外发射BODIPY基共轭聚合物的合成与表征

  摘要：

  通过钯催化的Sonogashira偶联反应可以合成三种基于BODIPY的新型共轭聚合物。与BODIPY模型衍生物相比，该聚合物可以发射深红色至近红外区域，发射光谱最大值在λ= 640-660 nm处，并具有0.23至0.26的中等荧光量子产率。对三个聚合物重复单元进行密度泛函理论（DFT）计算，并估算了共轭聚合物的HOMO和LUMO能级。 有机硼染料-共轭聚合物-BODIPY-近红外

  DOI：

  10.1055/s-0031-1290364

文献信息

• Chiral sensing for induced circularly polarized luminescence using an Eu(iii)-containing polymer and d- or l-proline
  作者：Fengyan Song、Guo Wei、Xiaoxiang Jiang、Fei Li、Chengjian Zhu、Yixiang Cheng

  DOI：10.1039/c3cc42323a

  日期：——

  An Eu(III)-containing polymer can exhibit intense induced circularly polarized luminescence (CPL) in the presence of proline. In addition, the optical anisotropy factor (glum) of the polymer for 5D0 → 7F1/7F2 transition was much higher than that of a single model molecule, which reveals the amplification effect of CPL arising from the conjugated polymer structure.

  一种含有Eu(III)的聚合物在存在脯氨酸的情况下可以展现出强烈的诱导圆偏振发光（CPL）。此外，该聚合物对于5D0 → 7F1/7F2跃迁的光学各向异性因子（glum）远高于单一模型分子，这揭示了由共轭聚合物结构引起的CPL放大效应。
• A highly selective fluorescent sensor for Hg2+ based on the water-soluble poly(p-phenyleneethynylene)
  作者：Jie Li、Jie Meng、Xiaobo Huang、Yixiang Cheng、Chengjian Zhu

  DOI：10.1016/j.polymer.2010.05.038

  日期：2010.7

  responsive optical properties of P-1 and P-2 on Hg2+ were investigated by fluorescence spectra. Hg2+ can lead to nearly complete fluorescence quenching of P-1. On the contrary, Hg2+ can show the most pronounced fluorescence enhancement response of P-2 in aqueous solution without interference from those coexistent ions, such as K+, Mg2+, Pb2+, Co2+, Ni2+, Ag+, Cd2+, Cu2+, Fe3+ and Zn2+. The results also

  共轭聚合物P-1可以通过4,7-二乙炔基-苯并[2,1,3]噻二唑（M-1）和1,4-双[3'-（N，N-二乙氨基）的聚合反应合成-1'-氧杂丙基] -2,5-二碘代苯（M-2）通过Pd催化的Sonogashira反应。水溶性共轭聚电解质P-2可以通过P-1与溴乙烷的反应获得。两个P-1和P-2可以发射橙色荧光。通过荧光光谱研究了P-1和P-2在Hg 2+上的响应光学性质。汞2+可以导致P-1几乎完全被荧光猝灭。相反，Hg 2+可以显示水溶液中P-2的最明显的荧光增强反应，而不受这些共存离子（如K +，Mg 2 +，Pb 2 +，Co 2 +，Ni 2+， Ag +，Cd 2 +，Cu 2 +，Fe 3+和Zn 2+。结果还表明，这种水溶性共轭聚电解质可以用作水中Hg 2+检测的高灵敏度和选择性荧光传感器。
• A novel cationic conjugated polymer for homogeneous fluorescence-based DNA detection
  作者：Hui Peng、Christian Soeller、Jadranka Travas-Sejdic

  DOI：10.1039/b607293c

  日期：——

  A novel water-soluble cationic conjugated polymer, poly(2,5-bis[3-(N,N-diethylamino)-1-oxapropyl]-para-phenylenevinylene}-alt-para-phenylenevinylene) dibromide, was synthesized and used to develop a simple label-free DNA detection essay.

  一种新型的水溶性阳离子共轭聚合物——聚(2,5-双[3-(N,N-二乙氨基)-1-氧丙基]-对亚苯基亚乙烯基}-交替-对亚苯基亚乙烯基)二溴化物被合成，并用于开发一种简便的无标记DNA检测方法。
• Amplified Fluorescence Quenching and Electroluminescence of a Cationic Poly(<i>p</i>-phenylene-<i>c</i><i>o</i>-thiophene) Polyelectrolyte
  作者：Michael B. Ramey、Hille、Michael F. Rubner、Chunyan Tan、Kirk S. Schanze、John R. Reynolds

  DOI：10.1021/ma048360k

  日期：2005.1.1

  developed that displays significant fluorescence quenching (25% quenching of polymer's fluorescence at quencher concentrations of 500 nM) and forms well-defined multilayer structures via electrostatic deposition. The polymer contains alternating 2,5-thienyl- and 2,5-bis[2-(N,N-diethylamine)-1-oxapropyl]-substituted 1,4-phenylene units formed by a Stille reaction protocol. Poly(2,5-bis[2-(N,N-diethylamino)-1-oxapropyl]-1

  开发了一种水溶性共轭聚合物，该聚合物显示出显着的荧光猝灭（在500 nM的猝灭剂浓度下，聚合物荧光的25％猝灭），并通过静电沉积形成定义明确的多层结构。该聚合物包含通过Stille反应方案形成的交替的2，5-噻吩基-和2，5-双[2-（N，N-二乙胺）-1-氧丙基]-取代的1，4-亚苯基单元。聚（2,5-双[2-（N，N-二乙基氨基）-1-氧杂丙基] -1,4-亚苯基} - ALT -2,5-亚噻吩基）（PPT-NET 2）在80％，合成2,5-双（三甲基锡烷基）噻吩和反应性二碘化物种2,5-双（3- [ N，N-二乙氨基] -1-氧丙基）-1,4-二碘苯。中性聚合物可溶于THF，氯仿和1 M HCl（水溶液）。通过GPC（相对于聚苯乙烯标准）测得数均分子量为5300g mol -1（约40个环）。PPT-NET 2被容易地转化为水溶性聚合物，聚2,5-双[2-（N，N，N- -tri
• Inner salt-shaped small molecular photosensitizer with extremely enhanced two-photon absorption for mitochondrial-targeted photodynamic therapy
  作者：Wenbo Hu、Tingchao He、Rongcui Jiang、Jun Yin、Lin Li、Xiaomei Lu、Hui Zhao、Lei Zhang、Ling Huang、Handong Sun、Wei Huang、Quli Fan

  DOI：10.1039/c6cc09473b

  日期：——

  An inner salt-shaped small-molecular photosensitizer with unprecedentedly strong two-photon absorption was developed for highly efficient two-photon photodynamic therapyviaa mitochondrial apoptosis pathway.

  开发了一种内盐形态的小分子光敏剂，具有前所未有的强双光子吸收能力，可通过线粒体凋亡途径，实现高效的双光子光动力治疗。