2,5-dibromo-1,4-bis[2-[2-(2-bromoethoxy)ethoxy]ethoxyl]benzene | 952070-61-0

• 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-dibromo-1,4-bis[2-[2-(2-bromoethoxy)ethoxy]ethoxyl]benzene
• 英文别名: 1,4-bis(2-(2-(2-bromoethoxy)ethoxy)ethoxy)-2,5-dibromobenzene；1,4-dibromo-2,5-di[2-[2-(2-bromoethoxy)ethoxy]ethoxyl]benzene；1,4-Dibromo-2,5-bis[2-[2-(2-bromoethoxy)ethoxy]ethoxy]benzene；1,4-dibromo-2,5-bis[2-[2-(2-bromoethoxy)ethoxy]ethoxy]benzene
• CAS: 952070-61-0
• 化学式: C₁₈H₂₆Br₄O₆
• 分子量: 658.017
• InChiKey: UUHDEAPVHRDGHP-UHFFFAOYSA-N

物化性质

• 熔点：
  46-48 °C
• 沸点：
  603.8±55.0 °C(Predicted)
• 密度：
  1.701±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-dibromo-1,4-bis[2-[2-(2-bromoethoxy)ethoxy]ethoxyl]benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 反应 16.0h， 生成
  参考文献：
  名称：

  Water-soluble hyperbranched poly(phenyleneethynylene)s: Facile synthesis, characterization, and interactions with dsDNA

  摘要：

  Two novel water-soluble hyperbranched poly(p-phenyleneethynylene)s (HBP1' and HBP2') bearing different contents of oligo(ethylene oxide) (OEO) side chains with ammonium end groups were synthesized by the facile "A(2) + B-2 (or A(2)') + C-3" protocol based on Sonogashira polymerization. Their linear analog (LP2') was also synthesized for comparative investigation. The optical properties of the neutral precursory polymers in THF and final cationic conjugated polyelectrolytes (CCPs) in aqueous solution were studied. Compared with LP2', HBP1' exhibited increased water solubility and fluorescence quantum yield despite its lower charge density, and HBP2', with the similar charge density as LP2', showed the best water solubility and the highest fluorescence quantum yield among the three CCPs. This indicated that the introduction of hyperbranched structure into conjugated polyelectrolytes was an efficient way to improve water solubility and fluorescence quantum yield because intermolecular aggregation was remarkably prevented. The interactions among the three CCPs and double-stranded DNA (dsDNA) were studied using ethidium bromide (EB) as the fluorescent probe. The electrostatic bindings of the three CCPs with dsDNA/EB complex resulted in displacement of EB from dsDNA to the solution accompanied by the quenching of EB fluorescence. Both HBP1' and HBP2' bound to dsDNA more efficiently than LP2', and HBP2' formed the most stable complex with dsDNA, suggesting that dsDNA might enter the cavities of single-molecular globular architectures of these hyperbranched conjugated polyelectrolytes and induced additional host-guest spatial interactions. Hence, HBP1' and HBP2' may be proved very useful in gene delivery or DNA biosensor applications. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2014.12.068
• 作为产物：
  描述：

  1,4-dibromo-2,5-di[2-[2-(2-tosylethoxy)ethoxy]ethoxyl]benzene 在 lithium bromide 作用下， 以 丙酮 为溶剂， 以64.3%的产率得到2,5-dibromo-1,4-bis[2-[2-(2-bromoethoxy)ethoxy]ethoxyl]benzene
  参考文献：
  名称：

  用于DNA浓度测定的阳离子共轭聚电解质的设计

  摘要：

  阳离子共轭聚电解质 poly110 和 poly120 被设计、合成和表征，具有测定双链 DNA 浓度 [dsDNA] 的预期功能。它们的结构包含一个由亚苯基-芴链段与 2,1,3-苯并噻二唑 (BT) 单元共聚的 pi 离域光学活性主链和带电的侧基，在水中具有极好的溶解性。poly1x 中的下标是指链中 BT 单元的摩尔百分比。将 dsDNA 添加到 poly110 或 poly120 会导致发射颜色从蓝色变为绿色。可以处理这些光谱变化以获得参数 delta，该参数可用于生成指示 [dsDNA] 的校准曲线。光致发光光谱分析表明，dsDNA 添加导致从蓝色发射段到 BT 位点的更有效的 FRET、BT 发射量子产率的增加和亚苯基-芴段的部分猝灭。还进行了研究以最大化 [dsDNA] 测定的范围。我们发现，通过结合来自两个不同初始浓度 poly110 的响应，可以生成响应超过 7 个数量级的

  DOI：

  10.1021/ja072471s

文献信息

• Synthesis and Characterization of Water-Soluble Conjugated Glycopolymer for Fluorescent Sensing of Concanavalin A
  作者：Jianbing Shi、Liping Cai、Kan-Yi Pu、Bin Liu

  DOI：10.1002/asia.200900297

  日期：2010.2.1

  polymerization. A cationic conjugated polymer A and an α‐mannose‐bearing polymer B are subsequently obtained through different post‐polymerization methods. As a result of the charged pendant groups or sugar‐bearing groups attached to the polymer side chains, both A and B show good water‐solubility. The titration of Concanavalin A (Con A) into polymer aqueous solution leads to different fluorescent responses for

  通过Suzuki交叉偶联聚合反应合成了一种中性的聚芴衍生物，其中含有20 mol％的2,1,3-苯并噻二唑（BT）。随后通过不同的后聚合方法获得了阳离子共轭聚合物A和带有α-甘露糖的聚合物B。由于连接到聚合物侧链的带电侧基或含糖基团，A和B均显示出良好的水溶性。伴刀豆球蛋白A（Con A）在聚合物水溶液中的滴定导致聚合物A和B的荧光响应不同。聚合物A与Con A相互作用后未显示任何明显的荧光变化，而聚合物B显示当添加Con A时BT发射强度的荧光增加。这是由于α-甘露糖与Con A之间的特定相互作用，该相互作用诱导聚合物聚集，然后促进能量从亚苯基-芴链段转移至BT单元。通过将BT发射强度的变化与Con A浓度相关联，可以获得1 n M至250 n M的实用校准曲线。基于聚合物B的Con A大分子探针的优势在于，它在Con A识别后显示信号增加，这与其他基于共轭聚合物的荧光猝灭测定法明显不同。
• Water-soluble hyperbranched poly(phenyleneethynylene)s: Facile synthesis, characterization, and interactions with dsDNA
  作者：Yan-Qin Huang、Rui Zhang、Cai-Xia Song、Rong-Cui Jiang、Xing-Fen Liu、Guang-Wei Zhang、Qu-Li Fan、Lian-Hui Wang、Wei Huang

  DOI：10.1016/j.polymer.2014.12.068

  日期：2015.2

  Two novel water-soluble hyperbranched poly(p-phenyleneethynylene)s (HBP1' and HBP2') bearing different contents of oligo(ethylene oxide) (OEO) side chains with ammonium end groups were synthesized by the facile "A(2) + B-2 (or A(2)') + C-3" protocol based on Sonogashira polymerization. Their linear analog (LP2') was also synthesized for comparative investigation. The optical properties of the neutral precursory polymers in THF and final cationic conjugated polyelectrolytes (CCPs) in aqueous solution were studied. Compared with LP2', HBP1' exhibited increased water solubility and fluorescence quantum yield despite its lower charge density, and HBP2', with the similar charge density as LP2', showed the best water solubility and the highest fluorescence quantum yield among the three CCPs. This indicated that the introduction of hyperbranched structure into conjugated polyelectrolytes was an efficient way to improve water solubility and fluorescence quantum yield because intermolecular aggregation was remarkably prevented. The interactions among the three CCPs and double-stranded DNA (dsDNA) were studied using ethidium bromide (EB) as the fluorescent probe. The electrostatic bindings of the three CCPs with dsDNA/EB complex resulted in displacement of EB from dsDNA to the solution accompanied by the quenching of EB fluorescence. Both HBP1' and HBP2' bound to dsDNA more efficiently than LP2', and HBP2' formed the most stable complex with dsDNA, suggesting that dsDNA might enter the cavities of single-molecular globular architectures of these hyperbranched conjugated polyelectrolytes and induced additional host-guest spatial interactions. Hence, HBP1' and HBP2' may be proved very useful in gene delivery or DNA biosensor applications. (C) 2015 Elsevier Ltd. All rights reserved.
• Design of Cationic Conjugated Polyelectrolytes for DNA Concentration Determination
  作者：Chunyan Chi、Alexander Mikhailovsky、Guillermo C. Bazan

  DOI：10.1021/ja072471s

  日期：2007.9.1

  Cationic conjugated polyelectrolytes poly110 and poly120 were designed, synthesized, and characterized with the anticipation of function in the determination of double-stranded DNA concentration [dsDNA]. Their structures contain a pi-delocalized optically active backbone composed of phenylene-fluorene segments copolymerized with 2,1,3-benzothiadiazole (BT) units and charged pendant groups that allow

  阳离子共轭聚电解质 poly110 和 poly120 被设计、合成和表征，具有测定双链 DNA 浓度 [dsDNA] 的预期功能。它们的结构包含一个由亚苯基-芴链段与 2,1,3-苯并噻二唑 (BT) 单元共聚的 pi 离域光学活性主链和带电的侧基，在水中具有极好的溶解性。poly1x 中的下标是指链中 BT 单元的摩尔百分比。将 dsDNA 添加到 poly110 或 poly120 会导致发射颜色从蓝色变为绿色。可以处理这些光谱变化以获得参数 delta，该参数可用于生成指示 [dsDNA] 的校准曲线。光致发光光谱分析表明，dsDNA 添加导致从蓝色发射段到 BT 位点的更有效的 FRET、BT 发射量子产率的增加和亚苯基-芴段的部分猝灭。还进行了研究以最大化 [dsDNA] 测定的范围。我们发现，通过结合来自两个不同初始浓度 poly110 的响应，可以生成响应超过 7 个数量级的