2,3,6,7-tetrabromo-4,8-bis(ocylcarbamoyl)naphthalene-1,5-dicarboxylic acid | 954374-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3,6,7-tetrabromo-4,8-bis(ocylcarbamoyl)naphthalene-1,5-dicarboxylic acid
• 英文别名: 2,3,6,7-tetrabromo-4,8-bis(octylcarbamoyl) naphthalene-1,5-dicarboxylic acid；2,3,6,7-Tetrabromo-4,8-bis(octylcarbamoyl)naphthalene-1,5-dicarboxylic acid
• CAS: 954374-42-6
• 化学式: C₃₀H₃₈Br₄N₂O₆
• 分子量: 842.258
• InChiKey: IOWXPISBBZKAAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,6,7-tetrabromo-4,8-bis(ocylcarbamoyl)naphthalene-1,5-dicarboxylic acid 在 三溴化磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.5h， 生成 25,26-Dibromo-22,29-dioctyl-3,18,22,29-tetrazaoctacyclo[18.10.2.02,19.04,17.05,14.07,12.024,32.027,31]dotriaconta-1,4(17),5(14),7,9,11,15,19,24,26,31-undecaene-6,13,21,23,28,30-hexone
  参考文献：
  名称：

  A near-infrared fluoride sensor based on a substituted naphthalenediimide–anthraquinone conjugate

  摘要：

  The synthesis and characterization of a highly selective fluoride receptor based on a naphthalene diimide substituted with an anthraquinone (NDI-AQ) moiety is described. In CHCl3, the receptor was shown to be highly selective for fluoride (K-a similar to 10(3) M-1) over other anions (AcO-, HSO4-, Br-, Cl-, I-, ClO4-, H2PO4-, and NO3-) with pronounced changes in absorption characteristics, that is, red-shift of the absorption band to 790 nm (NIR). The visual color change, NIR shift in absorption, emission spectroscopy, and electrochemistry thus support an intramolecular charge transfer (ICT) effect upon fluoride binding to the NDI-AQ receptor. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.050
• 作为产物：
  描述：

  1,4,5,8-萘四甲酸酐 在 发烟硫酸 、 硫酸 、 溴 、 溶剂黄146 作用下， 反应 672.5h， 生成 2,3,6,7-tetrabromo-4,8-bis(ocylcarbamoyl)naphthalene-1,5-dicarboxylic acid
  参考文献：
  名称：

  A near-infrared fluoride sensor based on a substituted naphthalenediimide–anthraquinone conjugate

  摘要：

  The synthesis and characterization of a highly selective fluoride receptor based on a naphthalene diimide substituted with an anthraquinone (NDI-AQ) moiety is described. In CHCl3, the receptor was shown to be highly selective for fluoride (K-a similar to 10(3) M-1) over other anions (AcO-, HSO4-, Br-, Cl-, I-, ClO4-, H2PO4-, and NO3-) with pronounced changes in absorption characteristics, that is, red-shift of the absorption band to 790 nm (NIR). The visual color change, NIR shift in absorption, emission spectroscopy, and electrochemistry thus support an intramolecular charge transfer (ICT) effect upon fluoride binding to the NDI-AQ receptor. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.050

文献信息

• First Synthesis of 2,3,6,7-Tetrabromonaphthalene Diimide
  作者：Xike Gao、Wenfeng Qiu、Xiaodi Yang、Yunqi Liu、Ying Wang、Hengjun Zhang、Ting Qi、Ying Liu、Kun Lu、Chunyan Du、Zhigang Shuai、Gui Yu、Daoben Zhu

  DOI：10.1021/ol701539z

  日期：2007.9.1

  N,N'-Bis(n-octyl)-2,3,6,7-tetrabromonaphthalene diimide (TBNDI) was synthesized by a new imidization reaction and characterized by HRMS, H-1 NMR, C-13 NMR, elemental analyses, FT-IR, UV-vis, and single-crystal X-ray analysis. The TBNDIs are the key precursors for the synthesis of core-tetrasubstituted-naphthalene diimides.
• A near-infrared fluoride sensor based on a substituted naphthalenediimide–anthraquinone conjugate
  作者：Sharad R. Bobe、Sidhanath V. Bhosale、Lathe Jones、Avinash L. Puyad、Aaron M. Raynor、Sheshanath V. Bhosale

  DOI：10.1016/j.tetlet.2015.06.050

  日期：2015.8

  The synthesis and characterization of a highly selective fluoride receptor based on a naphthalene diimide substituted with an anthraquinone (NDI-AQ) moiety is described. In CHCl3, the receptor was shown to be highly selective for fluoride (K-a similar to 10(3) M-1) over other anions (AcO-, HSO4-, Br-, Cl-, I-, ClO4-, H2PO4-, and NO3-) with pronounced changes in absorption characteristics, that is, red-shift of the absorption band to 790 nm (NIR). The visual color change, NIR shift in absorption, emission spectroscopy, and electrochemistry thus support an intramolecular charge transfer (ICT) effect upon fluoride binding to the NDI-AQ receptor. (C) 2015 Elsevier Ltd. All rights reserved.