4,5-Bis(benzimidazol-1-ylmethyl)acridine | 1219605-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4,5-Bis(benzimidazol-1-ylmethyl)acridine
• 英文别名: 4,5-bis(benzimidazol-1-ylmethyl)acridine
• CAS: 1219605-70-5
• 化学式: C₂₉H₂₁N₅
• 分子量: 439.519
• InChiKey: RNWXKUPADAXLRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  48.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-Bis(benzimidazol-1-ylmethyl)acridine 在 ammonium hexafluorophosphate 作用下， 以 水 、 乙腈 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  A bifunctional acridine-based fluorescent sensor: ratiometric sensing of H2PO4− and obvious fluorescence quenching towards HSO4− through a synergistic binding effect of benzimidazolium and urea moieties

  摘要：

  Three tweezer-like fluorescent sensors 1-3 based on acridine fluorophore were designed and synthesized. Anion binding properties of sensors 1-3 were studied by fluorescence, UV-vis, H-1 NMR, and FIRMS. Results showed that the sensor 1, which bears both benzimidazolium and urea groups as binding sites exhibited better anion sensing performance compared with sensors 2 and 3 containing only one kind of binding sites. Especially, it could be used as a dual-responsive selective fluorescent sensor for both H2PO4- and HSO4- via fluorescent bathochromic-shift and fluorescence quenching, respectively. The unique selectivity of sensor 1 towards H2PO4- and HSO4- could be attributed to the synergistic binding effect of benzimidazolium and urea moieties. In addition, the additional hydrogen bond between -OH in H2PO4-/HSO4- and the N on acridine of sensor 1 also played an important role in improving its anion binding affinities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.083
• 作为产物：
  描述：

  吖啶 在 硫酸 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 生成 4,5-Bis(benzimidazol-1-ylmethyl)acridine
  参考文献：
  名称：

  A bifunctional acridine-based fluorescent sensor: ratiometric sensing of H2PO4− and obvious fluorescence quenching towards HSO4− through a synergistic binding effect of benzimidazolium and urea moieties

  摘要：

  Three tweezer-like fluorescent sensors 1-3 based on acridine fluorophore were designed and synthesized. Anion binding properties of sensors 1-3 were studied by fluorescence, UV-vis, H-1 NMR, and FIRMS. Results showed that the sensor 1, which bears both benzimidazolium and urea groups as binding sites exhibited better anion sensing performance compared with sensors 2 and 3 containing only one kind of binding sites. Especially, it could be used as a dual-responsive selective fluorescent sensor for both H2PO4- and HSO4- via fluorescent bathochromic-shift and fluorescence quenching, respectively. The unique selectivity of sensor 1 towards H2PO4- and HSO4- could be attributed to the synergistic binding effect of benzimidazolium and urea moieties. In addition, the additional hydrogen bond between -OH in H2PO4-/HSO4- and the N on acridine of sensor 1 also played an important role in improving its anion binding affinities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.083

文献信息

• Synthesis of Dicationic Acridinophane: Optical and Electrochemical Studies
  作者：Perumal Rajakumar、Sebastian Raja

  DOI：10.1055/s-0029-1218582

  日期：2010.2

  The synthesis of some novel dicationic acridinophanes has been achieved via an N-alkylation route using benzimidazole, imidazole and benzotriazole as building units. UV-Visible studies revealed the absence of ground-state charge-transfer interactions between the acridine and imidazolium moieties. Electrochemical studies showed that the imidazolium and acridine units modify the characteristic redox

  通过使用苯并咪唑，咪唑和苯并三唑作为构建单元的N-烷基化途径，已经实现了一些新的双胍基a啶酮的合成。紫外可见研究表明a啶和咪唑鎓部分之间不存在基态电荷转移相互作用。电化学研究表明，咪唑鎓和a啶单元改变了双胍基d啶的特征氧化还原特性。 阳离子-阳离子-环烷-cr啶-大环-受体
• A bifunctional acridine-based fluorescent sensor: ratiometric sensing of <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" altimg="si1.gif" overflow="scroll"><mml:mrow><mml:msup><mml:mrow><mml:msub><mml:mtext>H</mml:mtext><mml:mn>2</mml:mn></mml:msub><mml:msub><mml:mrow><mml:mtext>PO</mml:mtext></mml:mrow><mml:mn>4</mml:mn></mml:msub></mml:mrow><mml:mo>−</mml:mo></mml:msup></mml:mrow></mml:math> and obvious fluorescence quenching towards <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" altimg="si2.gif" overflow="scroll"><mml:mrow><mml:msup><mml:mrow><mml:msub><mml:mrow><mml:mtext>HSO</mml:mtext></mml:mrow><mml:mn>4</mml:mn></mml:msub></mml:mrow><mml:mo>−</mml:mo></mml:msup></mml:mrow></mml:math> through a synergistic binding effect of benzimidazolium and urea moieties
  作者：Dawei Zhang、Xiaozhi Jiang、Zhiyun Dong、Haiqiang Yang、Alexandre Martinez、Guohua Gao

  DOI：10.1016/j.tet.2013.09.083

  日期：2013.12

  Three tweezer-like fluorescent sensors 1-3 based on acridine fluorophore were designed and synthesized. Anion binding properties of sensors 1-3 were studied by fluorescence, UV-vis, H-1 NMR, and FIRMS. Results showed that the sensor 1, which bears both benzimidazolium and urea groups as binding sites exhibited better anion sensing performance compared with sensors 2 and 3 containing only one kind of binding sites. Especially, it could be used as a dual-responsive selective fluorescent sensor for both H2PO4- and HSO4- via fluorescent bathochromic-shift and fluorescence quenching, respectively. The unique selectivity of sensor 1 towards H2PO4- and HSO4- could be attributed to the synergistic binding effect of benzimidazolium and urea moieties. In addition, the additional hydrogen bond between -OH in H2PO4-/HSO4- and the N on acridine of sensor 1 also played an important role in improving its anion binding affinities. (C) 2013 Elsevier Ltd. All rights reserved.