2,7-Dioxa-19,23-diazapentacyclo[23.8.0.08,17.011,16.026,31]tritriaconta-1(25),8(17),9,11,13,15,26,28,30,32-decaene | 1314773-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,7-Dioxa-19,23-diazapentacyclo[23.8.0.08,17.011,16.026,31]tritriaconta-1(25),8(17),9,11,13,15,26,28,30,32-decaene
• 英文别名: 2,7-dioxa-19,23-diazapentacyclo[23.8.0.08,17.011,16.026,31]tritriaconta-1(25),8(17),9,11,13,15,26,28,30,32-decaene
• CAS: 1314773-91-5
• 化学式: C₂₉H₃₂N₂O₂
• 分子量: 440.585
• InChiKey: SXARLSBXUQORDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-Dioxa-19,23-diazapentacyclo[23.8.0.08,17.011,16.026,31]tritriaconta-1(25),8(17),9,11,13,15,26,28,30,32-decaene 、 足球烯 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Supramolecular dyad derived from a buckybowl series of O₂N₂-donor naphthodiaza-crowns coordinated to C₆₀: photophysical, NMR and theoretical studies

  摘要：

  Supramolecular complexation of C-60 with L-1-L-5 were studied in toluene, chloroform and 1,2-dichlorobenzene solvents using UV-vis, fluorescence, H-1, C-13 NMR spectroscopy as well as density functional theory (DFT) calculations. The Job's plot of continuous variation method established 1:1 stoichiometry for L-1-L-5/C-60. Binding constants (K) calculated for L-1-L-5/C-60 were also determined employing UV-vis and fluorescence spectroscopy. Both steady-state and time-resolved fluorescence spectroscopic surveys showed remarkable fluorescence quenching phenomenon for L-1-L-5 in the presence of C-60 which was primarily attributed to involvement of a static process. The observed fluorescence quenching in L-1-L-5 was described in terms of both - and n- interactions of the naphthalene moieties and the nitrogen donor groups on the aza-crown macrocyclic ligands with C-60, respectively. Moreover, DFT calculations using B3LYP/6-31G* basis set confirmed on the aforesaid - interaction of naphthalene groups on the aza-crowns with C-60. The DFT calculations also established significant distributions of charge between C-60 and L-1-L-5 in according to the electronic structure and geometry of L-1-L-5/C-60, very similar to phthalocycnine/C-60 systems.[GRAPHICS].

  DOI：

  10.1080/10610278.2016.1208823
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 乙醇 作用下， 反应 5.0h， 以86%的产率得到2,7-Dioxa-19,23-diazapentacyclo[23.8.0.08,17.011,16.026,31]tritriaconta-1(25),8(17),9,11,13,15,26,28,30,32-decaene
  参考文献：
  名称：

  Efficient synthesis of naphthodiazacrown ethers

  摘要：

  A benign and efficient synthesis of naphthodiazacrown ethers has been described. Reaction of simple dialdehyde precursor with alpha,omega-diamines followed by sodium borohydride reduction leads to 16-27 membered naphthodiazacrown ethers in 80-90% yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.057

文献信息

• Structural relevance of N2O2-donor naphthodiaza-crown macrocyclic ligands to selective fluorescence signaling behavior towards aliphatic tertiary amines
  作者：Bahram Ghanbari、Morteza Zarepour-jevinani

  DOI：10.1016/j.jphotochem.2015.08.010

  日期：2016.1

  primarily due to the involvement of dynamic process. The fluorescence quenching of L1–L5 was described according to the hydrogen bonding of NH groups on the aza-crowns with TEA. A mechanism of proton transfer in excited state in terms of hydrogen bonding of the macrocyclic ligands with amines was also proposed for selective fluorescence quenching of tertiary aliphatic amines by L1–L5.

  合成了一系列N 2 O 2-供体萘二氮杂-冠状大环配体L 1 - L 5，并通过IR，1 H和13 C NMR光谱，质谱以及微分析对其进行了表征。使用乙醇中L 3的紫外可见分光光度法进行的初步观察表明，三乙胺（TEA）在整个光谱中具有明显的蓝移效应。然后，通过L 3检测脂族和芳族胺，接着监测所得加合物与L 1 -L的结合的荧光猝灭。5。在极性乙醇（EtOH）溶剂中的稳态和时间分辨光谱测量均显示，在TEA存在下L 1 – L 5的荧光猝灭现象主要是由于动态过程的参与。L 1 - L 5的荧光猝灭是根据氮杂冠上的NH基与TEA的氢键进行描述的。还提出了在大环配体与胺的氢键作用下，处于激发态的质子转移机理，用于通过L 1 - L 5选择性淬灭脂肪族叔胺。
• Efficient synthesis of naphthodiazacrown ethers
  作者：Pallavi Singh、Rajiv K. Verma、Maya Shankar Singh

  DOI：10.1016/j.tetlet.2011.05.057

  日期：2011.7

  A benign and efficient synthesis of naphthodiazacrown ethers has been described. Reaction of simple dialdehyde precursor with alpha,omega-diamines followed by sodium borohydride reduction leads to 16-27 membered naphthodiazacrown ethers in 80-90% yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Supramolecular dyad derived from a buckybowl series of O₂N₂-donor naphthodiaza-crowns coordinated to C₆₀: photophysical, NMR and theoretical studies
  作者：Bahram Ghanbari、Morteza Zarepour-jevinani

  DOI：10.1080/10610278.2016.1208823

  日期：2017.4.3

  Supramolecular complexation of C-60 with L-1-L-5 were studied in toluene, chloroform and 1,2-dichlorobenzene solvents using UV-vis, fluorescence, H-1, C-13 NMR spectroscopy as well as density functional theory (DFT) calculations. The Job's plot of continuous variation method established 1:1 stoichiometry for L-1-L-5/C-60. Binding constants (K) calculated for L-1-L-5/C-60 were also determined employing UV-vis and fluorescence spectroscopy. Both steady-state and time-resolved fluorescence spectroscopic surveys showed remarkable fluorescence quenching phenomenon for L-1-L-5 in the presence of C-60 which was primarily attributed to involvement of a static process. The observed fluorescence quenching in L-1-L-5 was described in terms of both - and n- interactions of the naphthalene moieties and the nitrogen donor groups on the aza-crown macrocyclic ligands with C-60, respectively. Moreover, DFT calculations using B3LYP/6-31G* basis set confirmed on the aforesaid - interaction of naphthalene groups on the aza-crowns with C-60. The DFT calculations also established significant distributions of charge between C-60 and L-1-L-5 in according to the electronic structure and geometry of L-1-L-5/C-60, very similar to phthalocycnine/C-60 systems.[GRAPHICS].