2,3:4,5-bis(1,2-naphtho)-1,6,9,12,15,18,21-heptaoxacyclotricosa-2,4-diene | 41024-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3:4,5-bis(1,2-naphtho)-1,6,9,12,15,18,21-heptaoxacyclotricosa-2,4-diene
• 英文别名: 2,2'-Binaphtho-23-krone-7；12,15,18,21,24,27,30-Heptaoxapentacyclo[29.8.0.02,11.03,8.034,39]nonatriaconta-1(31),2(11),3,5,7,9,32,34,36,38-decaene
• CAS: 41024-79-7；128228-66-0；128228-67-1
• 化学式: C₃₂H₃₆O₇
• 分子量: 532.634
• InChiKey: RJGRCZXSRDCNCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-[2-(2-iodoethoxy)ethoxy]ethanol 在 氢氧化钾 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙二醇 、 丙酮 为溶剂， 反应 194.0h， 生成 2,3:4,5-bis(1,2-naphtho)-1,6,9,12,15,18,21-heptaoxacyclotricosa-2,4-diene
  参考文献：
  名称：

  A Molecular-Level Plug/Socket System: Electronic Energy Transfer from a Binaphthyl Unit Incorporated into a Crown Ether to an Anthracenyl Unit Linked to an Ammonium Ion

  摘要：

  The reversible acid/base- (hydrogen-bonding-) controlled association between racemic crown ethers incorporating a binaphthyl unit (the socket) and wirelike compounds bearing an anthracenyl unit (the plug) is described. The compounds used were the (+/-)binaphthocrown ethers BN20C6, BN23C7, and BN26C8, the amines 9-methyl(aminomethyl)anthracene (AM) and 9-methyl(aminobenzyl)anthracene (AB), and their hexafluorophosphate salts AMH(+)PF(6)(-) and ABH(+)PF(6)(-). The experiments were carried out in CH,CI, solution. Fluorescence data, (1)H NMR spectra, and molecular modeling all point to the formation of stable, pseudorotaxane-type H-bonded adducts of BN23C7 with AMH(+) and of BN26C8 with AMH+ and ABH(+). These systems can be considered as molecular-level plug/socket devices since they are characterized by i) reversible, acid/base-controlled plug in/plug out behavior and ii) photoinduced flow of electronic energy from the binaphthyl to the anthracenyl unit in the plug in state. The above concepts can be easily extended to systems in which a) the plug in/plug out function is stereoselective and b) light excitation induces an electron flow instead of a flow of electronic energy.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<984::aid-chem984>3.0.co;2-t

文献信息

• Czech, B.; Czech, A.; Bartsch, R. A., Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 341 - 343
  作者：Czech, B.、Czech, A.、Bartsch, R. A.

  DOI：——

  日期：——
• CZECH, B.;CZECH, A.;BARTSCH, R. A., J. HETEROCYCL. CHEM., 1984, 21, N 2, 341-343
  作者：CZECH, B.、CZECH, A.、BARTSCH, R. A.

  DOI：——

  日期：——
• A Molecular-Level Plug/Socket System: Electronic Energy Transfer from a Binaphthyl Unit Incorporated into a Crown Ether to an Anthracenyl Unit Linked to an Ammonium Ion
  作者：Eléna Ishow、Alberto Credi、Vincenzo Balzani、Francesco Spadola、Luigi Mandolini

  DOI：10.1002/(sici)1521-3765(19990301)5:3<984::aid-chem984>3.0.co;2-t

  日期：1999.3.1

  The reversible acid/base- (hydrogen-bonding-) controlled association between racemic crown ethers incorporating a binaphthyl unit (the socket) and wirelike compounds bearing an anthracenyl unit (the plug) is described. The compounds used were the (+/-)binaphthocrown ethers BN20C6, BN23C7, and BN26C8, the amines 9-methyl(aminomethyl)anthracene (AM) and 9-methyl(aminobenzyl)anthracene (AB), and their hexafluorophosphate salts AMH(+)PF(6)(-) and ABH(+)PF(6)(-). The experiments were carried out in CH,CI, solution. Fluorescence data, (1)H NMR spectra, and molecular modeling all point to the formation of stable, pseudorotaxane-type H-bonded adducts of BN23C7 with AMH(+) and of BN26C8 with AMH+ and ABH(+). These systems can be considered as molecular-level plug/socket devices since they are characterized by i) reversible, acid/base-controlled plug in/plug out behavior and ii) photoinduced flow of electronic energy from the binaphthyl to the anthracenyl unit in the plug in state. The above concepts can be easily extended to systems in which a) the plug in/plug out function is stereoselective and b) light excitation induces an electron flow instead of a flow of electronic energy.