1⁹,4,16-trioxa-1(2,10)-anthracena-2(1,2)-benzenacyclohexadecaphane-1⁷,3(1⁹H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1⁹,4,16-trioxa-1(2,10)-anthracena-2(1,2)-benzenacyclohexadecaphane-1⁷,3(1⁹H)-dione
• 英文别名: 2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid undecanoic ester；1^9^,14-dioxa-1(2,10)-anthracena-2(1,2)-benzenacyclotetradecaphane-1^7^,3(5^9^H)-dione；2,17,29-trioxapentacyclo[28.3.1.03,8.09,33.010,15]tetratriaconta-1(33),3,6,8,10,12,14,30(34),31-nonaene-5,16-dione
• 化学式: C₃₁H₃₂O₅
• 分子量: 484.592
• InChiKey: SUKORLKZLZQISQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  36
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  fluorescein free acid 在 硫酸 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 生成 1⁹,4,16-trioxa-1(2,10)-anthracena-2(1,2)-benzenacyclohexadecaphane-1⁷,3(1⁹H)-dione
  参考文献：
  名称：

  Spectroscopic studies of a fluorescent fluoresceinophane formed via a practical synthetic route

  摘要：

  我们开发了一种包含高荧光荧光素的实用大环合成方法。光物理、晶体学和动态核磁共振研究表明，烷基系链迫使荧光素形成受限构象，从而通过减少激发态失活途径提高了荧光量子产率。与线性类似物相比，受约束的大环构象还能增强随温度变化的荧光，而在不同的极性溶剂中，仍会出现从单重态到三重态的多重转变。

  DOI：

  10.1039/b611060f

文献信息

• A fluoresceinophane: 1⁹,4,16-trioxa-1(2,10)-anthracena-2(1,2)-benzenacyclohexadecaphane-1⁷,3(1⁹<i>H</i>)-dione
  作者：Stéphane Dufresne、Sergio Andrés Pérez Guarìn、W. G. Skene

  DOI：10.1107/s0108270107008566

  日期：2007.6.15

  A novel macrocycle containing fluorescein, the highly fluorescent title compound, C31H32O5, has a xanthene core and a benzyl unit that are planar. The latter is rotated by 72.99 (3)degrees from the xanthene mean plane. The C-11 alkyl tether and the xanthene group adopt a cage-like structure and the xanthene adopts a quinoid-type configuration. The compound crystallizes as a racemic mixture with one molecule of each isomer per unit cell. Even though the planes described by the xanthene and the benzene rings of different molecules are separated by 3.341 (4) and 3.73 (1) angstrom, respectively, there is insufficient overlap between the aryl units to promote pi-stacking.
• Spectroscopic studies of a fluorescent fluoresceinophane formed via a practical synthetic route
  作者：Sergio Andrés Peréz Guarìn、Derek Tsang、W. G. Skene

  DOI：10.1039/b611060f

  日期：——

  A practical macrocycle synthesis incorporating a highly fluorescent fluorescein was developed. Photophysical, crystallographic and dynamic-NMR studies showed the alkyl tether forces a constrained conformation of the fluoresceinophane, which enhances the fluorescence quantum yields by reducing the excited-state deactivation pathways. Enhanced temperature-dependent fluorescence relative to its linear analogue was also found as a result of the constrained macrocycle conformation, while a manifold shift from the singlet to the triplet state still occurred in different polar solvents.

  我们开发了一种包含高荧光荧光素的实用大环合成方法。光物理、晶体学和动态核磁共振研究表明，烷基系链迫使荧光素形成受限构象，从而通过减少激发态失活途径提高了荧光量子产率。与线性类似物相比，受约束的大环构象还能增强随温度变化的荧光，而在不同的极性溶剂中，仍会出现从单重态到三重态的多重转变。