2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl-[1,10]-phenanthroline | 1196061-68-3

• 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: 2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl-[1,10]-phenanthroline
• 英文别名: 2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl[1,10]-phenanthroline；2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl-1,10-phenanthroline；2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl[1,10]phenanthroline
• CAS: 1196061-68-3
• 化学式: C₃₀H₂₄N₂O₄
• 分子量: 476.532
• InChiKey: RQMFMDABJOWRIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.7
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl-[1,10]-phenanthroline 、 3-(2,5-dibutoxy-4-iodo-phenylethynyl)-[1,10]-phenanthroline 在 bis-triphenylphosphine-palladium(II) chloride 、 tetra-n-butylammoniumfluoride trihydrate 作用下， 反应 12.0h， 以64%的产率得到3-[2-[2,5-Dibutoxy-4-[2-(1,10-phenanthrolin-3-yl)ethynyl]phenyl]ethynyl]-2,9-bis(2,6-dimethoxyphenyl)-1,10-phenanthroline
  参考文献：
  名称：

  A fully dynamic five-component triangle via self-sorting

  摘要：

  通过自排序，我们成功构建了五元超分子三角结构。通过改变金属离子及其比例，我们挑战了动态三角结构对外部刺激的稳定性。实践证明，五元超分子三角结构的自排序效果优于四元超分子三角结构。

  DOI：

  10.1039/c0cc00191k
• 作为产物：
  描述：

  2,9-bis(2,6-dimethoxyphenyl)-3-(trimethylsilanylethynyl)[1,10]-phenanthroline 在 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以97%的产率得到2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl-[1,10]-phenanthroline
  参考文献：
  名称：

  From 2-Fold Completive to Integrative Self-Sorting: A Five-Component Supramolecular Trapezoid

  摘要：

  The amalgamation of two incomplete self-sorting processes into a process that makes quantitative use of all members of the library is described by 2-fold completive self-sorting. Toward this goal, individual metal-ligand binding scenarios were optimized for high thermodynamic stability and best selectivity, by screening a variety of factors, such as steric and electronic effects, pi-pi interactions, and metal-ion specifics. Using optimized, heteroleptic metal-ligand binding motifs, a library of four different ligands (1, 2, 3, 4) and two different metal ions (Zn2+, Cu+) was set up to assess 2-fold completive self-sorting. Out of 20 different combinations, the self-sorting library ended up with only two metal-ligand complexes in basically quantitative yield. To demonstrate the value of 2-fold completive self-sorting for the formation of nanostructures, the optimized, highly selective binding motifs were implemented into three polyfunctional ligands. Their integrative self-sorting in the presence of Zn2+ and Cu+ led to the clean formation of the supramolecular trapezoid T, a simple but still unknown supramolecular architecture. The dynamic trapezoid T consists of three different ligands with four different donor-acceptor interactions. Its structure was established by H-1 NMR spectroscopy, electrospray ionization mass spectroscopy, and differential pulse voltammetry (DPV) and by exclusion of alternative structures.

  DOI：

  10.1021/ja907185k

文献信息

• Merging strong and weak coordination motifs in the integrative self-sorting of a 5-component trapezoid and scalene triangle
  作者：Manik Lal Saha、Jan W. Bats、Michael Schmittel

  DOI：10.1039/c3ob41258j

  日期：——

  In a dynamic six-component library, the formation of the rather weak HETPYP-I complexation can be enforced by exploiting the orthogonality and high stability of its counterpart in the sorting process, a HETTAP complex. The concept was used in a follow-up integrative self-sorting, enabling the formation of two five-component supramolecular structures: a trapezoid and a scalene triangle.

  在动态六组分库中，可以利用其对应物--HETTAP 复合物--在分选过程中的正交性和高稳定性，形成相当弱的 HETPYP-I 复合物。这一概念被用于后续的整合自分选，从而形成了两种五组分超分子结构：梯形和不规则三角形。
• A six-component metallosupramolecular pentagon via self-sorting
  作者：Manik Lal Saha、Nikita Mittal、Jan W. Bats、Michael Schmittel

  DOI：10.1039/c4cc05465b

  日期：——

  The six-component pentagon P1 with its five dynamic vertices was conceived on the basis of three different orthogonal metal complex units in a 1-fold completive self-sorting of four linear ligands and two metal ions without using directional bonding.

  六元五角形P1具有五个动态顶点，它是在三个不同的正交金属复合单元的基础上，通过1倍竞争自排序的四线性配体和两个金属离子而构思出来的，无需使用定向键合。
• A phenanthroline–terpyridine hybrid as a chameleon-type ligand in a reversible metallosupramolecular rearrangement
  作者：Manik Lal Saha、Kingsuk Mahata、Debabrata Samanta、Venkateshwarlu Kalsani、Jian Fan、Jan W. Bats、Michael Schmittel

  DOI：10.1039/c3dt51351c

  日期：——

  1 was designed as a chameleon-type ligand to satisfy both HETPHEN and HETTAP coordination modes. In the presence of Cu+, 1 exclusively self-assembled to triangle T1, whereas Zn2+ addition produced a 2 : 1 mixture of triangle T2 and square S2. Interconversion between T1 and (T2 + S2) states was triggered by the addition of Zn2+ and reversed by selectively removing Zn2+ with ligand 7.

  菲咯啉–特吡啶杂种1被设计为变色龙型配体，可以同时满足HETPHEN和HETTAP的配位模式。在Cu +的存在下，1仅自我组装成三角形T1，而添加Zn 2+则生成三角形T2和正方形S2的2：1混合物。T1和（T2 + S2）状态之间的相互转化通过添加Zn 2+触发，并通过用配体7选择性去除Zn 2+来逆转。
• From 3-Fold Completive Self-Sorting of a Nine-Component Library to a Seven-Component Scalene Quadrilateral
  作者：Manik Lal Saha、Michael Schmittel

  DOI：10.1021/ja410425k

  日期：2013.11.27

  Three-fold completive self-sorting of a nine-component library with >= 126 possible combinations led to the clean formation of only three heteroleptic metal ligand complexes. Due to the orthogonality of the latter, they were used as corner stones in an integrative self-sorting approach toward a seven-component scalene quadrilateral.
• From an Eight-Component Self-Sorting Algorithm to a Trisheterometallic Scalene Triangle
  作者：Kingsuk Mahata、Manik Lal Saha、Michael Schmittel

  DOI：10.1021/ja108419k

  日期：2010.11.17

  Using motifs from 3-fold completive self-sorting in an eight-component library, we report on the design and fabrication of a fully dynamic trisheterometallic scalene triangle, a demanding supramolecular structure that complements the so far known triangular structures.