4′-[(4-[1,10]phenanthrolin-3-ylethynyl)phenyl][2,2':6′,2'']terpyridine | 1196061-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 4′-[(4-[1,10]phenanthrolin-3-ylethynyl)phenyl][2,2':6′,2'']terpyridine
• 英文别名: 3-[2-[4-(2,6-Dipyridin-2-ylpyridin-4-yl)phenyl]ethynyl]-1,10-phenanthroline；3-[2-[4-(2,6-dipyridin-2-ylpyridin-4-yl)phenyl]ethynyl]-1,10-phenanthroline
• CAS: 1196061-65-0
• 化学式: C₃₅H₂₁N₅
• 分子量: 511.585
• InChiKey: WSMCLDJYXKOWAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4′-[(4-[1,10]phenanthrolin-3-ylethynyl)phenyl][2,2':6′,2'']terpyridine 、 zinc trifluoromethanesulfonate 以 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Metal–Ligand Exchange in a Cyclic Array: The Stepwise Advancement of Supramolecular Complexity

  摘要：

  Herein, we demonstrate how the supramolecular complexity (evaluated by the degree of self-sorting M) evolves in a chemical cycle of cascaded metallosupramolecular transformations, using abiological self-assembled entities as input signals. Specifically, the successive addition of the supramolecular self-assembled structures S1 and (T2 + S2) to the starting supramolecular two-component equilateral triangle Ti (M = 1) first induced a fusion into the three-component quadrilateral R1 (M = 6) and then to the five-component scalene triangle T3 (M = 16). Upon the addition of the supra molecular input M1 to T3, a notable self-sorting event occurred, leading to regeneration of the triangle T1 along with formation of the scalene triangle T4 (M = 25). This last step closed the cycle of the supramolecular transformations.

  DOI：

  10.1021/acs.inorgchem.6b02256
• 作为产物：
  描述：

  4'-(4-碘苯基)-2,2':6',2''-三联吡啶 、 3-乙炔基-1,10-菲咯啉 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基氟化铵 作用下， 以83%的产率得到4′-[(4-[1,10]phenanthrolin-3-ylethynyl)phenyl][2,2':6′,2'']terpyridine
  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

• A fully dynamic five-component triangle via self-sorting
  作者：Michael Schmittel、Kingsuk Mahata

  DOI：10.1039/c0cc00191k

  日期：——

  Clean fabrication of a five-component supramolecular triangle was elaborated via self-sorting. The robustness of the dynamic triangle against external stimuli was challenged by varying both the metal ions and their ratios. Self-sorting of five components proved to be superior to that of four components.

  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。
• 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.
• Metal–Ligand Exchange in a Cyclic Array: The Stepwise Advancement of Supramolecular Complexity
  作者：Manik Lal Saha、Michael Schmittel

  DOI：10.1021/acs.inorgchem.6b02256

  日期：2016.12.5

  Herein, we demonstrate how the supramolecular complexity (evaluated by the degree of self-sorting M) evolves in a chemical cycle of cascaded metallosupramolecular transformations, using abiological self-assembled entities as input signals. Specifically, the successive addition of the supramolecular self-assembled structures S1 and (T2 + S2) to the starting supramolecular two-component equilateral triangle Ti (M = 1) first induced a fusion into the three-component quadrilateral R1 (M = 6) and then to the five-component scalene triangle T3 (M = 16). Upon the addition of the supra molecular input M1 to T3, a notable self-sorting event occurred, leading to regeneration of the triangle T1 along with formation of the scalene triangle T4 (M = 25). This last step closed the cycle of the supramolecular transformations.
• From 2-Fold Completive to Integrative Self-Sorting: A Five-Component Supramolecular Trapezoid
  作者：Kingsuk Mahata、Michael Schmittel

  DOI：10.1021/ja907185k

  日期：2009.11.18

  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.