hexa-2-pyridylhexaazatriphenylene | 1239921-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: hexa-2-pyridylhexaazatriphenylene
• 英文别名: 2,3,6,7,10,11-hexa(2-pyridyl)-dipyrazino[2,3-f:2’,3’-h]quinoxaline；2,3,6,7,10,11-hexakis-(2-pyridyl) dipyrazino[2,3-f:2',3'-h]quinoxaline；HPDQ；HPHAT；4,5,10,11,16,17-Hexapyridin-2-yl-3,6,9,12,15,18-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1,3,5,7,9,11,13,15,17-nonaene；4,5,10,11,16,17-hexapyridin-2-yl-3,6,9,12,15,18-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1,3,5,7,9,11,13,15,17-nonaene
• CAS: 1239921-01-7
• 化学式: C₄₂H₂₄N₁₂
• 分子量: 696.733
• InChiKey: AWNBKQGGZYJHKA-UHFFFAOYSA-N

物化性质

• 密度：
  1.387±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  54
• 可旋转键数：
  6
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  155
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  lanthanum(III) nitrate hexahydrate 、 hexa-2-pyridylhexaazatriphenylene 以 二氯甲烷 、 乙腈 为溶剂， 反应 672.0h， 生成 (2,3,6,7,10,11-hexa(2-pyridyl)-dipyrazino[2,3-f:2’,3’-h]quinoxaline)La₃(NO₃)₉(H₂O)₂
  参考文献：
  名称：

  High-performance fluorescence sensing of lanthanum ions (La³⁺) by a polydentate pyridyl-based quinoxaline derivative

  摘要：

  一种多齿吡啶配体，2,3,6,7,10,11-六（2-吡啶基）-二吡嗪[2,3-f:2′,3′-h]喹喔啉（HPDQ），被发现对La3+具有优异的发光选择性，而对许多其他镧系金属离子（Ce3+，Pr3+，Nd3+，Sm3+，Eu3+，Gd3+，Tb3+，Dy3+，Ho3+，Er3+，Tm3+，Yb3+和Lu3+）则不具有发光选择性。

  DOI：

  10.1039/c6dt01161f
• 作为产物：
  描述：

  二(2-吡啶基)乙二酮 、 苯-1,2,3,4,5,6-六胺 以 溶剂黄146 为溶剂， 生成 hexa-2-pyridylhexaazatriphenylene
  参考文献：
  名称：

  Construction of Microbelts through the Coassembly of a Disclike Molecule and Primary Alkyl Ammoniums: A Noncovalent Strategy to Mimic Covalently Bonded π-Core Alkyl Chain Structure

  摘要：

  In this letter, we report the fabrication of microbelts through the coassembly of hexa-2-pyridyl-hexaazatriphenylen (HPHAT), a disklike pi-conjugated molecule, with primary alkyl ammonium triflate. The strategy is first to construct hydrogen-bonded complexes between HPHAT and primary alkyl ammoniums to mimic covalently bonded pi-core alkyl chain structures, and then the complexes self-assemble into microbelts driven by pi-pi stacking in the pi core and van der Waals interactions between the peripheral alkyl chains. The morphology of as-prepared microbelts has been characterized with scanning electron microscopy (SEM), optical microscopy, polarizing microscopy, and transmission electron microscopy (TEM). Spectroscopic and crystallographic investigations were also carried out to reveal the formation mechanism of the microbelts, through which a sequential self-assembly process has been proposed.

  DOI：

  10.1021/la1022104

文献信息

• Valence-induced assembly of CuI–CuII ions into different discrete coordination architectures by a disk-shaped polypyridyl ligand
  作者：Qiang Zhao、Xiu-Ming Liu、Wei-Chao Song、Xian-He Bu

  DOI：10.1039/c2dt00002d

  日期：——

  The valences of metal ions were found to play key roles in controlling the formation and structures of discrete coordination architectures in a copper and disk-shaped hexa-monodentate ligand system. When CuI and CuII ions react with a polydentate ligand HPDQ, a hexanuclear “double-decker” like discrete “LM3M3L” coordination architecture (CuI)6(HPDQ)2(CHCl3)8 (complex 1), and a “LM3L + LM3” composite structure complex (Cu(NO3)2)6(HPDQ)3 (complex 2) are formed, respectively.

  研究发现，金属离子的价态在控制铜和盘形六齿配体系统中离散配位结构的形成和结构中起着关键作用。当 CuI 和 CuII 离子与多齿配体 HPDQ 反应时，会形成六核“双层”，如离散的“LM3M3L”配位结构 (CuI)6(HPDQ)2(CHCl3)8（配合物 1），并且分别形成→LM3L+LM3→复合结构络合物(Cu(NO3)2)6(HPDQ)3(络合物2)。
• Construction and optical properties of infinite Cd and finite Cu molecules stairs
  作者：Qiang Zhao、Wutao Mao、Zhi Shen、Qinghong Wang、Qian Zhou

  DOI：10.1016/j.molstruc.2016.09.048

  日期：2017.2

  and [(pptp)(pta)Cu2Cl] (2) have been synthesized by solvothermal method based on two polypyridyl ligands, 2,3,6,7,10,11-hexakis- (2-pyridyl)dipyrazino[2,3-f:2′,3′-h]quinoxaline) (hpdq), 4′-(4- (3H-pyrrol-3-yl)phenyl)- 2,2′:6′,2″- terpyridine (pptp) and auxiliary ligand p-phthalic acid (pta), respectively. Single crystal x-ray diffraction analyses reveal that complexes 1 and 2 assembled based on distinct

  摘要 基于两个多吡啶基配体 2,3,6, 通过溶剂热法合成了两种配位配合物 [(hpdq)(pta)Cd]n (1) 和 [(pptp)(pta)Cu2Cl] (2), 7,10,11-hexakis-(2-pyridyl)dipyrazino[2,3-f:2',3'-h]quinoxaline) (hpdq), 4'-(4- (3H-pyrrol-3-yl)苯基)- 2,2':6',2"- 三联吡啶 (pptp) 和辅助配体对苯二甲酸 (pta)。单晶 X 射线衍射分析表明，复合物 1 和 2 基于不同的不对称单元组装，该单元包含一个和两个各自的多吡啶基配体，但分别包含一个 Cd(II) 和两个 Cu(I) 离子。其中，1中的不对称单元通过辅助配体pta的链接扩展为一维链，就像以镉离子为节点连接的无限阶梯。而在二至零维四核结构中，通过辅助配体pta的链接，就像有限的四层阶梯，以铜离子为节
• A Highly Selective On/Off Fluorescence Sensor for Cadmium(II)
  作者：Qiang Zhao、Rui-Fang Li、Sheng-Kai Xing、Xiu-Ming Liu、Tong-Liang Hu、Xian-He Bu

  DOI：10.1021/ic2008182

  日期：2011.10.17

  A polypyridyl ligand, 2,3,6,7,10,11-hexakis(2-pyridyl)dipyrazino[2,3-f:2',3'-h]quinoxaline (HPDQ), was found to have excellent fluorescent selectivity for Cd2+ over many other metal ions (K+, Na+, Ca2+, Mg2+, Mn2+, Fe2+, Ni2+, Co2+, Cu2+, Ag+, Hg2+, Zn2+, and Cr3+) based on the intramolecular charge-transfer mechanism, which makes HPDQ a potential fluorescence sensor or probe for Cd2+. An obvious color change between HPDQ and HPDQ + Cd2+ can be visually observed by the naked eye. The structure of the complex HPDQ-Cd has been characterized by X-ray crystallography. Density functional theory calculation results on the HPDQ and HPDQ-Cd complexes could explain the experimental results.
• Programed self-assembly of microstructures: self-sorting based on size-matched disk-like molecules and remarkable cooperative reinforcement of hydrogen-bonding and donor–acceptor interaction
  作者：Ze-Yun Xiao、Lu Wang、Xin Zhao、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tetlet.2011.05.082

  日期：2011.7

  Self-sorting is commonplace in biological system but seldom applied to orthogonally fabricating micro/nanoscaled objects. In this Letter, this principle has been employed to construct two different microscaled architectures via self-sorted assembly of size-matched disk-like molecules. A remarkable cooperative reinforcement of hydrogen-bonding and donor-acceptor interaction is also observed. (C) 2011 Elsevier Ltd. All rights reserved.
• Construction of Microbelts through the Coassembly of a Disclike Molecule and Primary Alkyl Ammoniums: A Noncovalent Strategy to Mimic Covalently Bonded π-Core Alkyl Chain Structure
  作者：Ze-Yun Xiao、Xin Zhao、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1021/la1022104

  日期：2010.8.17

  In this letter, we report the fabrication of microbelts through the coassembly of hexa-2-pyridyl-hexaazatriphenylen (HPHAT), a disklike pi-conjugated molecule, with primary alkyl ammonium triflate. The strategy is first to construct hydrogen-bonded complexes between HPHAT and primary alkyl ammoniums to mimic covalently bonded pi-core alkyl chain structures, and then the complexes self-assemble into microbelts driven by pi-pi stacking in the pi core and van der Waals interactions between the peripheral alkyl chains. The morphology of as-prepared microbelts has been characterized with scanning electron microscopy (SEM), optical microscopy, polarizing microscopy, and transmission electron microscopy (TEM). Spectroscopic and crystallographic investigations were also carried out to reveal the formation mechanism of the microbelts, through which a sequential self-assembly process has been proposed.