N,N'-bis(1-pyrenylmethyl)pyridine-2,6-dicarboxamide | 628317-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N,N'-bis(1-pyrenylmethyl)pyridine-2,6-dicarboxamide
• 英文别名: N,N'-Bis(2-pyrenemethyl)pyridine-2,6-dicarboxamide；2-N,6-N-bis(pyren-1-ylmethyl)pyridine-2,6-dicarboxamide
• CAS: 628317-56-6
• 化学式: C₄₁H₂₇N₃O₂
• 分子量: 593.684
• InChiKey: MUNQNTGXFAMIIG-UHFFFAOYSA-N

物化性质

• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-三硝基苯 、 N,N'-bis(1-pyrenylmethyl)pyridine-2,6-dicarboxamide 以 氘代氯仿 为溶剂， 生成 2-N,6-N-bis(pyren-1-ylmethyl)pyridine-2,6-dicarboxamide;1,3,5-trinitrobenzene
  参考文献：
  名称：

  Self-Association and Nitroaromatic-Induced Deaggregation of Pyrene Substituted Pyridine Amides

  摘要：

  The self-assembly features of the bis-pyrene methyl amide functionalized pyridine and benzene "tweezers" 1 and 2 were studied in organic solution and in the solid state. These systems were found to display remarkably different self-association features and optical properties, which was rationalized by control experiments using compounds bearing pyrenemethyl esters, alkyl groups, or a single pyrene substituent (3-6). As dilute solutions in chloroform, tweezers 1 displays both pyrene monomer and excimer emission features reflecting intramolecular contacts between the pyrene subunits. At higher concentrations in chloroform, as well as in the solid state, tweezers 1 self-assembles to form a linear supramolecular polymer. In contrast, tweezers 2 does not interact in an intermolecular fashion and photoexcitation produces emission features characteristic of a pyrene monomer. DFT (density functional theory) and TDDFT (time dependent density functional theory) calculations revealed that the lowest vertical transitions are forbidden and that S-1 of 1 is an emissive state. In contrast to 1 and 2, both pyrene-free control systems 5 and 6 were found to form linearly self-assembled supramolecular arrays in the solid state, albeit of differing structure. Upon exposure to trinitrobenzene (TNB), the self-assembled structures formed from 1 undergo deaggregation to form TNB complexes. This change is reflected in both an easily discernible color change and a quenching of the fluorescence emission intensity. Changes in the optical features were also seen in the case of 2. However, notable differences between these two ostensibly similar systems were seen.

  DOI：

  10.1021/ja411672f
• 作为产物：
  描述：

  2,6-氯甲酰吡啶 、 1-芘甲胺 盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到N,N'-bis(1-pyrenylmethyl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  Extreme Complementarity in a Macrocycle−Tweezer Complex

  摘要：

  Interaction of a novel pyrene-based tweezer molecule with a macrocyclic ether-imide-sulfone results in formation of a strongly bound complex (K-a = 24 000 M-1) in which binding results not only from pi-pi stacking interactions involving pyrene units as donors and macrocyclic naphthalene-tetracarboximide and biphenylenedisulfone groups as acceptors but also from N-(HO)-O-... and C-(HO)-O-... hydrogen bonds and from "reverse" pi-stacking of the electron-poor isophthaloyl residue of the tweezer with an electron-rich 3-aminophenoxy residue of the macrocyclic imide.

  DOI：

  10.1021/ol035626j

文献信息

• Conformational Modulation of Sequence Recognition in Synthetic Macromolecules
  作者：Zhixue Zhu、Christine J. Cardin、Yu Gan、Claire A. Murray、Andrew J. P. White、David J. Williams、Howard M. Colquhoun

  DOI：10.1021/ja2067115

  日期：2011.12.7

  The different triplet sequences in high molecular weight aromatic copolyimides comprising pyromellitimide units ("I") flanked by either ether-ketone ("K") or ether-sulfone residues ("S") show different binding strengths for pyrene-based tweezer-molecules. Such molecules bind primarily to the diimide unit through complementary pi-pi-stacking and hydrogen bonding. However, as shown by the magnitudes of H-1 NMR complexation shifts and tweezer-polymer binding constants, the triplet "SIS" binds tweezer-molecules more strongly than "KIS" which in turn binds such molecules more strongly than "KIK". Computational models for tweezer-polymer binding, together with single-crystal X-ray analyses of tweezer-complexes with macrocyclic ether-imides, reveal that the variations in binding strength between the different triplet sequences arise from the different conformational preferences of aromatic rings at diarylketone and diarylsulfone linkages. These preferences determine whether or not chain-folding and secondary pi-pi-stacking occurs between the arms of the tweezer-molecule and the 4,4'-biphenylene units which flank the central diimide residue.
• Extreme Complementarity in a Macrocycle−Tweezer Complex
  作者：Howard M. Colquhoun、Zhixue Zhu、David J. Williams

  DOI：10.1021/ol035626j

  日期：2003.11.1

  Interaction of a novel pyrene-based tweezer molecule with a macrocyclic ether-imide-sulfone results in formation of a strongly bound complex (K-a = 24 000 M-1) in which binding results not only from pi-pi stacking interactions involving pyrene units as donors and macrocyclic naphthalene-tetracarboximide and biphenylenedisulfone groups as acceptors but also from N-(HO)-O-... and C-(HO)-O-... hydrogen bonds and from "reverse" pi-stacking of the electron-poor isophthaloyl residue of the tweezer with an electron-rich 3-aminophenoxy residue of the macrocyclic imide.
• Self-Association and Nitroaromatic-Induced Deaggregation of Pyrene Substituted Pyridine Amides
  作者：Sung Kuk Kim、Jong Min Lim、Tuhin Pradhan、Hyo Sung Jung、Vincent M. Lynch、Jong Seung Kim、Dongho Kim、Jonathan L. Sessler

  DOI：10.1021/ja411672f

  日期：2014.1.8

  The self-assembly features of the bis-pyrene methyl amide functionalized pyridine and benzene "tweezers" 1 and 2 were studied in organic solution and in the solid state. These systems were found to display remarkably different self-association features and optical properties, which was rationalized by control experiments using compounds bearing pyrenemethyl esters, alkyl groups, or a single pyrene substituent (3-6). As dilute solutions in chloroform, tweezers 1 displays both pyrene monomer and excimer emission features reflecting intramolecular contacts between the pyrene subunits. At higher concentrations in chloroform, as well as in the solid state, tweezers 1 self-assembles to form a linear supramolecular polymer. In contrast, tweezers 2 does not interact in an intermolecular fashion and photoexcitation produces emission features characteristic of a pyrene monomer. DFT (density functional theory) and TDDFT (time dependent density functional theory) calculations revealed that the lowest vertical transitions are forbidden and that S-1 of 1 is an emissive state. In contrast to 1 and 2, both pyrene-free control systems 5 and 6 were found to form linearly self-assembled supramolecular arrays in the solid state, albeit of differing structure. Upon exposure to trinitrobenzene (TNB), the self-assembled structures formed from 1 undergo deaggregation to form TNB complexes. This change is reflected in both an easily discernible color change and a quenching of the fluorescence emission intensity. Changes in the optical features were also seen in the case of 2. However, notable differences between these two ostensibly similar systems were seen.