2,7-di(prop-2-ynyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone | 159638-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,7-di(prop-2-ynyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
• 英文别名: N,Nʼ-bis(prop-2-ynyl)-1,4,5,8-naphthalenetetracarboxylic diimide；bis-N,N'-(prop-2-ynyl)-1,4,5,8-naphthalene-tetracarboxylic diimide；N,N'-bispropargylnaphthalene-1,4,5,8-tetracarboxylic acid diimide；bis-N,N'-(prop-2-ynyl)-1,4,5,8-naphthalenetetracarboxylic diimide；6,13-Bis(prop-2-ynyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 159638-51-4
• 化学式: C₂₀H₁₀N₂O₄
• 分子量: 342.31
• InChiKey: HALKUNDEFRDXKG-UHFFFAOYSA-N

物化性质

• 熔点：
  275-280 °C
• 沸点：
  581.2±45.0 °C(Predicted)
• 密度：
  1.517±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-di(prop-2-ynyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone 、 2,8,11,14,25,28,31,37-Octaoxatetracyclo[36.2.2.015,20.019,24]dotetraconta-1(41),15,17,19,21,23,38(42),39-octaene-7,32-dione 在 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以62%的产率得到
  参考文献：
  名称：

  Unusual Solid-State Behavior in a Neutral [2]Catenane Bearing a Hydrolyzable Component

  摘要：

  A template-directed strategy to forming a bis(diimide) macrocycle through an intermediate asymmetric [2]catenane is reported. Saponification of the ester linkages within the crown ether component is much slower in the mechanically interlocked structure when compared to the free crown. The predominance of a single translational isomer leads to a dimeric structure, resulting in the generation of infinite channels within the crystal lattice.

  DOI：

  10.1021/ol036116s
• 作为产物：
  描述：

  1,4,5,8-萘四甲酸酐 、 炔丙胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以65%的产率得到2,7-di(prop-2-ynyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
  参考文献：
  名称：

  用于调节金属离子超分子相互作用的萘二亚胺环烷的合成

  摘要：

  合成了一种新的含有三唑单元的萘二亚胺环烷的超分子物质，并在二氯甲烷 (DCM) 中研究了其对金属离子的荧光响应。NDI 的荧光发射被分子内电子转移淬灭，而在 Mg2+、Ba2+、Hg2+、Ca2+、Zn2+ 和 Pb2+ 存在的情况下，观察到萘二亚胺的二聚体发射的出现。

  DOI：

  10.1002/ejoc.201200169

文献信息

• Neutral [2]catenanes from oxidative coupling of π-stacked components
  作者：Darren G. Hamilton、Jeremy K. M. Sanders、John E. Davies、William Clegg、Simon J. Teat

  DOI：10.1039/a701048f

  日期：——

  Oxidative dimerisation of bis-acetylenic precursors in the presence of a dinaphtho-crown ether affords neutral [2]catenanes in good yields; the interaction of the complementary donor–acceptor π-systems ensures assembly in a geometry favouring catenane formation.

  在二萘冠醚存在下，双炔烃前体的氧化二聚反应可生成中性[2]链烷，且收率较高；互补供体-受体Β-系统的相互作用可确保在有利于链烷形成的几何结构中进行组装。
• Toward Multistation Rotaxanes Using Metalloporphyrin Coordination Templating
  作者：Kathleen M. Mullen、Maxwell J. Gunter

  DOI：10.1021/jo800276w

  日期：2008.5.1

  This paper describes some approaches toward the templated synthesis of rotaxanes incorporating strapped metalloporphyrin moieties as the shuttle unit, with the thread component containing both a neutral diimide “station” and a functionalized pyridine moiety, the latter acting not only as a template but also as a second binding motif. In the first instance, the use of appropriately 3,5-difunctionalized

  本文介绍了一些方法的轮转烷的模板化合成方法，该方法结合了捆绑的金属卟啉部分作为穿梭单元，其中的线组分既包含中性二酰亚胺“工位”，又包含官能化的吡啶部分，后者不仅充当模板，而且还充当第二结合基序。在第一种情况下，在塞子方法中使用适当的3,5-双官能化吡啶酯和萘喹啉-封端的氯化铑（III）卟啉仅产生未连接的组分：带的柔韧性为潜在的螺纹单元留有足够的空间可以与卟啉绑在带子的同一面上，而不会通过带子互锁。涉及叠氮化物和炔烃之间的1,3-偶极环加成反应（“点击”反应）的替代策略，在轮烷的线组分中产生三唑连接基更为成功。具有多功能（三唑和萘二酰亚胺）螺纹单元的卟啉（锌，游离碱和铑（III）衍生物）和冠醚轮烷均已成功生产。研究了通过使用刺激剂（例如酸，溶剂和竞争性配体）进行分子运动的潜力，但取得的成功有限。相同的环加成方法已扩展到吡啶类化合物在Rh（III）束缚的卟啉中的丝成分的吡啶模板类似物，但是同样
• Neutral π-associated porphyrin [2]catenanes
  作者：Maxwell J. Gunter、Sandra M. Farquhar

  DOI：10.1039/b307383a

  日期：——

  A series of neutral porphyrin-containing catenanes has been synthesised, consisting of a zinc porphyrin strapped by a polyethylene glycol chain containing four or six ethylenoxy-units and incorporating a central naphthoquinol unit, interlinked with a naphthalene diimide macrocycle. The napthalene diimide precursor units exhibit only weak binding with the strapped porphyrins (Ka between 8 and 0.02 M−1), but good yields of the catenanes were obtained by Glaser coupling of the alkynyl napthalene diimide precursors in the presence of the porphyrins. Structures and solution conformations were determined by mass spectral and detailed 1H NMR studies. For the longer strapped porphyrins, the diimide macrocycle rotates around the central naphthoquinol unit at 420–450 times per second, while rotation is virtually prevented in the tighter strapped derivatives. A second dynamic process occurring in both sets of catenanes and described as ‘yawing’ leads to inequivalence in the naphthalene moieties. UV-Visible spectra indicate charge transfer interactions and electronic communication between the two components of the catenane.

  一系列中性含卟啉的链烷已经合成，由锌卟啉和含有四个或六个乙氧基单元的聚乙二醇链组成，并包含一个中心萘醌单元，与萘二酰亚胺大环相互连接。萘二酰亚胺前体单元与束缚卟啉的结合力较弱（Ka在8和0.02 M之间），但在卟啉存在的情况下，通过炔基萘二酰亚胺前体的格拉瑟偶联，获得了良好的链烷产量。通过质谱和详细的1H NMR研究确定了结构和溶液构象。对于较长的束缚卟啉，二酰亚胺大环以每秒420-450次的频率绕中心萘醌单元旋转，而在更紧密的束缚衍生物中，旋转实际上被阻止了。在两组链烷中发生的第二个动态过程被称为“偏航”，导致萘部分的不等价。紫外可见光谱表明链烷的两个成分之间存在电荷转移相互作用和电子通信。
• Synthesis, Structure and Photophysics of Neutral π-Associated [2]Catenanes
  作者：Darren G. Hamilton、John E. Davies、Luca Prodi、Jeremy K. M. Sanders

  DOI：10.1002/(sici)1521-3765(19980416)4:4<608::aid-chem608>3.0.co;2-c

  日期：1998.4.16

  The supramolecular utility of a neutral re-stacking system of aromatic donors and accepters is illustrated with the syntheses of three neutral [2]catenanes. These templated syntheses are based on the oxidative dimerisation of electron-deficient aromatic diimide derivatives, equipped with terminal acetylene functions, in the presence of a preformed crown macrocycle containing complementary electron-rich aromatic diethers. X-ray crystallographic study of one of the catenanes and a precatenane crown/diimide inclusion complex reveals the ordered donor-acceptor stacking responsible for templating the catenane syntheses and subsequently organising the packing of the interlocked molecules in the solid state. NMR investigation of the catenanes reveals a dominant dynamic process at room temperature involving the sweeping of the crown macrocycle around the periphery of the interlocked structures; NOESY exchange spectra reveal a higher-energy process involving the revolution of the crown macrocycle through the centre of the second ring. This combined dynamic picture has been used to support the observed photophysical behaviour. Room-temperature fluorescence of the catenanes is only partially quenched by neighbouring chromophores, implying some mobility in the constituent rings; for one of the catenanes fluorescence quenching data enables an estimate to be made of the ratio of translational isomers present in solution. In contrast, low-temperature (77 K) fluorescence is totally quenched as a consequence of freezing all dynamic movement. Collectively, the results presented in this work lend support to the assertion that the robust, neutral building blocks employed in the catenane syntheses are ideal vehicles for the development of complex [n]catenane syntheses.
• Koshkakaryan, Gayane; Klivansky, Liana M.; Cao, Dennis, Journal of the American Chemical Society, 2009, vol. 131, p. 2078 - 2079
  作者：Koshkakaryan, Gayane、Klivansky, Liana M.、Cao, Dennis、Snauko, Marian、Teat, Simon J.、et al.

  DOI：——

  日期：——