N-(4-iodophenyl)isocyanuric acid | 327622-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: N-(4-iodophenyl)isocyanuric acid
• 英文别名: 1-(4-Iodophenyl)-1,3,5-triazinane-2,4,6-trione
• CAS: 327622-22-0
• 化学式: C₉H₆IN₃O₃
• 分子量: 331.069
• InChiKey: HERISOBKMDEXSD-UHFFFAOYSA-N

物化性质

• 密度：
  2.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-iodophenyl)isocyanuric acid 在 copper(l) iodide 、 sodium azide 、 sodium ascorbate 、 N,N'-二甲基乙二胺 作用下， 以 乙醇 、 水 为溶剂， 以69 %的产率得到4-azido-phenyl-cyanuric acid
  参考文献：
  名称：

  用于氰尿酸衍生物超分子结合的汉密尔顿-受体-富勒烯寡加合物的区域选择性合成

  摘要：

  这项工作提出了汉密尔顿受体和氰尿酸酯官能化富勒烯寡加合物的区域选择性合成的新概念。基于原位脱保护和点击后官能化方法，将多达十二个汉密尔顿受体/氰尿酸酯部分连接至合适的富勒烯C 60基六加合物前体。通过合成汉密尔顿受体/氰尿酸酯官能化单加合物进一步证明了该方法的多功能性，这是通过直接 Bingel 环丙烷化无法获得的。

  DOI：

  10.1002/chem.202400915
• 作为产物：
  描述：

  对碘苯胺 在 sodium 作用下， 以 乙醇 、 水 为溶剂， 反应 26.0h， 生成 N-(4-iodophenyl)isocyanuric acid
  参考文献：
  名称：

  TiO2 上染料层的非共价后官能化——增强染料敏化太阳能电池注入的工具

  摘要：

  我们报告了新定制的染料层，其一方面用于共价沉积，另一方面用于非共价后功能化 TiO 2纳米粒子薄膜。我们的功能化概念能够将第一层的稳定共价连接与通过汉密尔顿受体-氰尿酸结合基序作为第二层的高度通用和可逆的氢键混合。遵循这个概念，我们逐步集成了第一卟啉层和第二卟啉/BODIPY层。对各个构建块及其相应组合的光物理特性进行了探讨，最有希望的组合在染料敏化太阳能电池（DSSC）中实现。相对于第一卟啉层，添加第二卟啉/BODIPY层将总体DSSC效率提高了高达43%。

  DOI：

  10.1002/chem.202004928

文献信息

• Self-Assembling Depsipeptide Dendrimers and Dendritic Fullerenes with New cis- and trans-Symmetric Hamilton Receptor Functionalized Zn-Porphyrins: Synthesis, Photophysical Properties and Cooperativity Phenomena
  作者：Katja Maurer、Bruno Grimm、Florian Wessendorf、Kristine Hartnagel、Dirk M. Guldi、Andreas Hirsch

  DOI：10.1002/ejoc.201000233

  日期：2010.9

  Two novel supramolecular building blocks, namely cis- and trans-symmetric zinc-porphyrins bearing Hamilton receptors as their focal points (10 and 15), were self-assembled with (i) first-, second- and third-generation depsipeptide cyanurates (21-23); (ii) second-generation dendrofullerene (24), and (iii) cyanuric acid substituted fullerene (20), and probed in a series of photophysical investigations

  两种新型超分子结构单元，即以汉密尔顿受体为焦点的顺式和反式对称锌卟啉（10 和 15），与（i）第一代、第二代和第三代缩肽氰尿酸盐（21 -23); (ii) 第二代树枝状富勒烯 (24) 和 (iii) 氰尿酸取代的富勒烯 (20)，并在一系列光物理研究中进行了探测。重要的是，结合常数 K n 和希尔系数 n H 证实了总体 1:2 化学计量比，表明显着的协同性。作为一般特征，更强的结合从反式对称卟啉异构体演化而来，尽管缩肽配体的空间需求增加意味着结合常数随着每一代而降低。
• The CA.M lattice revisited. Gel formation from a linear bis-isocyanuric acid and 2-amino-4,6-bis-(4- tert -butylphenylamino)-1,3,5-triazine
  作者：M.John Plater、James P Sinclair、Stuart Aiken、Thomas Gelbrich、Michael B Hursthouse

  DOI：10.1016/j.tet.2004.03.059

  日期：2004.7

  Five bis(isocyanuric) acid dimers have been prepared and characterised. The introduction of flexible alkyl chains was necessary to aid solubility. On mixing with N,N-bis(4-tert-butyphenyl)melamine in THF followed by slow evaporation, a viscous gel can form which is interpreted as evidence for the assembly of an infinite 2-D hydrogen bonded network. (C) 2004 Published by Elsevier Ltd.
• Self-assembly of supramolecular oligo-phenylene-ethynylene wires consisting of double Hamilton receptor modified OPE rods and a tetraphenylporphyrin cyanurate
  作者：Florian Wessendorf、Andreas Hirsch

  DOI：10.1016/j.tet.2008.08.054

  日期：2008.12

  The syntheses and characterizations of new oligo-phenylene-ethynylene (OPE) bridged bis-Hamilton receptors 8-9 and their linear H-bonding behaviour with a new cyanuric acid modified tetraphenylporphyrin (TPP) 13 are reported. The resulting rigid complexes consisting of an oligo-phenylene-acetylene wire and two terminating TPPs were characterized by H-1 NMR, UV/vis and fluorescence spectroscopies. The 1:2 compositions of the supramolecular complexes, the association constants K-n and the cooperativity of binding expressed by Scatchard plots and Hill coefficients eta(H) were determined by H-1 NMR titration experiments. The strength of the association constants K-n in CDCl3 at rt was found to be in a range of 10(5) and 10(6) mol(-1) dm(3) for the first complexation and 10(10)-10(12) mol(-1) dm(3) for the second complexation, which is rather strong. (C) 2008 Elsevier Ltd. All rights reserved.
• Ag+ Labeling: A Convenient New Tool for the Characterization of Hydrogen-Bonded Supramolecular Assemblies by MALDI-TOF Mass Spectrometry
  作者：Peter Timmerman、Katrina A. Jolliffe、Mercedes Crego Calama、Jean-Luc Weidmann、Leonard J. Prins、Francesca Cardullo、Bianca H. M. Snellink-Ruël、Roel H. Fokkens、Nico M. M. Nibbering、Seiji Shinkai、David N. Reinhoudt

  DOI：10.1002/1521-3765(20001117)6:22<4104::aid-chem4104>3.0.co;2-q

  日期：2000.11.17

  Herein we describe our results on the characterization of a wide variety of different hydrogen-bonded assemblies by means of a never matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MAL-DI-TOF MS) technique with Ag+ labeling. The labeling technique with Ag+ ions is extremely mild and provides a nondestructive way to generate charged assemblies that can be detected by mass spectrometry, Up to now more than 25 different single (1(3).2(3)), double (3(3).2(6)), and tetrarosettes (4(3).2(12)) have been successfully characterized by the use of this method. The success of the method entirely depends on the presence of a suitable binding site for the Ag+ ion. A variety of functionalities has been identified that provide strong binding sites for Ag+, either acting in a cooperative way (pi -arene and pi -alkene donor functionalities) or individually (cyano and crown ether functionalities). The method works well for assemblies with molecular weights between 2000 and 8000 Da, and most likely far beyond this limit.
• Supramolecular Ruthenium–Alkynyl Multicomponent Architectures: Engineering, Photophysical Properties, and Responsiveness to Nitroaromatics
  作者：Rafik Gatri、Ines Ouerfelli、Mohamed Lofti Efrit、Françoise Serein-Spirau、Jean-Pierre Lère-Porte、Pierre Valvin、Thierry Roisnel、Sébastien Bivaud、Huriye Akdas-Kilig、Jean-Luc Fillaut

  DOI：10.1021/om400811z

  日期：2014.2.10

  A series of H-bonded supramolecular architectures were built from monofunctional M-C = C-R and bifunctional R-C = C-M-C = C-R trans-alkynylbis(1,2-bis(diphenylphosphino)ethane)ruthenium(II) complexes and pi-conjugated modules containing 2,5-dialkoxy-p-phenylene. incorporation on each partner of a cyanuric end and of the complementary Hamilton receptor provided the necessary means to keep the constituents together via strong hydrogen bonding. Characterization of all architectures has been performed on the basis of NMR and photophysical methods. In particular, the formation of a Hamilton receptor/cyanuric acid complex has been exemplified by an X-ray single-crystal structure determination. Both self-assembly and accurate modification of the complementary blocks were ensured in such a way that the resulting materials maintain the responsiveness of the electron-rich 2,5-dialkoxy-p-phenylene spacers toward nitroaromatics.