4,5-diiodophthalimide | 68218-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4,5-diiodophthalimide
• 英文别名: 5,6-diiodo-isoindole-1,3-dione；1H-Isoindole-1,3(2H)-dione, 5,6-diiodo-；5,6-diiodoisoindole-1,3-dione
• CAS: 68218-30-4
• 化学式: C₈H₃I₂NO₂
• 分子量: 398.926
• InChiKey: HCZXEHIZHZGQEB-UHFFFAOYSA-N

物化性质

• 熔点：
  257 °C(Solv: acetic acid (64-19-7))
• 密度：
  2.629±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-diiodophthalimide 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 copper(l) iodide 、 三乙胺 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.62h， 生成 4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile
  参考文献：
  名称：

  Synthesis of 2,3,9,10,16,17,23,24-Octaalkynylphthalocyanines and the Effects of Concentration and Temperature on Their ¹H NMR Spectra

  摘要：

  The syntheses of 3,4- and 4,5-diiodophthalonitriles are described. Coupling of the latter compound with Pd(PPh(3))(2)Cl-2 and 1-octyne, 1-heptyne, 1-hexyne, 1-pentyne, and 3,3-dimethyl-1-butyne gave a series of 4,5-dialkynylphthalonitriles. Hydrogenation of 4,5-bis(1-pentynyl)phthalonitrile and 4,5-bis(3,3-dimethyl-1-butynyl)phthalonitrile gave 4,5-dipentylphthalonitrile and 4,5-bis(3,3-dimethylbutyl)phthalonitriles. Condensation of the dialkynylphthalonitriles with lithium 1-pentoxide in 1-pentanol gave 2,3,9,10,16,17,23,24-octaalkynylphthalocyanines, while intervention of the intermediate dilithium phthalocyanines with zinc acetate gave the related zinc(II) phthalocyanines. H-1 NMR spectroscopy of these octaalkynylphthalocyanines exhibited large chemical shifts (1-2 ppm) of the internal and aromatic protons at concentrations ranging from 10(-2) to 10(-5) M and at temperatures from 27 to 147 degrees C. The effects of aggregation phenomena are discussed. The importance of reporting concentration and temperature values for NMR spectra of phthalocyanines is stressed.

  DOI：

  10.1021/jo9521662
• 作为产物：
  描述：

  邻二甲苯 在 potassium permanganate 、 碘 、 formamide 、 高碘酸 作用下， 以 吡啶 、 2,2,2-三氟乙醇 、 硫酸 、 水 、 溶剂黄146 为溶剂， 反应 216.58h， 生成 4,5-diiodophthalimide
  参考文献：
  名称：

  六硫代-亚酞菁的简便合成，三重态性质和电化学

  摘要：

  鉴于对各种光电器件的高效三重态光敏剂和光敏组件的需求不断增长，我们在此报告六碘代亚酞菁（I 6 SubPcs）的合成和性能。据报道，经过改进的五步合成4,5-二碘代邻苯二甲腈的方法可作为I 6 SubPcs的合成前体。改进的合成仅需进行一次色谱分离即可得到高纯度的目标产物。由于存在六个重碘原子，在I 6 SubPcs中诱导了非常理想的光物理和光化学性质。特别地，单线态氧量子产率（高值Φ Δ测定）为0.83〜0.9。我6个SubPcs研究证明是磷光在77K的2-MeTHF与发射带的最大值（λ P位于）λ = 957和970纳米。激发态-三重态态能量（Ë Ť）被估计为约1.30电子伏特，而三线态寿命（τ Ť）被发现是27.7和30.1微秒。CV / DPV测量表明，这两个I 6 SubPcs均表现出一种不可逆的氧化作用和一种准可逆的还原作用。光谱电化学测量表明，电化学形成的阴离子自由基，即I 6

  DOI：

  10.1002/chem.201803316

文献信息

• Dicyanobenzene and dicyanopyrazine derived X-shaped charge-transfer chromophores: comparative and structure–property relationship study
  作者：L. Dokládalová、F. Bureš、W. Kuznik、I. V. Kityk、A. Wojciechowski、T. Mikysek、N. Almonasy、M. Ramaiyan、Z. Padělková、J. Kulhánek、M. Ludwig

  DOI：10.1039/c4ob00901k

  日期：——

  A series of novel X-shaped push–pull compounds based on benzene-1,2-dicarbonitrile has been designed, synthesized and further investigated by X-ray analysis, electrochemistry, absorption and emission spectra, SHG experiment and quantum-chemical calculations. The obtained data were compared with those for isolobal 5,6-disubstituted pyrazine-2,3-dicarbonitriles. Structure–property relationships were elucidated. The extension, composition and planarization of the π-linker used as well as the electron-withdrawing ability of both dicyano-substituted acceptor units affect the linear and nonlinear properties of the target charge-transfer chromophores most significantly.

  基于苯-1,2-二氰基化合物设计、合成了一系列新型的X形推-拉化合物，并通过X射线分析、电化学、吸收和发射光谱、SHG实验及量子化学计算进行了进一步研究。所获得的数据与等边的5,6-二取代吡嗪-2,3-二氰基化合物的数据进行了比较。阐明了结构-性质关系。所使用的π-连接体的延伸、组成和平面化，以及双氰取代的受体单元的电子吸引能力，对目标电荷转移色谱的线性和非线性性质产生了最显著的影响。
• A Cyclic Porphyrin Trimer as a Receptor for Fullerenes
  作者：Guzmán Gil-Ramírez、Steven D. Karlen、Atsuomi Shundo、Kyriakos Porfyrakis、Yasuhiro Ito、G. Andrew D. Briggs、John J. L. Morton、Harry L. Anderson

  DOI：10.1021/ol101393h

  日期：2010.8.6

  A cyclic porphyrin trimer has been synthesized which has a high affinity for fullerenes. It forms 1:1 complexes with C60 and C70 with association constants of 2 × 106 and 2 × 108 M−1, respectively, in toluene. Its affinities for C86 and [email protected]82 are too strong to measure by fluorescence titration. The solvent dependence of the association constants shows that solvation of both the guest

  已经合成了对富勒烯具有高亲和力的环状卟啉三聚体。它在甲苯中分别与C 60和C 70形成1：1配合物，缔合常数分别为2×10 6和2×10 8 M -1。它对C 86和[电子邮件保护的] 82的亲和力太强，无法通过荧光滴定法进行测量。缔合常数对溶剂的依赖性表明，客体和主体的溶剂化都会影响结合强度。
• Control of the molecular packing of chloroboron(<scp>iii</scp>) and fluoroboron(<scp>iii</scp>) subnaphthalocyanines by designing peripheral substituents
  作者：Akuto Takagi、Tadashi Mizutani

  DOI：10.1039/c7ra11104e

  日期：——

  Chloroboron(III) and fluoroboron(III) hexa(1-alkynyl)- and hexa(2-arylethynyl)subnaphthalocyanines with a large dipole moment were prepared by Sonogashira coupling of hexaiodosubnaphthalocyanines with substituted acetylenes. Introduction of butyl or longer alkyl groups via ethynylene linkages on the periphery resulted in lower melting points and higher solubility in dichloromethane. X-ray diffraction (XRD) patterns

  通过Sonogashira偶联六碘亚萘酞菁与取代的乙炔，制备了具有大偶极矩的氯硼烷（III）和氟硼（III）六（1-炔基）-和六（2-芳基乙炔基）亚萘菁。通过乙炔键在周边引入丁基或更长烷基会导致较低的熔点和较高的二氯甲烷溶解度。流延膜的X射线衍射（XRD）图表明，具有B-F键的六（2-（4-己基苯基）乙炔基）-和六（2-（4-己氧基苯基）乙炔基）亚萘菁被填充在盘状中六方柱状相，晶格常数a = 59–64Å，堆积距离c= 4.7–4.8Å。这些B–F衍生物薄膜的可见光谱中的Q带发生了蓝移，从而支持了堆积柱中H聚集体的形成。偏光光学显微镜显示，这些具有B-F键的亚萘酞菁在180°C时表现出中间相。这些亚萘酞菁在180°C的XRD证实是二维六方相。带有B–Cl键的相应衍生物的X射线衍射表明，它们要么是非晶态的，要么是结晶度较低的。我们建议，由于F的范德华半径比Cl小，因此BF基团中的氟原子可以嵌
• Octakis(dodecyl)phthalocyanines: Influence of Peripheral versus Non-Peripheral Substitution on Synthetic Routes, Spectroscopy and Electrochemical Behaviour
  作者：Glendin Swart、Eleanor Fourie、Jannie C. Swarts

  DOI：10.3390/molecules27051529

  日期：——

  5-bis(dodecyl)phthalonitrile (5), template cyclotetramerization of precursor phthalonitriles in the presence of Zn or Mg, metal insertion into metal-free phthalocyanines, and removal of Mg or Zn from the phthalocyaninato coordination cavity. The more effective synthetic route towards pPc 8 was demetalation of 7. npPc’s were more soluble than pPc’s. The Q-band λmax of npPc’s was red-shifted with ca. 18 nm, compared

  非外围八基取代的酞菁 (npPC's)、MPC(C12H25)8，其中 M = 2H (3) 或 Zn (4)，以及外围八基取代的酞菁 (pPC's)，其中 M = Zn (6)、Mg ( 7) 和 2H (8)，通过 3,6- (2) 或 4,5-双（十二烷基）邻苯二甲腈 (5) 的环四聚、在 Zn 或 Mg 存在下前体邻苯二甲腈的模板环四聚、金属插入到不含金属的酞菁，并从酞菁配位空腔中除去镁或锌。 pPC 8 更有效的合成途径是 7 的脱金属。npPC 比 pPC 更易溶解。 npPC 的 Q 带 λmax 发生红移约。 18 nm，与 pPC 相比。 X 射线光电子能谱 (XPS) 区分了不含金属的酞菁的 N–H、Nmeso 和 Ncore 氮原子。结合能约为。分别为 399.6、398.2 和 397.7 eV。 X 射线光电子能谱 (XPS) 还显示锌酞菁 4 和 6 具有四个等效的
• Vibrational spectra of halophthalonitriles
  作者：Mathew D Halls、Ricardo Aroca、Dmitri S Terekhov、Anna D'Ascanio、Clifford C Leznoff

  DOI：10.1016/s1386-1425(97)00236-9

  日期：1998.2

  The fundamental vibrational modes of a series of six halophthalonitriles have been studied using Raman and infrared spectroscopy. The vibrational assignment of experimental wave numbers obtained from solid samples was aided using quantum chemical computations. Semi-empirical methods and the local SVWN functional were used to obtain vibrational wave numbers and atomic displacement representations of the fundamental molecular vibrations. The study of a series of molecules with similar structure permits the identification of characteristic wave numbers and the effect of the halosubstitution in the molecular structure. (C) 1998 Elsevier Science B.V. All rights reserved.