4,5-bis(4,7,10-trioxaundecane-1-sulfonyl)phthalonitrile | 314263-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5-bis(4,7,10-trioxaundecane-1-sulfonyl)phthalonitrile
• 英文别名: 4,5-Bis[2-[2-(2-methoxyethoxy)ethoxy]ethylsulfanyl]benzene-1,2-dicarbonitrile；4,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethylsulfanyl]benzene-1,2-dicarbonitrile
• CAS: 314263-26-8
• 化学式: C₂₂H₃₂N₂O₆S₂
• 分子量: 484.638
• InChiKey: HMUVHBPYPXEQKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  32
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,5-bis(4,7,10-trioxaundecane-1-sulfonyl)phthalonitrile 在 N,N-二甲基乙醇胺 作用下， 反应 24.0h， 以22%的产率得到6,7,15,16,24,25,33,34-Octakis[2-[2-(2-methoxyethoxy)ethoxy]ethylsulfanyl]-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13,15,17,19(39),20,22,24,26,28(38),30(37),31,33,35-nonadecaene
  参考文献：
  名称：

  Synthesis and Characterization of Novel Tetra- and Octa-Triethyleneoxysulfanyl Substituted Phthalocyanines Forming Lyotropic Mesophases

  摘要：

  Metal-free phthalocyanines and nickel phthalocyanines carrying four or eight oligo(ethyleneoxy)thia groups on peripheral positions have been synthesized from new phthalonitrile derivatives. These phthalocyanine derivatives were characterized both thermotropic and lyotropic mesophases by DSC and X-ray.

  DOI：

  10.1080/10587250008024800
• 作为产物：
  描述：

  三甘醇单甲醚 在 三溴化磷 、 potassium carbonate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 49.0h， 生成 4,5-bis(4,7,10-trioxaundecane-1-sulfonyl)phthalonitrile
  参考文献：
  名称：

  Synthesis and Characterization of Novel Tetra- and Octa-Triethyleneoxysulfanyl Substituted Phthalocyanines Forming Lyotropic Mesophases

  摘要：

  Metal-free phthalocyanines and nickel phthalocyanines carrying four or eight oligo(ethyleneoxy)thia groups on peripheral positions have been synthesized from new phthalonitrile derivatives. These phthalocyanine derivatives were characterized both thermotropic and lyotropic mesophases by DSC and X-ray.

  DOI：

  10.1080/10587250008024800

文献信息

• Distribution of single-walled carbon nanotubes in pyrene containing liquid crystalline asymmetric zinc phthalocyanine matrix
  作者：Sinem Tuncel、Esra Nur Kaya、Mahmut Durmuş、Tamara Basova、Ayşe Gül Gürek、Vefa Ahsen、Hikmat Banimuslem、Aseel Hassan

  DOI：10.1039/c3dt52736k

  日期：——

  A novel pyrene containing asymmetric Zn(II) phthalocyanine (AB3 type) was synthesized and characterized by various spectroscopic techniques as well as elemental analysis. A symmetric polyoxyethylene substituted Zn(II) phthalocyanine (B4 type) derivative was also prepared in order to compare the properties and determine the effect of the pyrene group on the phthalocyanine molecule. Composites of synthesized zinc(II) phthalocyanine–single wall carbon nanotubes (ZnPc–SWCNTs) containing 1 and 2 wt% carbon nanotubes were prepared by mixing these two components in dichloromethane followed by removal of the solvent and drying under vacuum. The liquid crystalline properties of the pure compounds and their composites were investigated in comparison with symmetric polyoxyethylene substituted Zn(II) phthalocyanine (B4 type) by using polarized optical microscopy, differential scanning calorimetry and X-ray diffraction analysis. The distribution of the SWCNTs in the ordered matrix of the columnar mesophase of these derivatives was studied by the method of polarized Raman spectroscopy and scanning electron microscopy (SEM). It was shown that the nature of the mesophases was not altered in these composites. The I(V) dependencies for the films deposited onto interdigitated electrodes were measured and it was shown that the lateral conductivity tends to increase with increasing SWCNT concentration.

  合成了一种新型含芘不对称锌（II）酞菁（AB3 型），并通过各种光谱技术和元素分析对其进行了表征。同时还制备了一种对称的聚氧乙烯取代锌（II）酞菁（B4 型）衍生物，以比较其性质并确定芘基对酞菁分子的影响。将合成的锌(II)酞菁-单壁碳纳米管（ZnPc-SWCNTs）在二氯甲烷中混合，然后除去溶剂并在真空中干燥，制备出含有 1 和 2 wt%碳纳米管的复合材料。通过偏振光学显微镜、差示扫描量热法和 X 射线衍射分析，将纯化合物及其复合材料与对称聚氧乙烯取代锌（II）酞菁（B4 型）进行比较，研究了它们的液晶特性。利用偏振拉曼光谱和扫描电子显微镜（SEM）的方法研究了这些衍生物的柱状介相有序基体中 SWCNT 的分布。结果表明，在这些复合材料中，介相的性质没有改变。测量了沉积在交错电极上的薄膜的 I(V) 相关性，结果表明横向电导率随着 SWCNT 浓度的增加而增加。
• Asymmetric zinc phthalocyanines substituted with a single carboxyl and triethyleneoxysulfonyl groups: synthesis, characterization and validation for photodynamic therapy
  作者：Duygu Aydın Tekdaş、Ayşe G. Gürek、Vefa Ahsen

  DOI：10.1142/s1088424614500709

  日期：2014.10

  This work describes modular pathway towards the synthesis of new specific unsymmetrically (AB3) zinc phthalocyanines that contains three polyoxy ethylene and monocarboxylic acid groups as photosensitizers. Their photophysical and photochemical properties are studied. General trends are described for quantum yields of fluorescence, photodegradation and singlet oxygen quantum yields of these compounds. Therefore, these novel phthalocyanines could potentially be good photosensitizers for photodynamic therapy.

  这项工作描述了合成新的特定非对称（AB3）锌酞菁的模块化途径，这些酞菁含有三个聚氧乙烯和单羧酸基团作为光敏剂。研究了它们的光物理和光化学特性。描述了这些化合物的荧光量子产率、光降解量子产率和单线态氧量子产率的总体趋势。因此，这些新型酞菁有可能成为光动力疗法的良好光敏剂。
• Photophysical and photochemical properties of novel peripherally triethyleneoxysulfanyl substituted monomeric and Si–Si bonded dimeric silicon phthalocyanines
  作者：Sebile Işık Büyükekşi、Mahmut Durmuş、Devrim Atilla

  DOI：10.1142/s1088424616501182

  日期：2016.12

  see text]-trioxaundecylsulfanyl groups were synthesized. These novel phthalocyanine derivatives were characterized by general analysis methods such as FT-IR, MALDI-TOF or HRMS, 1H NMR and UV-vis electronic absorption. Their aggregation behaviors were described in dimethyl sulfoxide (DMSO). In addition, the photophysical and photochemical properties of these phthalocyanines were also investigated in

  合成了带有 4[分子式：见正文]、7[分子式：见正文]、10[分子式：见正文]-三氧杂十一烷基硫烷基的单体和 Si-Si 键合二聚硅 (IV) 酞菁。这些新型酞菁衍生物通过一般分析方法如 FT-IR、MALDI-TOF 或 HRMS 进行表征，1H NMR和UV-vis电子吸收。它们的聚集行为在二甲基亚砜 (DMSO) 中进行了描述。此外，还在 DMSO 中研究了这些酞菁的光物理和光化学性质，以确定这些酞菁作为癌症光动力疗法 (PDT) 的光敏剂的潜力。它们的高单线态氧生成证明了它们对 PDT 应用的适用性。这些外围的4[分子式：见正文]、7[分子式：见正文]、10[分子式：见正文]-三氧杂十一烷基硫烷基取代的硅(IV)酞菁由于其有利的单线态氧生成能力而成为有前途的II型光敏剂。此外，还在 DMSO 中研究了 1,4-苯醌对它们的荧光猝灭行为。
• Design of a Gd-DOTA-Phthalocyanine Conjugate Combining MRI Contrast Imaging and Photosensitization Properties as a Potential Molecular Theranostic
  作者：Duygu Aydın Tekdaş、Ruslan Garifullin、Berna Şentürk、Yunus Zorlu、Umut Gundogdu、Ergin Atalar、Ayse B. Tekinay、Alexander A. Chernonosov、Yusuf Yerli、Fabienne Dumoulin、Mustafa O. Guler、Vefa Ahsen、Ayşe Gül Gürek

  DOI：10.1111/php.12332

  日期：2014.11

  AbstractThe design and synthesis of a phthalocyanine – Gd‐DOTA conjugate is presented to open the way to novel molecular theranostics, combining the properties of MRI contrast imaging with photodynamic therapy. The rational design of the conjugate integrates isomeric purity of the phthalocyanine core substitution, suitable biocompatibility with the use of polyoxo water‐solubilizing substituents, and a convergent synthetic strategy ended by the use of click chemistry to graft the Gd‐DOTA moiety to the phthalocyanine. Photophysical and photochemical properties, contrast imaging experiments and preliminary in vitro investigations proved that such a combination is relevant and lead to a new type of potential theranostic agent.
• Mono-amine Functionalized Phthalocyanines: Microwave-Assisted Solid-Phase Synthesis and Bioconjugation Strategies
  作者：S. Sibel Erdem、Irina V. Nesterova、Steven A. Soper、Robert P. Hammer

  DOI：10.1021/jo901424v

  日期：2009.12.18

  Phthalocyanines (Pcs) are excellent candidates for use as fluors for near-infrared (near-IR) fluorescent tagging of biomolecules for a wide variety of bioanalytical applications. Monofunctionalized Pcs, having two different types of peripheral substitutents, one for covalent conjugation of the Pc to biomolecules and others to improve the solubility of the macrocycle, are ideally suited for the desired applications. To date, difficulties faced during the purification of monofunctionalized Pcs limited their usage in various types of applications. Herein are reported a new synthetic method for rapid synthesis of the target Pes and bioconjugation techniques for labeling of the oligonucleotides with the near-IR fluors. A novel synthetic route was developed utilizing a hydrophilic, poly(ethylene glycol) (PEG)-based support with an acid-labile Rink Amide linker. The Pcs were functionalized with an amine group for covalent conjugation purposes and were decorated with short PEG chains, serving as solubilizing groups. Microwave-assisted solid-phase synthetic method was successfully applied to obtain pure asymmetrically substituted monoamine functionalized Pcs in a short period of time. Three different bioconjugation techniques, reductive amination, amidation, and Huisgen cycloaddition, were employed For covalent conjugation of Pcs to oligonucleotides, The described microwave-assisted bioconjugation methods give an opportunity to synthesize and isolate the Pc-oligonucleotide Conjugate in a few hours.