4,5-bis(propylsulfonyl)phthalonitrile | 268536-36-3

• 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(propylsulfonyl)phthalonitrile
• 英文别名: 4,5-di(propylsulfonyl)phthalonitrile；4,5-dipropylsulfonylphthalonitrile；4,5-Bis(propylsulfonyl)benzene-1,2-dicarbonitrile
• CAS: 268536-36-3
• 化学式: C₁₄H₁₆N₂O₄S₂
• 分子量: 340.424
• InChiKey: DLKGMGHENXRLIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-bis(propylsulfonyl)phthalonitrile 在 氨 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以45%的产率得到5,6-di(propylsulfonyl)-1,3-diiminoisoindoline
  参考文献：
  名称：

  液晶中酞菁-[60]富勒烯二元的自组织

  摘要：

  使用其中液晶元将介晶性诱导为非介晶化合物的共混物，使得酞菁-[60]富勒烯（Pc-C 60）二元化合物自组织成液晶成为可能。PC-C 60个成对层1，2，或3，其中两个光活性单元由亚苯基亚乙烯基间隔件放在一起时，已通过Heck反应合成的链接4-乙烯基苯甲醛到monoiodophthalocyanine前体，然后通过甲亚胺叶立德的标准环加成产生从甲酰基Pc衍生物和N-甲基甘氨酸到C 60的双键之一。通过形成不同的混合物的介晶性质和热性质的液晶性酞菁4和成对层1，2，或3使用偏光显微镜（POM），差示扫描量热法（DSC），和X射线衍射（XRD）进行了研究。共混物的DSC图显示从晶态到中间相的清晰过渡，并且从粉末衍射实验获得的测量结构参数与盘状六方柱状（Col h）结构一致。考虑到在Pc-C 60 dyad和酞菁4的分离分子域中的偏析由于柱直径的不匹配和纯二元体缺乏介晶特性而将导致同构现象的发生

  DOI：

  10.1021/jo7022763
• 作为产物：
  描述：

  4,5-二氯邻苯二甲腈 在 双氧水 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 溶剂黄146 为溶剂， 反应 15.0h， 生成 4,5-bis(propylsulfonyl)phthalonitrile
  参考文献：
  名称：

  Synthesis of Novel Push−Pull Unsymmetrically Substituted Alkynyl Phthalocyanines

  摘要：

  Two families of "push-pull" phthalocyanines 1-3 having an unusually strong dipole moment have been prepared. The syntheses of unsymmetrically substituted phthalocyanines 1a,b and 2 bearing one or two electron-withdrawing 4-nitrophenylethynyl moieties, respectively, and six alkoxy substituents were performed by combination of a zinc or nickel templated cyclotetramerization and cross-coupling palladium mediated methodologies. In a similar way, the "push-pull" compounds 3a,b having a reversal substitution pattern, characterized by the presence of one electron-donor 4-(dimethylamino)phenylethynyl unit and six strong acceptor alkylsulfonyl substituents were prepared. The compounds show very large second-order nonlinear optical responses.

  DOI：

  10.1021/jo991843f

文献信息

• First Synthesis of Symmetrical and Unsymmetrical Conjugated Trinuclear Phthalocyanines Covalently Linked by Ethynyl Bridges
  作者：Purificación Vázquez、Tomás Torres、Eva García-Frutos、David Díaz

  DOI：10.1055/s-2006-951547

  日期：——

  unsymmetrical π-electron-conjugated trinuclear phthalocyanines (Pcs) were synthesized with the Pc units connected directly by ethynyl linkages. Symmetrically alkoxy-substituted bridged ethynylphthalocyaninatozinc(II) triad was prepared by direct Sonogashira cross-coupling reaction between suitable diiodo Pc and alkynyl Pc derivatives. Nevertheless, the synthesis of the Pc-based triad having a donor-acceptor

  首次合成了对称和不对称的 π 电子共轭三核酞菁 (Pcs)，其中 Pc 单元通过乙炔键直接连接。对称烷氧基取代的桥接乙炔基酞菁锌 (II) 三元组是通过合适的二碘 Pc 和炔基 Pc 衍生物之间的直接 Sonogashira 交叉偶联反应制备的。然而，具有供体-受体电子特征的基于 Pc 的三联体的合成是通过两种不同的邻苯二甲腈，即 4,5-双（丙基磺酰基）邻苯二甲腈和 4,5- [六(丁氧基)乙炔基酞菁锌(II)]邻苯二甲腈在钴(II)盐的存在下。
• Donor−Acceptor Phthalocyanine Nanoaggregates
  作者：Andrés de la Escosura、M. Victoria Martínez-Díaz、Pall Thordarson、Alan E. Rowan、Roeland J. M. Nolte、Tomás Torres

  DOI：10.1021/ja030038m

  日期：2003.10.1

  A novel donor-acceptor bisphthalocyanine (bis-Pc, 1) in which two different PC units (Zn(II)-Pc and Ni(II)-Pc) are linked via vinylene spacers to the pseudopara positions of a central [2.2]paracyclophane moiety is described. The synthesis of 1 is achieved by two successive Heck reactions of pseudopara-divinyl[2.2]paracyclophane 9 with, sequentially, a zinc(II)- and a nickel(II)-iodophthalocyanine (4 and 5, respectively). The self-assembly ability of 1, which is the result of the complementary donor-acceptor character of its phthalocyanine units, has been assessed by a variety of techniques. It is revealed that 1 forms one-dimensional aggregates of nanometer-sized dimension, whereas equimolar mixtures of the donor and acceptor PC subunits 2 and 3, although strongly interacting, do not give large arrays. The aggregates of 1 represent a novel type of supramolecular polymers based mainly upon donor-acceptor interactions.
• Stabilization of Charge-Separated States in Phthalocyanine−Fullerene Ensembles through Supramolecular Donor−Acceptor Interactions
  作者：Andrés de la Escosura、M. Victoria Martínez-Díaz、Dirk M. Guldi、Tomás Torres

  DOI：10.1021/ja058123c

  日期：2006.3.1

  A novel ZnPC-C-60 dyad (3), in which two photoactive units are brought together by a phenylenevinylene spacer has been synthesized. The synthetic strategy en route toward 3 involves a Heck reaction to attach 4-vinylbenzaldehyde to a monoioclophthalocyanine precursor, followed by standard cycloaddition of azomethine ylides (generated from the formylPc derivative and N-methylglycine) to one of the double bonds of C-60. Electrochemical studies reveal that in 3 the ZnPc is about 39 mV more difficult to oxidize than in the corresponding ZnPc, reference, which points to appreciable electronic communication between ZnPc and C-60 in the ground state. In the excited state, photoexcitation leads to the formation of a charge-separated ZnPC.+-C-60(.-) state, for which a lifetime of 130 ns was determined in THF. Hetero-association between complementary PCs (1 and 2 or 3 and 2), which carry different peripheral functionalities (i.e., either electron-donating alkoxy groups or electron-deficient alkylsulfonyl chains) was assessed by different techniques. They provided evidence for donor-acceptor 1:1 complex formation with a stability constant of ca. 10(5) M-1 in CHCl3. Interestingly, hetero-association of ZnPC-C-60 dyad 3 with an electrondeficient PdPc (2) allowed the construction of supramolecular triads, in which a substantial stabilization of the radical pair is seen relative to that of the covalently linked dyad ZnPC-C-60 (3).
• 10.1021/acs.biomac.3c01382
  作者：Şahin, Zeynel、Önal, Emel、Ali, Lamiaa M. A.、Durand, Denis、Emami, Atefeh、Touré, Marie、İşci, Umit、Gary-Bobo, Magali、Cammas-Marion, Sandrine、Dumoulin, Fabienne

  DOI：10.1021/acs.biomac.3c01382

  日期：——
• Synthesis of Novel Push−Pull Unsymmetrically Substituted Alkynyl Phthalocyanines
  作者：Eva M. Maya、Concepción García、Eva M. García-Frutos、Purificación Vázquez、Tomás Torres

  DOI：10.1021/jo991843f

  日期：2000.5.1

  Two families of "push-pull" phthalocyanines 1-3 having an unusually strong dipole moment have been prepared. The syntheses of unsymmetrically substituted phthalocyanines 1a,b and 2 bearing one or two electron-withdrawing 4-nitrophenylethynyl moieties, respectively, and six alkoxy substituents were performed by combination of a zinc or nickel templated cyclotetramerization and cross-coupling palladium mediated methodologies. In a similar way, the "push-pull" compounds 3a,b having a reversal substitution pattern, characterized by the presence of one electron-donor 4-(dimethylamino)phenylethynyl unit and six strong acceptor alkylsulfonyl substituents were prepared. The compounds show very large second-order nonlinear optical responses.