3'-(1-hydroxyhexane-3-ylthio)phthalonitrile | 1261153-66-5

• 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: 3'-(1-hydroxyhexane-3-ylthio)phthalonitrile
• 英文别名: 3'-(1-hydroxyhexan-3-ylthio)phthalonitrile；3-(1-hydroxyhexan-3-ylthio)phthalonitrile；3-(1-Hydroxyhexan-3-ylthio)phthalonitrile；3-(1-hydroxyhexan-3-ylsulfanyl)benzene-1,2-dicarbonitrile
• CAS: 1261153-66-5
• 化学式: C₁₄H₁₆N₂OS
• 分子量: 260.36
• InChiKey: ZHZSTHZWCOBNLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 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：
  93.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-(1-hydroxyhexane-3-ylthio)phthalonitrile 在 lead(II) acetate trihydrate 作用下， 以 无水二甲氨基乙醇 为溶剂， 反应 5.0h， 以30.65%的产率得到1(4),8(11),15(18),22(25)-tetrakis(1-hydroxyhexan-3-ylthio)phthalocyaninatolead(II)
  参考文献：
  名称：

  Synthesis, H- or J-type aggregations, electrochemistry and in situ spectroelectrochemistry of metal ion sensing lead(II) phthalocyanines

  摘要：

  We report, in this study, peripherally 3- and 4-substituted functionalized ionophore ligands (1-3) and their alpha- and beta-tetra polyalcohol substituted lead(II) phthalocyanines M{Pc[S-CH(C3H7)(C2FH5OH)](4)} (7, 9 and 11) and M{Pc(S-C6H12(OH)](4)) (8. 10 and 12) which are a mixture of different isomers. The complexes have been fully characterized by elemental analysis, FT-IR, H-1 NMR, C-13 NMR, MS (MALDI-TOF) and UV-Vis spectral data. These complexes induced H-type (face-to-face fashion) on-aggregate (edgeto-edge) dimers when titrated with AgNO3 or Na2PdCl4 in a THF-MeOH solution. Cyclic and square wave voltammetry studies showed that the complexes gave three one-electron ligand-based reductions and two one-electron oxidation couples having diffusion controlled mass transfer character. Assignments of these redox couples were confirmed by spectroelectrochemical measurements. The observation of split Q bands, which are characteristic spectral behavior of metal-free phthalocyanines, indicates demetallization of the complexes during the spectroelectrochemical measurement under the applied potentials. The types of the substituents on the ring of the phthalocyanines affect the demetallization process of the complexes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.09.035
• 作为产物：
  描述：

  3-巯基-1-己醇 、 3-硝基邻苯二腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3'-(1-hydroxyhexane-3-ylthio)phthalonitrile
  参考文献：
  名称：

  基于金属诱导的荧光受体的H型聚集，阐明了银离子的选择性。

  摘要：

  在目前的工作中，通过亲核取代反应制备了一种新的取代邻苯二甲腈衍生物，然后通过环四聚合成了具有四个外围1-羟基己-3--3-硫基的高可溶性酞菁锌（ZnPc），并通过FTIR，1 H和13 C进行了表征。NMR光谱学，荧光和紫外可见测量。在具有不同组成的乙醇/水混合溶剂中阐明了ZnPc的光学性质和量子产率。获得了在不存在和存在Ag +离子的情况下ZnPc的pH依赖性荧光和吸收光谱，以阐明便于在预定混合物中稳定形成络合物的最佳pH值。Ag +识别的比较研究已经进行了离子测试以评估溶液参数对ZnPc作为荧光受体的选择性传感能力的影响。在异金属离子存在下加入Ag +离子后，通过基于ZnPc荧光猝灭的荧光荧光滴定法研究了干扰效应。研究了通过荧光猝灭/增强作用用Na 2 S滴定进行逐步络合/解络循环，以建立ZnPc对Ag +离子的可逆响应速率和可重复使用性。 基于锌酞菁的H型聚集选择性测定银离子

  DOI：

  10.1007/s10895-020-02520-3

文献信息

• Highly selective thioalcohol modified phthalocyanine sensors for Ag(i) and Pd(ii) based on target induced J- and H-type aggregations: synthesis, electrochemistry and peripheral metal ion binding studies
  作者：Ahmet T. Bilgiçli、Armağan Günsel、Mehmet Kandaz、A. Rıza Özkaya

  DOI：10.1039/c2dt30244f

  日期：——

  We have described highly selective 1(4),8(11),15(18),22(25)-(1-hydroxyhexan-3-ylthio)-phthalocyanine sensors, MPc[α-SCH(C3H7)(C2H5OH)]4} (MPc(α-HHT)4, where M = Zn(II) (2), Cu(II ) (3) or Co(II ) (4) and HHT: –SCH(C3H7)(C2H5OH)). The formation of S–M–S S = sulfur; M = Ag(I) or Pd(II)} bonds on the periphery in the case of Ag(I) and Pd(II) metal ions induces H- or J-aggregation, respectively, which results in significant changes in the absorption of the B- and, in particular, the Q-band. The binding ratios of Ag(I) to the periphery of 2 and 3 were found to be ca. 2 : 1 and 3 : 2, respectively. On the other hand, the binding ratios of Pd(II) to the periphery of the same compounds were found to be 3 : 1 and 4 : 1. The fluorescence of 2 exhibited distinct changes in response to treatment with Ag(I) and Pd(II) ions in solution. The fluorescence spectra emission intensity of 2 was quenched upon titration with Ag(I) and Pd(II) and a new emission maximum was observed upon titration with Pd(II). FTIR, 1H-NMR, 13C-NMR, UV–vis, MALDI-TOF MS and elemental analysis data were used to characterize the novel compounds. Transmission electron microscopy (TEM) and field-emission scanning electron microscopy (FE-SEM) were also used as complementary techniques to investigate the morphology and to image the interfacial aggregates of 2. The redox behaviours of the complexes were examined by voltammetry and in situ spectroelectrochemistry on Pt in a nonaqueous medium.

  我们描述了高选择性 1(4)、8(11)、15(18)、22(25)-(1-羟基己-3-硫基)-酞菁传感器 MPc[α-SCH(C3H7)(C2H5OH)]4} (MPc(α-HHT)4，其中 M = Zn(II) (2)、Cu(II ) (3) 或 Co(II ) (4)，HHT：-SCH(C3H7)(C2H5OH))。在 Ag(I) 和 Pd(II) 金属离子的外围形成的 S-M-S S = 硫；M = Ag(I) 或 Pd(II)} 键分别诱导 H- 或 J-聚集，从而导致 B 波段，尤其是 Q 波段的吸收发生显著变化。研究发现，Ag(I) 与 2 和 3 外围的结合率约为 2 : 3。2 :1 和 3 : 2。另一方面，钯（II）与相同化合物外围的结合率分别为 3 : 1 和 4 : 2：1 和 4 ：1.2 的荧光在溶液中与 Ag(I) 和 Pd(II) 离子的反应中表现出明显的变化。在用 Ag（I）和 Pd（II）滴定时，2 的荧光光谱发射强度被淬灭，而在用 Pd（II）滴定时，观察到了新的发射最大值。傅立叶变换红外光谱、1H-NMR、13C-NMR、紫外-可见光谱、MALDI-TOF MS 和元素分析数据用于表征这些新型化合物。此外，还使用了透射电子显微镜 (TEM) 和场发射扫描电子显微镜 (FE-SEM) 作为辅助技术来研究 2 的形态并对其界面聚集体进行成像。
• Synthesis, H- or J-type aggregations, electrochemistry and in situ spectroelectrochemistry of metal ion sensing lead(II) phthalocyanines
  作者：Armağan Günsel、Meryem N. Yaraşir、Mehmet Kandaz、Atıf Koca

  DOI：10.1016/j.poly.2010.09.035

  日期：2010.12

  We report, in this study, peripherally 3- and 4-substituted functionalized ionophore ligands (1-3) and their alpha- and beta-tetra polyalcohol substituted lead(II) phthalocyanines MPc[S-CH(C3H7)(C2FH5OH)](4)} (7, 9 and 11) and MPc(S-C6H12(OH)](4)) (8. 10 and 12) which are a mixture of different isomers. The complexes have been fully characterized by elemental analysis, FT-IR, H-1 NMR, C-13 NMR, MS (MALDI-TOF) and UV-Vis spectral data. These complexes induced H-type (face-to-face fashion) on-aggregate (edgeto-edge) dimers when titrated with AgNO3 or Na2PdCl4 in a THF-MeOH solution. Cyclic and square wave voltammetry studies showed that the complexes gave three one-electron ligand-based reductions and two one-electron oxidation couples having diffusion controlled mass transfer character. Assignments of these redox couples were confirmed by spectroelectrochemical measurements. The observation of split Q bands, which are characteristic spectral behavior of metal-free phthalocyanines, indicates demetallization of the complexes during the spectroelectrochemical measurement under the applied potentials. The types of the substituents on the ring of the phthalocyanines affect the demetallization process of the complexes. (C) 2010 Elsevier Ltd. All rights reserved.
• Elucidation of Selectivity for Silver Ion Based on Metal-Induced H-Type Aggregation of Fluorescent Receptor
  作者：Taner Arslan、Merve Umutlu、Orhan Güney

  DOI：10.1007/s10895-020-02520-3

  日期：2020.3

  fluorescence quenching of ZnPc upon addition of Ag+ ion in the presence of foreign metal ions. Stepwise complexation/decomplexation cycles with Na2S-titration by fluorescence quenching/enhancement were investigated to establish the reversible response rate and reusability of ZnPc toward Ag+ ions. Selective determination of silver ion based on H-type aggregation of zinc phthalocyanine

  在目前的工作中，通过亲核取代反应制备了一种新的取代邻苯二甲腈衍生物，然后通过环四聚合成了具有四个外围1-羟基己-3--3-硫基的高可溶性酞菁锌（ZnPc），并通过FTIR，1 H和13 C进行了表征。NMR光谱学，荧光和紫外可见测量。在具有不同组成的乙醇/水混合溶剂中阐明了ZnPc的光学性质和量子产率。获得了在不存在和存在Ag +离子的情况下ZnPc的pH依赖性荧光和吸收光谱，以阐明便于在预定混合物中稳定形成络合物的最佳pH值。Ag +识别的比较研究已经进行了离子测试以评估溶液参数对ZnPc作为荧光受体的选择性传感能力的影响。在异金属离子存在下加入Ag +离子后，通过基于ZnPc荧光猝灭的荧光荧光滴定法研究了干扰效应。研究了通过荧光猝灭/增强作用用Na 2 S滴定进行逐步络合/解络循环，以建立ZnPc对Ag +离子的可逆响应速率和可重复使用性。 基于锌酞菁的H型聚集选择性测定银离子