3-(2-diethylaminoethanethiol) phthalonitrile | 135412-21-4

• 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-(2-diethylaminoethanethiol) phthalonitrile
• 英文别名: 3-diethylaminoethylsulfanyl phthalonitrile；3-(2-diethylaminoethylthio)phthalonitrile；diethylaminoethylthiol phthalonitrile；3-[2-(diethylamino)ethylsulfanyl]benzene-1,2-dicarbonitrile
• CAS: 135412-21-4
• 化学式: C₁₄H₁₇N₃S
• 分子量: 259.375
• InChiKey: WDUJANYUJRNTHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  50.82
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(2-diethylaminoethanethiol) phthalonitrile 、 iron(II) chloride 在 2-diethylaminoethanol 作用下， 以 further solvent(s) 为溶剂， 以74%的产率得到iron(II)tetrakis-(2-diethylaminpethanethio)phthalocyanine
  参考文献：
  名称：

  四取代钴，铁和锰烷硫基酞菁配合物的自组装单层膜的表面性能

  摘要：

  铁（SAM- 1），钴（SAM- 2）和锰（SAM- 3）酞菁配合物的自组装单层（SAM）膜在非外围位置被二乙基氨基乙硫四取代，形成于二甲基甲酰胺（DMF）。研究了SAM膜的电化学，阻挡和表面性能。循环伏安法用于研究薄膜的电化学性能。薄膜抑制裸金表面上常见的法拉第过程的能力（金氧化，[Fe（H 2 O）6 ] 3+ / [Fe（H 2 O）6 ] 2+的溶液氧化还原化学并研究了铜的欠电位沉积（UDP）。电化学阻抗谱（EIS），使用[Fe（CN）6 ] 3- / 4-氧化还原过程作为探针，提供了对膜/电极界面电特性的见解。使用原子力显微镜（AFM）和扫描电子显微镜（SEM）探测薄膜的表面性能。该薄膜被用于农药呋喃丹的电催化氧化。相对于在裸金电极上观察到的结果，从电流信号增强和农药在每张膜上的正氧化电势降低证明了电催化作用。利用转盘电极伏安法研究了农药的电催化氧化机理。

  DOI：

  10.1016/j.electacta.2010.06.065
• 作为产物：
  描述：

  3-硝基邻苯二腈 、 2-二乙氨基乙硫醇盐酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到3-(2-diethylaminoethanethiol) phthalonitrile
  参考文献：
  名称：

  取代基的位置和性质对新型钴酞菁配合物的光谱，电化学和光谱电化学性质的影响研究与合成

  摘要：

  摘要报道了新的酞菁钴配合物的合成，该配合物在外围（配合物3a）和非外围（配合物3b）位置被二乙基氨基乙硫四取代，在非外围位置（配合物5）被苄硫醇四取代。 。研究了取代基的性质和位置对这些配合物的光谱，电化学和光谱电化学性质的影响。配合物3a的溶液电化学显示出三个明显分辨的氧化还原过程，归因于Co III Pc -2 / Co II Pc -2（E½= +0.64 V vs Ag | AgCl），Co II Pc -2 / Co I Pc -2（E相对于Ag | AgCl为1/2 = -0.24 V）和Co I Pc -2 / Co I Pc-3（相对于Ag | AgCl为E½= -1.26 V）。在络合物3a中未观察到环氧化。配合物3b均显示了环基氧化，归因于Co III Pc -1 / Co III Pc -2物种（E p = +0.86 V对Ag | AgCl），以及与Co I Pc -2

  DOI：

  10.1016/j.poly.2010.01.004

文献信息

• Synthesis, photophysical and photochemical studies of water soluble cationic zinc phthalocyanine derivatives
  作者：Mopelola Idowu、Tebello Nyokong

  DOI：10.1016/j.poly.2008.11.021

  日期：2009.2

  Peripherally and non-peripherally 2-diethylaminoethanethiol tetra-substituted zinc phthalocyanine (5a and 6a) and their quaternized derivatives (5b and 6b) have been synthesized and characterized. The quaternized derivatives (5b and 6b) show excellent solubility in aqueous medium. The photophysical and photochemical properties of the 2-diethylaminoethanethiol appended zinc phthalocyanine in dimethylsulfoxide (DMSO) for the non-ionic (5a and 6a) and in both DMSO and aqueous medium (phosphate buffered saline solution PBS, pH 7.4) (in the presence and absence of cremophore EL (CEL)) for the quaternized (5b and 6b) derivatives were studied and compared with that of the peripherally octa-substituted derivatives (7a and 7b). The complexes have intense absorption in the visible/near-IR region though the quaternized forms (5b, 6b and 7b) were slightly blue shifted and highly aggregate in aqueous solution. The triplet state quantum yields (Phi(T)) and the triplet lifetimes (tau(T)) were found to be higher in DMSO (Phi(T) values ranged from 0.57 to 0.75 while tau(T) values ranged from 190 to 220 mu s in DMSO for all complexes) compared to aqueous medium (Phi(T) values ranged from 0.15 to 0.17 while tau(T) values ranged from 20 to 70 mu s in pH 7.4 buffer). Addition of cremophore EL in aqueous solution resulted in induced disaggregation leading to increased Phi(T) and tau(T). (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and photophysicochemical properties of novel zinc phthalocyanines mono substituted with carboxyl containing functional groups
  作者：Nomasonto Rapulenyane、Edith Antunes、Nkosiphile Masilela、Tebello Nyokong

  DOI：10.1016/j.jphotochem.2012.09.007

  日期：2012.12

  This work reports on the synthesis and the physicochemical properties of novel unsymmetrically substituted zinc phthalocyanines (complexes 8,10 and 11) and their symmetrically substituted counterparts (complexes 9,12 and 13). The new complexes and their counterparts were successfully structurally characterized by IR, NMR, mass spectral and elemental analyses. Low fluorescence quantum yields (0.032) and lifetimes (0.91 ns) were obtained for the symmetrical ZnOTPc (complex 9) compared to the higher fluorescence quantum yields (0.15, 0.13, 0.10, 0.09 and 0.29) and lifetimes (4.4, 1.69, 1.69, 2.16 and 3.23 ns) obtained for ZnMPCPc (8), ZnTDTPc (12), ZnMCapPc (10), ZnMCafPc (11) and ZnTCPPc (13), respectively. All the complexes showed the ability to produce singlet oxygen with the highest triplet quantum yields obtained for 8 and 10(0.80 and 0.65 respectively). High triplet lifetimes (109-286 mu s) were obtained for all complexes. Complex 8 showed the longest triplet and fluorescence lifetimes as well the largest triplet state and singlet oxygen quantum yields. (C) 2012 Elsevier B.V. All rights reserved.
• The effects of point of substitution on the electrochemical behavior of new manganese phthalocyanines, tetra-substituted with diethylaminoethanethiol
  作者：Isaac Adebayo Akinbulu、Tebello Nyokong

  DOI：10.1016/j.ica.2010.06.003

  日期：2010.10

  The syntheses and comparative studies of the spectral, voltammetry and spectroelectrochemical properties of new manganese phthalocyanine complexes, tetra-substituted with diethylaminoethanethio at the peripheral (complex 3a) and non-peripheral positions (complex 3b) are reported. Solution electrochemistry of complex 3a showed quasi-reversible metal-based ((MnPc-2)-Pc-III/(MnPc-2)-Pc-II, E-1/2 = -0.07 V vs. Ag vertical bar AgCl) and ring-based ((MnPc-2)-Pc-II/MnIIPc-3, E-1/2 = -0.78 V vs. Ag vertical bar AgCl) reductions, but no ring-based oxidation. However, complex 3b showed weak irreversible ring-oxidation signal (Ep = +0.86 vs. Ag vertical bar AgCl). Reversible metal-based ((MnPc-2)-Pc-III/(MnPc-2)-Pc-II, E-1/2 = -0.04 V vs. Ag vertical bar AgCl) and ring-based ((MnPc-2)-Pc-II/MnIIPc-3, E-1/2 = -0.68 V vs. Ag vertical bar AgCl) reductions were also observed for complex 3b. Spectroelectrochemistry was used to confirm these processes. Reduction process involving the metal ((MnPc-2)-Pc-III/(MnPc-2)-Pc-II) was associated with the formation of manganese l-oxo complex in complex 3a. (C) 2010 Elsevier B.V. All rights reserved.