2,3,9,10,16,17,23,24-octakis(pentylthio)phthalocyanine | 1190872-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 2,3,9,10,16,17,23,24-octakis(pentylthio)phthalocyanine
• 英文别名: 6,7,15,16,24,25,33,34-Octakis(pentylsulfanyl)-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；6,7,15,16,24,25,33,34-octakis(pentylsulfanyl)-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
• CAS: 1190872-33-3
• 化学式: C₇₂H₉₈N₈S₈
• 分子量: 1332.15
• InChiKey: NXUDDMJDUAXWNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  24.8
• 重原子数：
  88
• 可旋转键数：
  40
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  311
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1-戊硫醇 在 辛醇 、 lithium 、 caesium carbonate 作用下， 以 1,3-二甲基-2-咪唑啉酮 为溶剂， 反应 120.0h， 生成 2,3,9,10,16,17,23,24-octakis(pentylthio)phthalocyanine
  参考文献：
  名称：

  Halide effect in electron rich and deficient discotic phthalocyanines

  摘要：

  合成了一系列盘形八烷基和四烷基硫取代的酞菁，包含四个氯、溴、碘原子或十二个氟原子。所有化合物均表现出柱状介晶性，已通过偏振光显微镜、热分析和变温X射线衍射确认。含卤素原子的酞菁不结晶，而是形成玻璃态或部分结晶的六角柱状相。玻璃转变温度随着卤素原子尺寸的增大和烷基链长度的缩短而升高。相对而言，所有八烷基和四烷基硫取代的酞菁均可结晶，且具有C5–7的烷基链长度的八取代衍生物显示出倾斜（矩形）柱状介晶相。利用循环伏安、差分脉冲伏安、紫外-可见光谱法及DFT水平的量子化学计算来确定所有合成的和一些参考酞菁的前沿轨道能量。八烷基和四烷基硫取代的酞菁是典型的p型半导体，引入四个氯、溴或碘原子仅使前沿轨道能量降低至多0.1 eV，光学带隙降低至多0.03 eV。氟化酞菁的LUMO能量显著降低0.5 eV，降至约−4 eV，这一数值恰好位于有机n型半导体的临界值，可能在空气中稳定。

  DOI：

  10.1039/b917169j

文献信息

• Photophysical and photochemical properties of Ni(II), Pd(II) and Pt(II) aryloxo and alkylthio derivatised phthalocyanine
  作者：Taofeek B. Ogunbayo、Tebello Nyokong

  DOI：10.1016/j.molstruc.2010.03.047

  日期：2010.6

  Several aryloxo (3a-6a and 3b-6b) and alkylthio (3d and 3e) derivatised phthalocyanines were synthesized, characterized and the photochemical and photophysical properties investigated along with those of the previously reported (3c-5c, 4d, 5d, 4e and 5e) complexes. The effects of open-shell metals (Ni(II), Pd(II) and Pt(II)) on the photophysical and photochemical properties of the phthalocyanine ligands were investigated. Palladium and platinum improved the triplet quantum yield and singlet oxygen generation capacities of the unmetalated phthalocyanines (3a-3e) making their complexes candidates for further investigation in photocatalysis. Ni(II)Pc analogues gave poor results compared with their Pd(II)Pc and Pt(II)Pc counterparts. (C) 2010 Elsevier B.V. All rights reserved.
• Halide effect in electron rich and deficient discotic phthalocyanines
  作者：Mohamed Ahmida、Raymond Larocque、M. Sharif Ahmed、Alina Vacaru、Bertrand Donnio、Daniel Guillon、S. Holger Eichhorn

  DOI：10.1039/b917169j

  日期：——

  A series of discotic octa- and tetra-alkylthio substituted phthalocyanines containing four Cl, Br, I atoms or twelve fluorine atoms have been prepared. All compounds display columnar mesomorphism as confirmed by polarized optical microscopy, thermal analysis, and variable temperature X-ray diffraction. Phthalocyanines containing halide atoms do not crystallize but form glassy or partially crystalline hexagonal columnar phases. Glass transition temperatures increase with increasing size of the halide atoms and with decreasing length of the alkyl chains. In contrast, all octa- and tetra-alkylthio substituted phthalocyanines crystallize and octa-substituted derivatives with aliphatic chain lengths of C5–7 exhibit tilted (rectangular) columnar mesophases. Cyclic and differential pulse voltammetry, UV-Vis spectroscopy, and quantum chemical calculations at the DFT level have been employed to determine frontier orbital energies of all synthesized and some reference phthalocyanines. Octa- and tetra-alkylthio substituted phthalocyanines are typical p-type semiconductors and the introduction of four Cl, Br, or I atoms lowers frontier orbital energies by only up to 0.1 eV and the optical gap by up to 0.03 eV. A significant decrease in LUMO energy by 0.5 eV to about −4 eV is observed for the fluorinated phthalocyanine, which is a value right at the border of organic n-type semiconductors that may be stable in air.

  合成了一系列盘形八烷基和四烷基硫取代的酞菁，包含四个氯、溴、碘原子或十二个氟原子。所有化合物均表现出柱状介晶性，已通过偏振光显微镜、热分析和变温X射线衍射确认。含卤素原子的酞菁不结晶，而是形成玻璃态或部分结晶的六角柱状相。玻璃转变温度随着卤素原子尺寸的增大和烷基链长度的缩短而升高。相对而言，所有八烷基和四烷基硫取代的酞菁均可结晶，且具有C5–7的烷基链长度的八取代衍生物显示出倾斜（矩形）柱状介晶相。利用循环伏安、差分脉冲伏安、紫外-可见光谱法及DFT水平的量子化学计算来确定所有合成的和一些参考酞菁的前沿轨道能量。八烷基和四烷基硫取代的酞菁是典型的p型半导体，引入四个氯、溴或碘原子仅使前沿轨道能量降低至多0.1 eV，光学带隙降低至多0.03 eV。氟化酞菁的LUMO能量显著降低0.5 eV，降至约−4 eV，这一数值恰好位于有机n型半导体的临界值，可能在空气中稳定。