4-octylthiobenzene-1,2-dicarbonitrile | 120542-26-9

• 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-octylthiobenzene-1,2-dicarbonitrile
• 英文别名: 1,2-dicyano-4-octylthiobenzene；4-octylthiophthalonitrile；4-n-octylthiophthalonitrile；4-octylsulfanylbenzene-1,2-dicarbonitrile
• CAS: 120542-26-9
• 化学式: C₁₆H₂₀N₂S
• 分子量: 272.414
• InChiKey: IDRPTJJXSGHOKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-octylthiobenzene-1,2-dicarbonitrile 在 六甲基二硅氮烷 、 zinc dibromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以66%的产率得到
  参考文献：
  名称：

  Novel Synthesis of Phthalocyanines from Phthalonitriles under Mild Conditions

  摘要：

  通过在 100 °C 的 DMF 中使用金属盐和六甲基二硅氮烷 (HMDS) 进行处理，可以方便地从邻苯二腈中制备酞菁。该反应提供了一种在温和条件下制备多种金属酞菁和取代酞菁以及锌萘酞菁的新方法。

  DOI：

  10.1055/s-2002-34237
• 作为产物：
  描述：

  1-辛硫醇 、 4-硝基邻苯二甲腈 在 四丁基溴化铵 作用下， 反应 16.0h， 以77%的产率得到4-octylthiobenzene-1,2-dicarbonitrile
  参考文献：
  名称：

  离子液体中的酞菁合成：在四丁基溴化铵中制备不同取代的酞菁

  摘要：

  通过在熔融四丁基溴化铵中对合适的邻苯二甲腈前体进行亲核取代反应，制备了一系列烷硫基、烷氧基和苯氧基邻苯二甲腈。这种容易获得且廉价的离子液体也可用作这些二腈环化产生相应取代的酞菁的介质。

  DOI：

  10.1055/s-2005-861855

文献信息

• 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。
• Phthalocyanine compound; organic semiconductor and method of producing the same, electronic device, organic photoelectric conversion device, organic field-effect transistor, and organic electroluminescence device, using the compound
  申请人：Kitamura Tetsu

  公开号：US20080142790A1

  公开（公告）日：2008-06-19

  An organic semiconductor having at least one compound of formula (PC-1); and a compound represented by formula (PC-1a): wherein M is a metallic atom, or two hydrogen atoms which bond respectively to a nitrogen atom of an isoindole ring and to a nitrogen atom of an isoindoline ring; R 1 to R 16 each independently are a hydrogen atom or a substituent, in which at least two substituents of R 1 to R 16 in formula (PC-1) are two or more different substituents, and in which at least one of the substituents of R 1 to R 16 in formula (PC-1a) is a fluorine atom, and at least one of the substituents of R 1 to R 16 in formula (PC-1a) is an electron-attracting group other than a fluorine atom.

  具有至少一个化合物(PC-1)的有机半导体；以及由公式(PC-1a)表示的化合物：其中M是金属原子，或分别与异吲哚环的氮原子和异吲哚啉环的氮原子结合的两个氢原子；R1至R16各自独立地是氢原子或取代基，其中在公式(PC-1)中的R1至R16的至少两个取代基是两个或更多不同的取代基，并且在公式(PC-1a)中的R1至R16的至少一个取代基是氟原子，以及在公式(PC-1a)中的R1至R16的至少一个取代基是除氟原子以外的电子吸引基团。
• Phthalocyanine compound based-organic semiconductor
  申请人：FUJIFILM Corporation

  公开号：US07947826B2

  公开（公告）日：2011-05-24

  An organic semiconductor having at least one compound of formula (PC-1); and a compound represented by formula (PC-1a): wherein M is a metallic atom, or two hydrogen atoms which bond respectively to a nitrogen atom of an isoindole ring and to a nitrogen atom of an isoindoline ring; R1 to R16 each independently are a hydrogen atom or a substituent, in which at least two substituents of R1 to R16 in formula (PC-1) are two or more different substituents, and in which at least one of the substituents of R1 to R16 in formula (PC-1a) is a fluorine atom, and at least one of the substituents of R1 to R16 in formula (PC-1a) is an electron-attracting group other than a fluorine atom.

  具有至少一种化合物(PC-1)的有机半导体；以及由式(PC-1a)表示的化合物：其中M是金属原子，或分别与异吲哚环的一个氮原子和异吲啉环的一个氮原子结合的两个氢原子；R1至R16各自独立地是氢原子或取代基，在式(PC-1)中R1至R16的至少两个取代基是两个或更多不同的取代基，并且在式(PC-1a)中R1至R16的至少一个取代基是氟原子，式(PC-1a)中R1至R16的至少一个取代基是除氟原子之外的电子吸引基团。
• Optical Layer including mu-oxo-bridged boron-subphthalocyanine dimer
  申请人：Mori Tomohiro

  公开号：US20080210128A1

  公开（公告）日：2008-09-04

  An optical layer comprises μ-oxo-bridged boron subphthalocyanine dimer. The μ-oxo-bridged boron subphthalocyanine dimer is represented by the following chemical formula (1). (In the chemical formula (1), Z 1 to Z 12 are the same or different to each other and selected from the groups consisting of a hydrogen atom, a hydroxyl group, a mercapto group, an alkyl group, an aralkyl group, an aryl group, an amino group, an alkoxyl group and a thioether group. Z 1 to Z 12 have one or more substitutional groups or have no substitutional group.)

  一个光学层包括μ-氧桥联硼次酞菁二聚体。μ-氧桥联硼次酞菁二聚体由以下化学式（1）表示。(在化学式（1）中，Z1到Z12彼此相同或不同，选自包括氢原子、羟基、巯基、烷基、芳基、芳基烷基、芳基、氨基、烷氧基和硫醚基的基团。Z1到Z12具有一个或多个取代基或无取代基。)
• Synthesis of Unsymmetrically Substituted Subphthalocyanines
  作者：Christian G. Claessens、Tomás Torres

  DOI：10.1002/1521-3765(20000616)6:12<2168::aid-chem2168>3.0.co;2-n

  日期：2000.6.16

  A series of new unsymmetrically substituted subphthalocyanines containing iodo or octylthioether substituents on the outer aromatic rings have been synthesized. The statistical reaction of one equivalent of 1,2-dicyano-3-iodobenzene whether with two equivalents of 1,2-dicyano-4-octylthiobenzene or with two equivalents of 1,2dicyano-4,5-dioctylthiobenzene in the presence of boron trichloride in 1-chloronaphthalene

  合成了一系列在外芳环上含有碘或辛基硫醚取代基的新的不对称取代的亚酞菁。在三氯化硼的存在下，一当量的1,2-二氰基-3-碘苯与两当量的1,2-二氰基-4-辛基硫苯或两当量的1,2-二氰基-4,5-二辛基硫苯的统计反应在两种情况下，在1-氯萘中生成的所有可能的预期的不对称取代的亚酞菁均通过硅胶上的柱色谱法分离。所有化合物均通过FAB质谱鉴定，然后通过HR-LSIMS光谱鉴定。