1,2-dicyano-4-octylsulfonylbenzene | 218598-82-4

• 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: 1,2-dicyano-4-octylsulfonylbenzene
• 英文别名: 4-n-octylsulfonyl phthalonitrile；4-n-octylsulfonylphthalonitrile；4-Octylsulfonylbenzene-1,2-dicarbonitrile
• CAS: 218598-82-4
• 化学式: C₁₆H₂₀N₂O₂S
• 分子量: 304.413
• InChiKey: PGGGUGJVICEUJA-UHFFFAOYSA-N

物化性质

• 沸点：
  516.0±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 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：
  90.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三氯化硼 、 1,2-dicyano-4-octylsulfonylbenzene 在 1-氯萘 作用下， 以13%的产率得到chloro[2,9,16(2,9,17)-trioctylsulfonylsubphthalocyaninato]boron(III)
  参考文献：
  名称：

  Synthesis and Nonlinear Optical, Photophysical, and Electrochemical Properties of Subphthalocyanines

  摘要：

  Novel boron(III) subphthalocyanines (SubPcs) soluble in organic solvents containing a variety of donor and acceptor substituent groups have been synthesized by boron trihalide-induced cyclotrimerization of adequately substituted derivatives of phthalonitrile in 1-chloronaphthalene. The choice of the substituents on the 1,2-dicyanobenzene derivatives has been made taking into account the high reactivity of the Lewis acid BCl3 toward many functional groups. Considering this limitation. we set out to synthesize phthalodinitriles equipped with iodo, nitro, alkyl- or arylthio, alkyl- or arylsulfonyl groups that are sufficiently stable under the required reaction conditions and also provide an easily accessible set of acceptor/donor substituents. The quadratic and cubic hyperpolarizabilities of these compounds as well as their linear optical and electrochemical properties have been measured by several techniques, including EFISH (at two wavelengths), HRS, and THG, steady-state and time-resolved absorption and fluorescence, laser-induced optoacoustic calorimetry, time-resolved near-infrared emission spectroscopy, and cyclic voltammetry. beta(HRS) has been measured at 1.46 mu m, where the contamination from the multiphoton-induced fluorescence can be ruled out. beta(HRS) reachs high values that markedly depend on substitution. It shows a clear enhancement with the acceptor character of the substituents, the highest values being obtained for the compounds bearing the strongest acceptor groups. They are comparable or even superior to many efficient second-order compounds. A main outcome of these results is that an adequate choice of the substituents offers a promising route for optimization of the quadratic response of the SubPcs. This kind of compounds is less prone to aggregation than their expanded analogues, the phthalocyanines, fluoresces with quantum yields ca. 0.25, lower than those typical for phthalocyanines, and has larger triplet quantum yields. The tripler-state lifetime is in the 100-mu s time range, long enough for efficient oxygen quenching. Indeed, subphthalocyanines sensitize singlet molecular oxygen, O-2((1)Delta(g)), with quantum yields ranging from 0.23 to 0.75. The ground-state oxidation potentials an similar to those of phthalocyanines, while the reduction potentials are clearly more negative; i.e., they are more difficult to reduce. In contrast, electronically excited subphthalocyanines are more easily oxidized than the corresponding phthalocyanines by ca. 500 mV which results in lower photostability, especially in polar solvents.

  DOI：

  10.1021/ja980508q
• 作为产物：
  描述：

  4-octylthiobenzene-1,2-dicarbonitrile 在 sodium tungstate 双氧水 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以91%的产率得到1,2-dicyano-4-octylsulfonylbenzene
  参考文献：
  名称：

  Phthalocyanine compound based-organic semiconductor

  摘要：

  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。

  公开号：

  US07947826B2

文献信息

• 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。
• Two-photon absorption decolorizable material, two-photon absorption refractive index modulation material, two-photon absorption polymerization material, two-photon absorption polymerization method and three-dimensional optical recording material
  申请人：Takizawa Hiroo

  公开号：US20060083890A1

  公开（公告）日：2006-04-20

  A two-photon absorption decolorizable material comprising: a two-photon absorption dye executing a two-photon absorption; and a decolorizable dye having a molar absorption coefficient equal to or less than 100 at a wavelength of a light irradiated at the two-photon absorption, wherein the decolorizable dye is decolorized by an electron transfer or an energy transfer utilizing an excitation energy obtained by the two-photon absorption of the two-photon absorption dye.

  一种双光子吸收可脱色材料，包括：具有双光子吸收的双光子吸收染料；以及在双光子吸收处照射的光波长下摩尔吸收系数等于或小于 100 的可脱色染料，其中，利用双光子吸收染料的双光子吸收所获得的激发能量，通过电子转移或能量转移对可脱色染料进行脱色。
• US7582391B2
  申请人：——

  公开号：US7582391B2

  公开（公告）日：2009-09-01
• US7947826B2
  申请人：——

  公开号：US7947826B2

  公开（公告）日：2011-05-24