3,6-di(octylthiol)-4,5-dicyanobenzene | 344453-41-4

• 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: 3,6-di(octylthiol)-4,5-dicyanobenzene
• 英文别名: 3,6-di(octylthio)-1,2-dicyanobenzene；3,6-di(octylthio)-4,5-dicyanobenzene；3,6-di(octylthio)-4,5-dicyazobenzene；3,6-thiooctylphthalonitrile；3,6-Bis(octylsulfanyl)benzene-1,2-dicarbonitrile
• CAS: 344453-41-4
• 化学式: C₂₄H₃₆N₂S₂
• 分子量: 416.695
• InChiKey: YPFCPDDBDOIGHD-UHFFFAOYSA-N

物化性质

• 沸点：
  544.7±50.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-di(octylthiol)-4,5-dicyanobenzene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 戊醇 为溶剂， 反应 5.0h， 以56%的产率得到palladium-1,4,8,11,15,18,22,25-octakis(octylthio)phthalocyanine
  参考文献：
  名称：

  Phototransformation of 4-nitrophenol using Pd phthalocyanines supported on single walled carbon nanotubes

  摘要：

  Adsorption of palladium phthalocyanines complexes on single walled carbon nanotubes was carried out. The resulting composites were employed as catalysts for heterogeneous photocatalytic oxidation of 4-nitrophenol (4-NP) in aqueous media. Singlet oxygen was found to be involved in the phototransformation of 4-NP. Gas chromatographic separation gave hydroquinone and benzoquinone as the phototransformation products. Langmuir-Hinshelwood (L-H) model was employed to evaluate the adsorption and desorption equilibria of the reactants and the products. 2,3,9,10,16,17,23,24-octakis(dodecylthiophthalocyaninato) palladium(II) and 1,4,8,11,15,18,22,25-octakis(dodecylthio phthalocyaninato) palladium, containing the longest alkyl chain gave the best performances. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.01.016
• 作为产物：
  描述：

  3,6-二羟基邻苯二甲腈 在 2,6-二甲基吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.0h， 生成 3,6-di(octylthiol)-4,5-dicyanobenzene
  参考文献：
  名称：

  一些 3,6-二取代邻苯二甲腈的路线和从中衍生的酞菁实例：概述

  摘要：

  本文回顾了一些合成途径，这些途径提供了 3,6-二取代酞腈，这是合成 1,4,8,11,15,18,22,25-八取代酞菁衍生物的前体。评价了使用 Diels-Alder 反应合成 3,6-二烷基、3,6-二烷氧基甲基、3,6-二烯基和 3,6-二苯基邻苯二甲腈的早期路线。然而，审查的重点集中在 2,3-二氰基氢醌作为获得 3,6-二取代邻苯二甲腈的起始原料的范围和应用。使用 2,3-二氰基氢醌的最早例子涉及其 O-烷基化以提供 3,6-二烷氧基邻苯二甲腈。这些是近红外吸收酞菁衍生物的直接前体。2,3-二氰基氢醌的三氟甲磺酸化扩展了该化合物用于合成酞菁的范围；ñAr 反应并容易与硫醇反应生成 3,6-双（烷基硫烷基）和 3,6-双（芳基硫烷基）邻苯二甲腈。3,6-双（苯基硒基）邻苯二甲腈最近也从相同的前体中获得。从中获得的酞菁衍生物通常表现出强烈的红移 Q 波段吸收，该吸收对中心金属离子特别敏感。2

  DOI：

  10.1142/s108842461330005x

文献信息

• Synthesis of near-infrared absorbed metal phthalocyanine with S-aryl groups at non-peripheral positions
  作者：Keiichi Sakamoto、Eiko Ohno-Okumura、Taku Kato、Hisashi Soga

  DOI：10.1142/s1088424610001726

  日期：2010.1

  Phthalocyanines are used as various applications, including as organic charge carriers in photocopiers, laser light absorbers in data storage systems, photoconductors in photovoltaic cells and electrochromic displays, and non-colored transparent film in visible region. The absorption maxima of phthalocyanines are best if moved near the infrared region for these applications. The Q band of phthalocyanines can be moved to bathochromic effects through extension of a π conjugation system such as naphthalocyanines and anthracyanines. Yields of naphthalocyanines and anthracyanines are, however, low. To solve the problem, novel metal phthalocyanines having non-peripheral S-aryl substituent were synthesized. The novel phthalocyanines show a high strain structure and no liquid crystal property. The target compounds were synthesized: 15 phthalocyanines from 2,3-dicyanohydroquinone in 3 steps via 1,2-dicyanobenzene-3,6-bis(trifluorate) and 1,2-dicyanobenzene-3,6-thiophenols. The Q bands of obtained compounds appeared in the near-infrared region. In particular, lead 1,4,8,11,15,18,22,25-octakis(thiophenylmethyl)phthalocyanine shows a Q band at 857 nm. Furthermore, non-colored transparent films in the visible region can be produced.

  酞菁有多种用途，包括复印机中的有机电荷载体、数据存储系统中的激光光吸收器、光伏电池和电致变色显示器中的光电导体以及可见光区域的非彩色透明薄膜。在这些应用中，酞菁的吸收最大值最好接近红外区域。通过扩展 π 共轭体系（如萘花青素和蒽花青素），可将酞菁的 Q 波段转化为浴色效应。然而，萘酞菁和蒽菁的产量很低。为了解决这个问题，我们合成了具有非外周 S-芳基取代基的新型金属酞菁。这些新型酞菁具有高应变结构，且无液晶特性。合成了目标化合物：通过 1,2-二氰基苯-3,6-双(三氟)和 1,2-二氰基苯-3,6-噻吩酚，分三步从 2,3-二氰基对苯二酚合成了 15 个酞菁。所得化合物的 Q 带出现在近红外区域。其中，1,4,8,11,15,18,22,25-八(噻吩甲基)酞菁铅在 857 纳米波长处出现了 Q 带。此外，还可以生产出可见光区域的无色透明薄膜。
• Synthesis and electrochemical characterisation of new tantalum (V) alkythio phthalocyanines
  作者：Vongani Chauke、Tebello Nyokong

  DOI：10.1016/j.ica.2010.05.003

  日期：2010.11

  The synthesis and electrochemical characterisation of octa-pentylthio (4a) and octa-octylthio (4b) – phthalocyaninato tantalum (III) hydroxide are hereby reported. These TaPc complexes absorb in the near infrared region (∼800 nm in dichloromethane). They show good solubility in most common solvents especially non-viscous solvents such as dichloromethane and chloroform. NMR, mass and infrared spectroscopy

  特此报道辛基戊硫基（4a）和辛基辛硫基（4b）–酞菁氰化钽（III）的合成和电化学表征。这些TaPc复合物在近红外区域（在二氯甲烷中约为800 nm）吸收。它们在大多数普通溶剂（特别是非粘性溶剂，例如二氯甲烷和氯仿）中显示良好的溶解性。NMR，质谱和红外光谱以及元素分析证实了合成配合物的结构和纯度。循环伏安图（CV）显示出可逆的还原对和不可逆的氧化峰。后者表现出吸附行为。在-0.74和-1.13 V（相对于Ag | AgCl电极）观察到的还原方法为图4a，对于4b，为-0.67，-1.02和-1.48 V（相对于Ag | AgCl）。光谱电化学证实一种金属还原，其余的氧化还原过程集中在酞菁环上。
• 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.
• SUBSTITUTED PHTHALOCYANINES AND THEIR PRECURSORS
  申请人：Gentian AS

  公开号：EP1238016A1

  公开（公告）日：2002-09-11
• [EN] SUBSTITUTED PHTHALOCYANINES AND THEIR PRECURSORS<br/>[FR] PHTALOCYANINES SUBSTITUEES ET LEURS PRECURSEURS
  申请人：GENTIAN AS

  公开号：WO2001042368A1

  公开（公告）日：2001-06-14

  This invention relates to a process for the preparation of phthalonitrile sulfonate esters, a process for the preparation of substituted phthalonitriles using said phthalonitrile sulfonate esters, a process for the preparation of substituted phthalocyanines using said substituted phthalonitriles, a process for the preparation of phthalonitrile halides, a process for the preparation of substituted phthalocyanines using said phthalonitrile halides, novel phthalonitrile sulfonate esters, novel substituted phthalonitriles, novel substituted phthalocyanines and certain uses of said novel substituted phthalocyanines.