octa-3,6-(4-methylphenylthio) dihydro phthalocyanine | 101367-20-8

• 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: octa-3,6-(4-methylphenylthio) dihydro phthalocyanine
• 英文别名: tetrakis[1,4-bis(4-methylthiophenyl)]phthalocyanine；5,8,14,17,23,26,32,35-Octakis[(4-methylphenyl)sulfanyl]-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；5,8,14,17,23,26,32,35-octakis[(4-methylphenyl)sulfanyl]-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: 101367-20-8
• 化学式: C₈₈H₆₆N₈S₈
• 分子量: 1492.07
• InChiKey: DKFDQUGLTNCUJI-UHFFFAOYSA-N

物化性质

• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  25.8
• 重原子数：
  104
• 可旋转键数：
  16
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  311
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  octa-3,6-(4-methylphenylthio) dihydro phthalocyanine 在 copper diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以94%的产率得到1,4,8,11,15,18,22,25-octakis(methylthiophenyl)phthalocyanine
  参考文献：
  名称：

  EP2404970

  摘要：

  公开号：
• 作为产物：
  描述：

  3,6-bis(metylthiophenyl)phthalonitrile 以 戊醇 为溶剂， 反应 7.0h， 以19%的产率得到octa-3,6-(4-methylphenylthio) dihydro phthalocyanine
  参考文献：
  名称：

  Syntheses of near infrared absorbed phthalocyanines to utilize photosensitizers

  摘要：

  酞菁作为功能着色剂，在各种应用领域都引起了极大的兴趣。为了实现各种应用，尤其是光敏剂的应用，需要将酞菁的最大吸收波段（Q 波段）转移到近红外区域。我们合成了取代的酞菁类似物烷基苯并吡啶卟嗪，特别是双(1,4-二癸基苯并)-双(3,4-吡啶)卟嗪锌，以及具有氨基树枝状侧链的环状酞菁，如环状多(氨基胺)酞菁树枝状锌。据报道，这两种类型的酞菁可作为光敏剂用于癌症的光动力疗法。利用激光闪烁光解法估算了双(1,4-二癸基苯并)-双(3,4-吡啶并)卟吩锌及其区域异构体各自的癌症光动力疗法疗效。利用癌细胞培养物评估了环状锌聚(氨基胺)酞菁树枝体使用光动力疗法的能力。这两种酞菁都适合用作光敏剂，对癌症进行光动力治疗。还合成了 1,4,8,11,15,18,22,25-八(噻吩甲氧基)酞菁和 1,4,8,11,15,18,22,25-八(噻吩叔丁基)酞菁，以开发新一代光伏电池和/或染料敏化太阳能电池。非周边取代的 1,4,8,11,15,18,22,25-八(硫代芳基)酞菁在近红外区域显示出 Q 波段。对上述 1,4,8,11,15,18,22,25-辛二基（硫芳基）酞菁进行了电化学测量，以研究它们的电子转移能力和电化学机制。预计 1,4,8,11,15,18,22,25-辛二基（硫芳基）酞菁化合物将成为下一代光伏电池的合适材料。

  DOI：

  10.1142/s1088424613500326

文献信息

• [EN] METALOXYPHTHALOCYANINE COMPOUNDS<br/>[FR] COMPOSES DE METALOXYPHTALOCYANINE
  申请人：AVECIA LTD

  公开号：WO2004020529A1

  公开（公告）日：2004-03-11

  A phthalocyanine compound of Formula (I) wherein M is an oxymetal group, methods and uses involving these compounds.

  一种配方（I）的邻苯二甲酸酞菁化合物，其中M是一个氧化金属基团，涉及这些化合物的方法和用途。
• 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。
• Syntheses of near infrared absorbed phthalocyanines to utilize photosensitizers
  作者：Keiichi Sakamoto、Satoru Yoshino、Makoto Takemoto、Naoki Furuya

  DOI：10.1142/s1088424613500326

  日期：2013.8

  Phthalocyanines have become of major interest as functional colorants for various applications. In order to use various applications especially photosensitizers, the absorption maxima called Q-band of phthalocyanines are required to be shifted to the near infrared region. Substituted phthalocyanine analog alkylbenzopiridoporphyrazins, especially zinc bis(1,4-didecylbenzo)-bis(3,4-pyrido)porphyrazine, and toroidal-shaped phthalocyanines having aminoamine dendric side chains such as toroidal zinc poly(aminoamine)phthalocyanine dendrons were synthesized. Phthalocyanines of two types reportedly use photosensitizers for photodynamic therapy of cancer. The respective efficacies of photodynamic therapy of cancer for zinc bis(1,4-didecylbenzo)-bis(3,4-pyrido)porphyrazine and its regioisomers were estimated using laser-flash photolysis. The capability of using photodynamic therapy for toroidal zinc poly(aminoamine)phthalocyanine dendrons was assessed using a cancer cell culture. Both phthalocyanines were suitable for the use as a photosensitizer as photodynamic therapy of cancer. Then, non-peripheral thioaryl substituted phthalocyanines, 1,4,8,11,15,18,22,25-octakis(thioaryl)phthalocyanines, such as 1,4,8,11,15,18,22,25-octakis(thiophenylmethyl)phthalocyanines, 1,4,8,11,15,18,22,25-octakis(thiophenylmethoxy)phthalocyanines, and 1,4,8,11,15,18,22,25-octakis(thiophenyl tert-butyl)phthalocyanines were also synthesized in order to develop next- generation photovoltaic cells and/or dye-sensitized solar cells. Non-peripheral substituted 1,4,8,11,15,18,22,25-octakis(thioaryl)phthalocyanines exhibited a Q-band in the near infrared region. Electrochemical measurements were performed on the above-mentioned 1,4,8,11,15,18,22,25-octakis(thioaryl)phthalocyanines described above to examine their electron transfer abilities and electrochemical mechanisms. The compounds 1,4,8,11,15,18,22,25-octakis(thioaryl)phthalocyanines are anticipated to be appropriate materials for use in the next generation of photovoltaic cells.

  酞菁作为功能着色剂，在各种应用领域都引起了极大的兴趣。为了实现各种应用，尤其是光敏剂的应用，需要将酞菁的最大吸收波段（Q 波段）转移到近红外区域。我们合成了取代的酞菁类似物烷基苯并吡啶卟嗪，特别是双(1,4-二癸基苯并)-双(3,4-吡啶)卟嗪锌，以及具有氨基树枝状侧链的环状酞菁，如环状多(氨基胺)酞菁树枝状锌。据报道，这两种类型的酞菁可作为光敏剂用于癌症的光动力疗法。利用激光闪烁光解法估算了双(1,4-二癸基苯并)-双(3,4-吡啶并)卟吩锌及其区域异构体各自的癌症光动力疗法疗效。利用癌细胞培养物评估了环状锌聚(氨基胺)酞菁树枝体使用光动力疗法的能力。这两种酞菁都适合用作光敏剂，对癌症进行光动力治疗。还合成了 1,4,8,11,15,18,22,25-八(噻吩甲氧基)酞菁和 1,4,8,11,15,18,22,25-八(噻吩叔丁基)酞菁，以开发新一代光伏电池和/或染料敏化太阳能电池。非周边取代的 1,4,8,11,15,18,22,25-八(硫代芳基)酞菁在近红外区域显示出 Q 波段。对上述 1,4,8,11,15,18,22,25-辛二基（硫芳基）酞菁进行了电化学测量，以研究它们的电子转移能力和电化学机制。预计 1,4,8,11,15,18,22,25-辛二基（硫芳基）酞菁化合物将成为下一代光伏电池的合适材料。
• WO2007/2981
  申请人：——

  公开号：——

  公开（公告）日：——
• Red-shifted water dispersible IR dyes
  申请人：Vonwiller Charlotte Simone

  公开号：US20070010645A1

  公开（公告）日：2007-01-11

  A phthalocyanine dye of formula (I) is provided: wherein M is a metal group or is absent; Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 are selected from phenyl, naphthyl, pyridyl, furanyl, pyrollyl or thiophenyl, each of Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 being optionally substituted with 1, 2, 3, 4 or 5 groups, the or each group being independently selected from C 1-12 alkyl, C 1-12 alkoxy, C 1-12 arylalkyl, C 1-12 arylalkoxy, —(OCH 2 CH 2 ) d OR d , cyano, halogen, amino, hydroxyl, thiol, —SR v , —NR u R v , nitro, phenyl, phenoxy, —CO 2 R v , —C(O)R v , —OCOR v , —SO 2 R v , —OSO 2 R v , —NHC(O)R v , —CONR u R v , —CONR u R v , sulfonic acid, sulfonic acid salt and sulfonamide; d is an integer from 2 to 5000; R d is H, C 1-8 alkyl or C(O)C 1-8 alkyl; R u and R v are independently selected from hydrogen, C 1-12 alkyl, phenyl or phenyl-C 1-8 alkyl; wherein at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 is substituted with a sulfonic acid, a sulfonic acid salt or a sulfonamide group. Dyes of this type are especially suitable for use in netpage and Hyperlabel™ systems.