2,5-didecylthiophene-1,1-dioxide | 128912-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-didecylthiophene-1,1-dioxide
• 英文别名: 2,5-Didecylthiophene 1,1-dioxide
• CAS: 128912-58-3
• 化学式: C₂₄H₄₄O₂S
• 分子量: 396.678
• InChiKey: RFEXQVNWMFFNHK-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C
• 沸点：
  528.0±17.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-didecylthiophene-1,1-dioxide 、 反丁烯二腈 以 氯仿 为溶剂， 反应 18.0h， 以25%的产率得到3,6-二癸基酞腈
  参考文献：
  名称：

  Synthesis and electrochemical characterisation of some long chain 1,4,8,11,15,18,22,25-octa-alkylated metal-free and zinc phthalocyanines possessing discotic liquid crystalline properties

  摘要：

  一系列长链（C10、C12、C15 和 C18）3,6-二烷基邻苯二甲酰亚胺经 4 个步骤由噻吩制备而成，并转化为标题酞菁的无金属锌衍生物。使用 1H NMR、MALDI-TOF ms 和溶液相电子（UV-VIS）光谱对对称大环进行了表征。在二氯甲烷或 1,2-二氯乙烷中，拥有较短烷基取代基的无金属大环的四个环基氧化还原过程的电位范围为-1.8 至 1.2 V vs. Ag/Ag+。随着 8 个烷基取代基链长的增加，可逆性变差。锌配合物的氧化还原过程不像无金属酞菁那样明确。所有化合物都表现出盘状热向性液晶行为，研究采用了偏光光学显微镜和差示扫描量热法（DSC）。最多可检测到三种不同的介相。与不含金属的化合物相比，锌衍生物在更高的温度下显示出液晶特性。无金属酞菁和带有 C12 链的锌酞菁的结晶到盘状液晶介相转变温度最低。在玻璃上浇铸的薄膜（厚度约为 1000 埃）的变温紫外-可见光谱中，获得了结晶、介相和各向同性液相化合物的光谱。各向同性液态薄膜的光谱与同一化合物溶液的光谱相似。

  DOI：

  10.1039/b006123i
• 作为产物：
  描述：

  癸基溴 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 2,5-didecylthiophene-1,1-dioxide
  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

• McKeown, Neil B.; Chambrier, Isabelle; Cook, Michael J., Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1169 - 1177
  作者：McKeown, Neil B.、Chambrier, Isabelle、Cook, Michael J.

  DOI：——

  日期：——
• MCKEOWN, NEIL B.;CHAMBRIER, ISABELLE;COOK, MICHAEL J., J. CHEM. SOC. PT 1. PERKIN TRANS.,(1990) N, C. 1169-1177
  作者：MCKEOWN, NEIL B.、CHAMBRIER, ISABELLE、COOK, MICHAEL J.

  DOI：——

  日期：——
• 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。
• Synthesis and electrochemical characterisation of some long chain 1,4,8,11,15,18,22,25-octa-alkylated metal-free and zinc phthalocyanines possessing discotic liquid crystalline properties
  作者：Jannie C. Swarts、Ernie H. G. Langner、Nina Krokeide-Hove、Michael J. Cook

  DOI：10.1039/b006123i

  日期：——

  A series of long chain (C10, C12, C15 and C18) 3,6-dialkylated phthalonitriles, prepared in 4 steps from thiophene, have been converted into the title phthalocyanines as metal-free and zinc derivatives. The symmetric macrocycles were characterised using 1H NMR, MALDI-TOF ms and solution phase electronic (UV-VIS) spectroscopy. Four ring-based redox processes for the metal-free macrocycles possessing shorter alkyl substituents could be identified in the potential range −1.8 to 1.2 V vs. Ag/Ag+ in dichloromethane or 1,2-dichloroethane. Reversibility became poorer with an increase in chain length of the eight alkyl substituents. The redox processes of the zinc complexes were not as well defined as those of the metal-free phthalocyanines. All compounds exhibited discotic thermotropic liquid crystal behaviour, which was studied using polarised optical microscopy and differential scanning calorimetry (DSC). Up to three different mesophases were detected. The zinc derivatives showed liquid crystalline behaviour at much higher temperatures than the metal-free compounds. The metal-free and zinc phthalocyanines with C12 chains had the lowest crystalline to discotic liquid crystalline mesophase transition temperatures. Variable temperature UV-VIS spectra of thin films (ca. 1000 Å thick) of the title compounds cast on glass were obtained for the compounds in the crystalline, meso- and isotropic liquid phase. The spectrum of a thin film of the isotropic liquid resembled the spectrum obtained from a solution of the same compound.

  一系列长链（C10、C12、C15 和 C18）3,6-二烷基邻苯二甲酰亚胺经 4 个步骤由噻吩制备而成，并转化为标题酞菁的无金属锌衍生物。使用 1H NMR、MALDI-TOF ms 和溶液相电子（UV-VIS）光谱对对称大环进行了表征。在二氯甲烷或 1,2-二氯乙烷中，拥有较短烷基取代基的无金属大环的四个环基氧化还原过程的电位范围为-1.8 至 1.2 V vs. Ag/Ag+。随着 8 个烷基取代基链长的增加，可逆性变差。锌配合物的氧化还原过程不像无金属酞菁那样明确。所有化合物都表现出盘状热向性液晶行为，研究采用了偏光光学显微镜和差示扫描量热法（DSC）。最多可检测到三种不同的介相。与不含金属的化合物相比，锌衍生物在更高的温度下显示出液晶特性。无金属酞菁和带有 C12 链的锌酞菁的结晶到盘状液晶介相转变温度最低。在玻璃上浇铸的薄膜（厚度约为 1000 埃）的变温紫外-可见光谱中，获得了结晶、介相和各向同性液相化合物的光谱。各向同性液态薄膜的光谱与同一化合物溶液的光谱相似。