hexakis[2,2-bis(butoxymethyl)-1,3-propanediyl]dodecithiophene | 957796-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: hexakis[2,2-bis(butoxymethyl)-1,3-propanediyl]dodecithiophene
• 英文别名: 1-[1-[5,5-Bis(butoxymethyl)-1-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]-4,6-dihydrocyclopenta[c]thiophen-3-yl]-5,5-bis(butoxymethyl)-4,6-dihydrocyclopenta[c]thiophen-3-yl]-3-[1-[1-[5,5-bis(butoxymethyl)-1-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]-4,6-dihydrocyclopenta[c]thiophen-3-yl]-5,5-bis(butoxymethyl)-4,6-dihydrocyclopenta[c]thiophen-3-yl]-5,5-bis(butoxymethyl)-4,6-dihydrocyclopenta[c]thiophen-3-yl]-5,5-bis(butoxymethyl)-4,6-dihydrocyclopenta[c]thiophene；1-[1-[5,5-bis(butoxymethyl)-1-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]-4,6-dihydrocyclopenta[c]thiophen-3-yl]-5,5-bis(butoxymethyl)-4,6-dihydrocyclopenta[c]thiophen-3-yl]-3-[1-[1-[5,5-bis(butoxymethyl)-1-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]-4,6-dihydrocyclopenta[c]thiophen-3-yl]-5,5-bis(butoxymethyl)-4,6-dihydrocyclopenta[c]thiophen-3-yl]-5,5-bis(butoxymethyl)-4,6-dihydrocyclopenta[c]thiophen-3-yl]-5,5-bis(butoxymethyl)-4,6-dihydrocyclopenta[c]thiophene
• CAS: 957796-99-5
• 化学式: C₁₂₆H₁₇₀O₁₂S₁₂
• 分子量: 2261.52
• InChiKey: RYIVRLGQNZISIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  32.5
• 重原子数：
  150
• 可旋转键数：
  71
• 环数：
  18.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  450
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  5,5'''''-dibromo-3,4:3',4':3'',4'':3''',4''':3'''',4'''':3''''',4'''''-hexakis[2,2-bis(butoxymethyl)-1,3-propanediyl]sexithiophene 、 2-tri(n-butyl)stannylterthiophene 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以51%的产率得到hexakis[2,2-bis(butoxymethyl)-1,3-propanediyl]dodecithiophene
  参考文献：
  名称：

  Conductive, Magnetic, and Optical Properties of Sterically Hindered Dodecithiophenes. Evidence for the Coexistence of Bipolaron and π-Dimer

  摘要：

  对带有大体积2,2-双(丁氧基甲基)-1,3-丙二基的立体阻碍十二硫吩的电导率、磁性和光学性质进行了研究。在用FeCl3高掺杂时，完全阻碍的十二硫吩的电导率仅为5×10−4 S cm−1，但两种部分阻碍的十二硫吩的电导率相对较高，分别为1.9和0.6 S cm−1，比未阻碍的十二硫吩的电导率（38 S cm−1）低一到两个数量级。尽管这些十二硫吩的结构和电导率不同，但所有掺杂的固体均不具有磁性，并且在近红外区域显示出类似的光吸收光谱，这与聚噻吩的一般观察结果一致。另一方面，它们在二氯甲烷中的光谱彼此差异很大。高掺杂下未阻碍的十二硫吩的溶液光谱的特征是两个可归因于π-二聚体的吸收跃迁。另一方面，完全阻碍的十二硫吩的溶液光谱的特征是双极子引起的吸收跃迁。此外，两种部分阻碍的十二硫吩的溶液光谱可以解释为π-二聚体和双极子带重叠的结果。从这些结果来看，π-二聚体和双极子似乎都可以作为导电聚（寡）噻吩中的活性电荷载体。

  DOI：

  10.1246/bcsj.80.1799

文献信息

• Conductive, Magnetic, and Optical Properties of Sterically Hindered Dodecithiophenes. Evidence for the Coexistence of Bipolaron and π-Dimer
  作者：Tomoyuki Kurata、Takashi Mohri、Kazuo Takimiya、Tetsuo Otsubo

  DOI：10.1246/bcsj.80.1799

  日期：2007.9.15

  Conductive, magnetic, and optical properties of sterically hindered dodecithiophenes bearing bulky 2,2-bis(butoxymethyl)-1,3-propanediyl groups were examined. At high doping with FeCl3, a completely hindered dodecithiophene had only a poor conductivity of 5×10−4 S cm−1, but two partially hindered dodecithiophenes had relatively high conductivities of 1.9 and 0.6 S cm−1, which are one or two orders lower than the conductivity (38 S cm−1) of the unhindered dodecithiophene. Despite having different structures and conductivities, all of the doped solids of these dodecithiophenes were magnetically inactive and demonstrated similar optical absorption spectra in the near infrared region, as generally observed for polythiophenes. On the other hand, their optical spectra in dichloromethane were quite different from one another. A solution spectrum of the unhindered dodecithiophene under high doping was characterized by two absorption transitions assignable to a π-dimer. On the other hand, a solution spectrum of the completely hindered dodecithiophene was characterized by an absorption transition due to a bipolaron. Furthermore, the solution spectra of two partially hindered dodecithiophenes could be explained as an overlap of both π-dimeric and bipolaronic bands. From these results, both π-dimer and bipolaron species appear to serve as active charge carriers in conductive poly(oligo)thiophenes.

  对带有大体积2,2-双(丁氧基甲基)-1,3-丙二基的立体阻碍十二硫吩的电导率、磁性和光学性质进行了研究。在用FeCl3高掺杂时，完全阻碍的十二硫吩的电导率仅为5×10−4 S cm−1，但两种部分阻碍的十二硫吩的电导率相对较高，分别为1.9和0.6 S cm−1，比未阻碍的十二硫吩的电导率（38 S cm−1）低一到两个数量级。尽管这些十二硫吩的结构和电导率不同，但所有掺杂的固体均不具有磁性，并且在近红外区域显示出类似的光吸收光谱，这与聚噻吩的一般观察结果一致。另一方面，它们在二氯甲烷中的光谱彼此差异很大。高掺杂下未阻碍的十二硫吩的溶液光谱的特征是两个可归因于π-二聚体的吸收跃迁。另一方面，完全阻碍的十二硫吩的溶液光谱的特征是双极子引起的吸收跃迁。此外，两种部分阻碍的十二硫吩的溶液光谱可以解释为π-二聚体和双极子带重叠的结果。从这些结果来看，π-二聚体和双极子似乎都可以作为导电聚（寡）噻吩中的活性电荷载体。