5,10-dihexadecyl-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene | 1398689-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,10-dihexadecyl-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene
• 英文别名: 5,10-dihexadecyl-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b']dithiophene；[5,10-Dihexadecyl-2-tri(propan-2-yl)silyl-[1]benzothiolo[7,6-g][1]benzothiol-7-yl]-tri(propan-2-yl)silane
• CAS: 1398689-54-7
• 化学式: C₆₄H₁₁₂S₂Si₂
• 分子量: 1001.9
• InChiKey: UAELYRKXPOCLOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.09
• 重原子数：
  68
• 可旋转键数：
  38
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,10-dihexadecyl-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2,7-bis(trimethylstannyl)-5,10-dihexadecylnaphtho[1,2-b:5,6-b’]dithiophene
  参考文献：
  名称：

  Contrasting Effect of Alkylation on the Ordering Structure in Isomeric Naphthodithiophene-Based Polymers

  摘要：

  Semiconducting polymers with alkylated naphtho[1,2-b:5,6-b']dithiophene (NDT3) and naphtho[2,1-b:6,5-b']dithiophene (NDT4) are synthesized and characterized. The solubility of the present polymers is significantly improved as compared to the nonalkylated counterparts with preserving the good charge transport properties. Interestingly, the effect of alkylation is found to be quite distinct between the NDT3 and NDT4 cores. In the NDT3-based polymers, alkylation leads to the more ordered backbone structure and thus the increased crystalline order in the thin film. On the other hand, in the NDT4-based polymers, alkylation is detriment to the backbone ordering, which gives rise to the face-on orientation or amorphous like film structure. This difference can be qualitatively explained by the different alkyl placement; all the neighboring alkyl groups are in the anti arrangement in the NDT3-based polymers, whereas the arrangement is a mixture of anti and syn in the NDT4-based polymers, which likely causes steric impact on the backbone. These observations make us better understood how the alkylation affect the ordering structures, which would be an important guideline for the design of superior semiconducting polymers.

  DOI：

  10.1021/ma402518d
• 作为产物：
  描述：

  2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b']dithiophene 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 9-硼双环[3.3.1]壬烷 、 4,4'-二叔丁基-2,2'-二吡啶 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 环己烷 、 水 为溶剂， 反应 46.0h， 生成 5,10-dihexadecyl-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene
  参考文献：
  名称：

  EP2816044

  摘要：

  公开号：

文献信息

• Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation
  作者：Shoji Shinamura、Ryusuke Sugimoto、Naoyuki Yanai、Noriko Takemura、Tomoya Kashiki、Itaru Osaka、Eigo Miyazaki、Kazuo Takimiya

  DOI：10.1021/ol301797g

  日期：2012.9.21

  Selective functionalization protocols of naphtho[1,2-b;5,6-b']dithiophene (NDT3) by combining protection of the thiophene alpha-positions and direct borylation on the naphthalene core are described, which allows synthesizing a number of new NDT3-based building blocks with various substituents and isomeric NDT3-based polymers with different main chain structures. The same protocol is applicable to other isomeric naphthodithiophenes (NDTs), which affords a set of key building blocks for the development of elaborated functional pi-materials.