5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene | 1398689-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene
• 英文别名: 5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-bis(triisopropylsilyl)naphtho-[1,2-b:5,6-b']dithiophene；5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b']dithiophene；NDT3-TIPS-Bpin；[5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-tri(propan-2-yl)silyl-[1]benzothiolo[7,6-g][1]benzothiol-7-yl]-tri(propan-2-yl)silane
• CAS: 1398689-49-0
• 化学式: C₄₄H₇₀B₂O₄S₂Si₂
• 分子量: 804.962
• InChiKey: QHOCRYLWWMCFSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.64
• 重原子数：
  54
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene 在 正丁基锂 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 正己烷 、 水 为溶剂， 反应 31.5h， 生成 5,10-bis(methoxycarbonyl)-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation

  摘要：

  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.

  DOI：

  10.1021/ol301797g
• 作为产物：
  描述：

  2,6-萘二酚 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 磺酰氯 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 sodium sulfide nonahydrate 、 溶剂黄146 、 三乙胺 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 82.0h， 生成 5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene
  参考文献：
  名称：

  유기 화합물과 이를 이용한 발광다이오드 및 유기발광다이오드 표시장치

  摘要：

  本发明具有在那非托[1,2-b:5,6-b']二硫杂苯核上具有取代电子吸引基团结构的有机化合物，提供了优秀的载流子注入特性和电荷生成特性。

  公开号：

  KR20160083235A

文献信息

• Contrasting Effect of Alkylation on the Ordering Structure in Isomeric Naphthodithiophene-Based Polymers
  作者：Itaru Osaka、Yoshinobu Houchin、Masayuki Yamashita、Takeshi Kakara、Noriko Takemura、Tomoyuki Koganezawa、Kazuo Takimiya

  DOI：10.1021/ma402518d

  日期：2014.5.27

  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.
• Naphtho[1,2-b:5,6-<i>b</i>′]dithiophene Based Two-Dimensional Conjugated Polymers for Highly Efficient Thick-Film Inverted Polymer Solar Cells
  作者：Xiangwei Zhu、Jin Fang、Kun Lu、Jianqi Zhang、Lingyun Zhu、Yifan Zhao、Zhigang Shuai、Zhixiang Wei

  DOI：10.1021/cm5033223

  日期：2014.12.23

  Two-dimensional conjugated zigzag naphthodithiophene was used for construction of novel polymer photovoltaic materials. Two novel copolymers based on zigzag naphthodithiophene and alkylthieno[3,4-c]pyrrole-4,6-dione inserted with different alkyl substituted thiophene as bridges have been designed and synthesized (PzNDTT-TPD1 and PzNDTT-TPD2, respectively). The best power conversion efficiency of a PzNDTT-TPD1-based device reaches 7.50% at an active layer thickness of 203 nm and the device performances of PzNDTT-TPD1-based polymer solar cells are all above 6.4% with active layer thickness variations from 141 to 244 nm, suggesting that it is very suitable for the fabrication of high performance, large area solution-processed polymer solar cells.
• EP2816044
  申请人：——

  公开号：——

  公开（公告）日：——