5,10-dibromo-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene | 1398689-50-3

• 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-dibromo-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene
• 英文别名: 5,10-dibromo-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b']dithiophene；[5,10-Dibromo-2-tri(propan-2-yl)silyl-[1]benzothiolo[7,6-g][1]benzothiol-7-yl]-tri(propan-2-yl)silane
• CAS: 1398689-50-3
• 化学式: C₃₂H₄₆Br₂S₂Si₂
• 分子量: 710.828
• InChiKey: RDJMGOLIULDXGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.57
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 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-dibromo-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 15.5h， 生成 α-DTTNAP
  参考文献：
  名称：

  Dithiophene-Fused Tetracyanonaphthoquinodimethanes (DT-TNAPs): Synthesis and Characterization of π-Extended Quinoidal Compounds for n-Channel Organic Semiconductor

  摘要：

  Dithiophene-fused tetracyanonaphthoquinodimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (similar to 4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, alpha-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10(-3) cm(-2) V-1 s(-1), indicating that DTTNAPs are a potential molecular framework for channel organic semiconductors.

  DOI：

  10.1021/ol403234q
• 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 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 正己烷 、 二氯甲烷 、 环己烷 、 水 为溶剂， 反应 97.0h， 生成 5,10-dibromo-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.
• EP2816044
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Quinoidal Naphtho[1,2-<i>b</i>:5,6-<i>b</i>′]dithiophenes for Solution-Processed n-Channel Organic Field-Effect Transistors
  作者：Takamichi Mori、Naoyuki Yanai、Itaru Osaka、Kazuo Takimiya

  DOI：10.1021/ol5000567

  日期：2014.3.7

  A series of new quinoidal naphthodithiophenes, 2,7-bis(alpha,alpha-dicyanomethylene)-2,7-dihydronaphtho[1,2-b:5,6-b']dithiophenes, in which all the four fused aromatic rings are incorporated into the quinoidal system, were synthesized and evaluated as an n-channel organic semiconductor. Solution-processed field-effect transistors exhibited typical n-channel transistor characteristics with the mobility as high as 0.1 cm(2) V-1 s(-1), which is higher by more than I order of magnitude than those reported for isomeric quinoidal naphthodithiophenes having a naphthoquinoidal structure.
• Naphthodithiophene–Naphthobisthiadiazole Copolymers for Solar Cells: Alkylation Drives the Polymer Backbone Flat and Promotes Efficiency
  作者：Itaru Osaka、Takeshi Kakara、Noriko Takemura、Tomoyuki Koganezawa、Kazuo Takimiya

  DOI：10.1021/ja404064m

  日期：2013.6.19

  We show that rational functionalization of the naphthodithiophene core in copolymers based on naphthodithiophene and naphthobisthiadiazole improves the solubility without an alteration of the electronic structure. Surprisingly, the introduction of linear alkyl chains brings about a drastic change in polymer orientation into the face-on motif, which is beneficial for the charge transport in solar cells. As a result, the present polymers exhibit high power conversion efficiencies of up to similar to 8.2% in conventional single-junction solar cells.