2,7-dibromo-5,10-didodecylnaphtho[1,2-b:5,6-b']dithiophene | 1569744-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,7-dibromo-5,10-didodecylnaphtho[1,2-b:5,6-b']dithiophene
• 英文别名: 2,7-Dibromo-5,10-didodecyl-[1]benzothiolo[7,6-g][1]benzothiole
• CAS: 1569744-43-9
• 化学式: C₃₈H₅₄Br₂S₂
• 分子量: 734.787
• InChiKey: FATNNDNNXYADFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.7
• 重原子数：
  42
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  2,7-dibromo-5,10-didodecylnaphtho[1,2-b:5,6-b']dithiophene 在 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 17.0h， 生成 2-[2-(Dicyanomethylidene)-5,10-didodecyl-[1]benzothiolo[7,6-g][1]benzothiol-7-ylidene]propanedinitrile
  参考文献：
  名称：

  Quinoidal Naphtho[1,2-b:5,6-b′]dithiophenes for Solution-Processed n-Channel Organic Field-Effect Transistors

  摘要：

  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.

  DOI：

  10.1021/ol5000567
• 作为产物：
  描述：

  5,10-dibromo-2,7-bis(triisopropylsilyl)naphtho[1,2-b:5,6-b’]dithiophene 在 正丁基锂 、 四丁基氟化铵 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 31.0h， 生成 2,7-dibromo-5,10-didodecylnaphtho[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  Quinoidal Naphtho[1,2-b:5,6-b′]dithiophenes for Solution-Processed n-Channel Organic Field-Effect Transistors

  摘要：

  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.

  DOI：

  10.1021/ol5000567

文献信息

• Reversible Dimerization and Polymerization of a Janus Diradical To Produce Labile C−C Bonds and Large Chromic Effects
  作者：José L. Zafra、Lili Qiu、Naoyuki Yanai、Takamichi Mori、Masahiro Nakano、Miriam Peña Alvarez、Juan T. López Navarrete、Carlos J. Gómez‐García、Miklos Kertesz、Kazuo Takimiya、Juan Casado

  DOI：10.1002/anie.201605997

  日期：2016.11.14

  irreversible diradical monomer polymerization. A reversible version of this reaction consisting of the formation/dissociation of σ‐dimers and σ‐polymers from a stable quinonoidal diradical precursor is described. The reaction reversibility is made by a quinonoidal molecule which changes its structure to an aromatic species by forming weak and long intermolecular C−C single bonds. The reaction provokes

  导电聚合物可以通过不可逆的双自由基单体聚合反应合成。描述了此反应的可逆版本，其中包括从稳定的醌型双自由基前体形成/解离σ-二聚体和σ-聚合物。反应可逆性是由醌型分子产生的，该醌型分子通过形成弱而长的分子间CC单键将其结构改变为芳香族。该反应引起约2.5eV的巨大的铬效应。两种相对但互补的醌型和芳族互变异构体提供了产生所观察到的铬效应的反应物和产物的Janus面。提出了一种反应机理来解释从结构上非常相似的反应物开始的最终产物的种类。这些可逆反应
• NOVEL CONDENSED POLYCYCLIC AROMATIC COMPOUND AND USE THEREOF
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP2963042A1

  公开（公告）日：2016-01-06

  [Problem] To provide: a novel compound which has high mobility and on/off ratio and is useful for organic electronic devices; and a method for producing the compound. [Solution] A condensed polycyclic aromatic compound which is represented by general formula (1). (In the formula, A represents a 1,5-dihydronaphthalene ring or a 2,6-dihydronaphthalene ring; each of R1, R2, R3 and R4 independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alicyclic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted hydrocarbon oxy group, a substituted or unsubstituted ester group, a substituted or unsubstituted acyl group, or a substituted or unsubstituted cyano group; and each of X1 and X2 independently represents an oxygen atom, a sulfur atom or a selenium atom.)

  [问题]提供：一种新型化合物，它具有高迁移率和高开/关比，可用于有机电子设备； 以及生产该化合物的方法。[解决方案] 一种缩合多环芳烃化合物，由通式（1）表示。(式中，A 代表 1，5-二氢萘环或 2，6-二氢萘环；R1、R2、R3 和 R4 各自独立地代表氢原子、卤素原子、取代或未取代的脂肪烃基、取代或未取代的脂环烃基、取代或未取代的芳香烃基、取代或未取代的烃氧基、取代或未取代的酯基、取代或未取代的酰基或取代或未取代的氰基；X1和X2各自独立地代表氧原子、硫原子或硒原子。)
• Novel Condensed Polycyclic Aromatic Compound And Use Thereof
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US20160013428A1

  公开（公告）日：2016-01-14

  [Problem] To provide: a novel compound which has high mobility and on/off ratio and is useful for organic electronic devices; and a method for producing the compound. [Solution] A condensed polycyclic aromatic compound which is represented by general formula (1). (In the formula, A represents a 1,5-dihydronaphthalene ring or a 2,6-dihydronaphthalene ring; each of R 1 , R 2 , R 3 and R 4 independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alicyclic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted hydrocarbon oxy group, a substituted or unsubstituted ester group, a substituted or unsubstituted acyl group, or a substituted or unsubstituted cyano group; and each of X 1 and X 2 independently represents an oxygen atom, a sulfur atom or a selenium atom.)
• US9859508B2
  申请人：——

  公开号：US9859508B2

  公开（公告）日：2018-01-02