2,6-diphenylbenzo[1,2-b:4,5-b']dithiophene | 219597-02-1

• 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: 2,6-diphenylbenzo[1,2-b:4,5-b']dithiophene
• 英文别名: 2,6-diphenylthieno[2,3-f][1]benzothiole
• CAS: 219597-02-1
• 化学式: C₂₂H₁₄S₂
• 分子量: 342.485
• InChiKey: WNNUVWFCGFUJFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  2,5-二(苯乙炔基)-1,4-二溴苯 在 sodiumsulfide nonahydrate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 12.0h， 以57%的产率得到2,6-diphenylbenzo[1,2-b:4,5-b']dithiophene
  参考文献：
  名称：

  一锅合成邻位卤代乙炔苯合成苯并[ b ]噻吩和苯并[ b ]硒代苯：单，双和三硫代青冈烯取代的苯的简便方法

  摘要：

  描述了一种方便的一锅法，用于从容易获得的邻卤代乙炔基苯前体合成苯并[ b ]噻吩和硒代苯。不论乙炔末端上的取代基或前体上的环化部分数量如何，各种苯并[ b ]噻吩和硒代苯不仅包括母体，烷基和苯基取代的衍生物，而且还包括苯并[1,2- b]可以高产率地制备： 4，5- b ′]二噻吩和二硒吩和苯并[1，2- b： 3，4- b ′：5，6 - b ′′]三噻吩和三硒吩。

  DOI：

  10.1021/ol900809w

文献信息

• Nickel-catalyzed and Li-mediated regiospecific C–H arylation of benzothiophenes
  作者：Yorck Mohr、Gaëlle Hisler、Léonie Grousset、Yoann Roux、Elsje Alessandra Quadrelli、Florian M. Wisser、Jérôme Canivet

  DOI：10.1039/d0gc00917b

  日期：——

  A nickel-based catalytic system for the regiospecific C2–H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles

  建立了用于苯并噻吩的区域特异性C2-H芳基化的镍基催化体系。NiCl 2（bpy）与LiHMDS作为二恶烷中的碱结合使用。该催化体系适用于各种功能化的苯并噻吩，以及其他杂芳烃，包括噻吩，苯并二噻吩，苯并呋喃和硒烯与碘代芳基亲电试剂的组合。讨论了LiHMDS作为独特有效基础和假定机制的作用。最终证明了该系统对合成活性药物成分中间体的适用性。
• NOVEL COMPOUND AND ORGANIC SEMICONDUCTOR MATERIAL
  申请人：Miyata Yasuo

  公开号：US20110166362A1

  公开（公告）日：2011-07-07

  Discloses is a compound represented by the formula (1): wherein a ring structure A and a ring structure B independently represent an aromatic ring which may be substituted, or a heterocyclic ring which may be substituted; a ring structure C represents a benzene ring which may be substituted, a hetero[3,2-b]heterole ring, or a benzo[1,2-b:4,5-b′]diheterole ring which may be substituted; W, X, Y and Z independently represent a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, SO 2 , (R 1 )—C—(R 2 ), (R 2 )—Si—(R 4 ), or N—(R 5 ), and at least one of W, X, Y and Z is N—(R 5 ); R 1 , R 2 , R 3 , R 4 and R 5 independently represent a hydrogen atom, a substituent i, a substituent ii, an aryl group which may be substituted with halogen, or a heteroaryl group which may be substituted with halogen, the substituent i is a group selected from Group P shown below, the substituent ii is a group selected from Group P shown below which group is substituted, and Group P consists of an alkyl group, an alkoxy group, an alkyl-substituted aryl group, an alkoxy-substituted aryl group, and an alkyl-substituted heteroaryl group.

  Discloses是一种由公式（1）表示的化合物： 其中，环结构A和环结构B分别表示可以被取代的芳香环或杂环；环结构C表示可以被取代的苯环、杂[3,2-b]杂环或可以被取代的苯并[1,2-b:4,5-b′]二杂环；W，X，Y和Z分别表示硫原子、氧原子、硒原子、碲原子、SO2、(R1)-C-(R2)、(R2)-Si-(R4)或N-(R5)，并且W，X，Y和Z中至少有一个是N-(R5)；R1，R2，R3，R4和R5分别表示氢原子、取代基i、取代基ii、可以被卤素取代的芳基或可以被卤素取代的杂芳基，其中取代基i是从下面所示的P组中选择的一组取代基，取代基ii是从下面所示的P组中选择的一组取代基，该组取代基被取代，P组包括烷基、烷氧基、烷基取代的芳基、烷氧基取代的芳基和烷基取代的杂芳基。
• FIELD EFFECT TRANSISTOR
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP2207218A1

  公开（公告）日：2010-07-14

  Disclosed is a field effect transistor which has a practical carrier mobility, low threshold voltage and low energy consumption by using a specific organic compound as a semiconductor material. Specifically disclosed is a field effect transistor which is characterized in that a semiconductor layer is formed by using at least one compound represented by Formula (1) below as a semiconductor material. wherein, X1 and X2 independently represent a sulfur atom, a selenium atom or a tellurium atom; and R1 and R2 independently represent a C1-C14 alkyl group. When both X1 and X2 are selenium atoms, R1 and R2 independently represent a C1-C4 alkyl group.

  本发明公开了一种场效应晶体管，该晶体管使用特定的有机化合物作为半导体材料，具有实用的载流子迁移率、低阈值电压和低能耗。具体地说，本发明公开了一种场效应晶体管，其特征在于通过使用至少一种由下式（1）表示的化合物作为半导体材料形成半导体层。 其中，X1 和 X2 独立地代表硫原子、硒原子或碲原子；R1 和 R2 独立地代表 C1-C14 烷基。当 X1 和 X2 均为硒原子时，R1 和 R2 独立地代表 C1-C4 烷基。
• Method for producing benzo-trithiophene or benzo-triselenophene derivatives
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP2371829A1

  公开（公告）日：2011-10-05

  Disclosed is a method for producing an aromatic compound represented by the general formula (6') below, which is characterized in that a compound represented by the general formula (6) below is reacted with a sulfur compound (at least one member selected from the group consisting of sulfur, hydrogen sulfide, metal hydrosulfides and metal sulfides) or a selenium compound. (In the formula (6), R1 represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an ester group, an optionally substituted alkyl group having 1-18 carbon atoms or the like; R2 represents a halogen atom; (In the formula (6'), R1 is as defined in the formula (6); and X represents a sulfur atom or a selenium atom.)

  本发明公开了一种生产由以下通式(6')表示的芳香族化合物的方法，其特征在于由以下通式(6)表示的化合物与硫化合物(至少一种选自由硫、硫化氢、金属氢硫化物和金属硫化物组成的组)或硒化合物反应。(在式 (6) 中，R1 代表氢原子、卤素原子、羟基、氰基、硝基、酯基、具有 1-18 个碳原子的任选取代烷基或类似基团；R2 代表卤素原子；（在式 (6') 中，R1 如式 (6) 所定义；X 代表硫原子或硒原子）。
• 2,6-Diphenylbenzo[1,2-<i>b</i>:4,5-<i>b</i>‘]dichalcogenophenes:  A New Class of High-Performance Semiconductors for Organic Field-Effect Transistors
  作者：Kazuo Takimiya、Yoshihito Kunugi、Yasushi Konda、Naoto Niihara、Tetsuo Otsubo

  DOI：10.1021/ja0496930

  日期：2004.4.28

  2,6-Diphenylbenzo[1,2-b:4,5-b']dichalcogenophenes including thiophene, selenophene, and tellurophene analogues as organic semiconductors for field-effect transistors were effectively synthesized in three steps from commercially available 1,4-dibromobenzene. All three benzodichalcogenophenes acted as good p-type semiconductors, and particularly the selenophene analogue, 2,6-diphenylbenzo[1,2-b:4,5-b']diselenophene, showed high FET mobility of 0.17 cm2 V-1 s-1.