2-phenylthieno[3,4-b]thiophene | 204654-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-phenylthieno[3,4-b]thiophene
• 英文别名: 2-phenylthieno[2,3-c]thiophene
• CAS: 204654-26-2
• 化学式: C₁₂H₈S₂
• 分子量: 216.328
• InChiKey: VCEQRJWBUJIROQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• 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

反应信息

• 作为产物：
  描述：

  3-bromo-4-(phenylethynyl)thiophene 在 sodium sulfide 、 copper(II) oxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以22%的产率得到2-phenylthieno[3,4-b]thiophene
  参考文献：
  名称：

  Thieno[3,4-b]thiophene Acceptors with Alkyl, Aryl, Perfluoroalkyl, and Perfluorophenyl Pendants for Donor–Acceptor Low Bandgap Polymers

  摘要：

  We report the design, synthesis, and characterization of a series of thieno[3,4-b]thiophene acceptor blocks with octyl (T8), phenyl (TP), perfluorooctyl (TF8), and perfluorophenyl (TFP) side groups. Their subsequent copolymerization with dithienylbenzodithiophene by direct arylation polymerization afforded novel low bandgap poly(thienothiophene-alt-dithienylbenzodithiophene) (PTB) polymers. The strongly electron with-drawing TF8 and TFP groups were shown to significantly lower both E-HOMO and E-LUMO levels and gave computed copolymer ground-to-excited state dipole changes (triangle mu(ge)) that were relatively higher than for the nonfluorinated analogues. These materials show favorably aligned energy levels relative to conventional fullerene-type acceptors, which should allow them to perform well in organic photovoltaics.

  DOI：

  10.1021/ma4019476

文献信息

• Heterocyclic Fused Isothiazole and Isoselenazole Monomers and Conducting Polymers
  申请人：Zahn Steffen

  公开号：US20070238854A1

  公开（公告）日：2007-10-11

  A composition of matter having the following structure: where X is S or Se; and Y is NH, O, S, or Se; and R is an H, a C 1-8 F 3-17 primary, secondary, or tertiary fluoroalkyl, a C 1-20 primary, secondary or tertiary alkyl, or a halogen atom, and a composition of matter comprising polymerized units having the following structure: where X is S or Se; and Y is NH, O, S, or Se; and R is an H, a C 1-8 F 3-17 primary, secondary, or tertiary fluoroalkyl, a C 1-20 primary, secondary or tertiary alkyl, or a halogen atom.

  具有以下结构的物质组成：其中X为S或Se；而Y为NH、O、S或Se；而R为H、C1-8F3-17一级、二级或三级氟烷基、C1-20一级、二级或三级烷基或卤素原子。具有以下结构的聚合单元组成的物质：其中X为S或Se；而Y为NH、O、S或Se；而R为H、C1-8F3-17一级、二级或三级氟烷基、C1-20一级、二级或三级烷基或卤素原子。
• PENTAFLUOROSULFANYL-SUBSTITUTED THIENOTHIOPHENE MONOMERS AND CONDUCTING POLYMERS
  申请人：Zahn Steffen

  公开号：US20060074250A1

  公开（公告）日：2006-04-06

  Thienothiophene monomers having an SF 5 group and conducting oligomers and polymers formed by the polymerization of such monomers and their use as hole injection materials, charge transport materials, or as semiconductors. The compound may be of the formula: where X and X′ are independently H, halogen atoms (e.g., F, Cl, Br, and I), MgCl, MgBr, MgI, Sn(R′) 3 , where R′ comprises C 1-6 alkyl or —OC 1-6 alkyl, boronic acid, boronic ester, —CH═CHR″ (where R″ comprises H or C 1-6 alkyl), —OC 1-6 alkyl, —COOC 1-6 alkyl, —S—COR″′ and —COR″′ (where R″′ comprises H or C 1-6 alkyl), —C≡CH, or polymerizable aromatic rings (such as phenyl, naphthalene, pyrrole, dithiophene, thienothiophene, thiophene and so forth).

  具有SF5基团的噻吩单体和由这些单体聚合形成的导电寡聚物和聚合物，以及它们作为空穴注入材料、电荷传输材料或半导体的用途。该化合物可以是以下公式：其中X和X′独立地为H、卤素原子（例如F、Cl、Br和I）、MgCl、MgBr、MgI、Sn（R′）3，其中R′包括C1-6烷基或—OC1-6烷基、硼酸、硼酸酯、—CH═CHR″（其中R″为H或C1-6烷基）、—OC1-6烷基、—COOC1-6烷基、—S—COR″′和—COR″′（其中R″′为H或C1-6烷基）、—C≡CH或可聚合芳香环（例如苯、萘、吡咯、二噻吩、噻吩等）。
• Fluorinated alkyl substituted-thieno[3,4-b]thiophene monomers and polymers therefrom
  申请人：Zahn Steffen

  公开号：US20050209419A1

  公开（公告）日：2005-09-22

  Partially and fully fluorinated alkyl substituted thienothiophene monomers (and polymers thereof) wherein the monomers are represented by the formula: wherein R is a partially or fully fluorinated primary, secondary or tertiary alkyl having from 1 to 8 carbon atoms; and X and X′ are independently selected from the group consisting of H, F, Cl, Br, I, MgCl, MgBr, Mgl, Sn(R′) 3 , CH═CHR″, —OR″, —COOR″, —S—COR″, —B(OR″) 2 , —COR″, —C≡CH, and a polymerizable cyclic pi-conjugated carbon-ring structure optionally comprising S, N or O heteroatoms; wherein R′ is a primary, secondary or tertiary alkyl having from 1 to 6 carbon atoms, and R″ is H or a primary, secondary or tertiary alkyl having from 1 to 6 carbon atoms.

  部分或完全氟代烷基取代的噻吩二噻吩单体（及其聚合物），其中单体由以下公式表示： 其中，R是部分或完全氟代的一级、二级或三级烷基，其碳原子数为1至8；X和X'分别选自H、F、Cl、Br、I、MgCl、MgBr、Mgl、Sn（R'）3、CH═CHR"、—OR"、—COOR"、—S—COR"、—B（OR"）2、—COR"、—C≡CH和可选包含S、N或O杂原子的可聚合环状pi-共轭碳环结构；其中，R'是一级、二级或三级烷基，其碳原子数为1至6，R"是H或一级、二级或三级烷基，其碳原子数为1至6。
• Pentafluorosulfanyl-substituted thienothiophene monomers and conducting polymers
  申请人：AIR PRODUCTS AND CHEMICALS, INC.

  公开号：EP1642896A1

  公开（公告）日：2006-04-05

  Thienothiophene monomers having an SF5 group and conducting oligomers and polymers formed by the polymerization of such monomers and their use as hole injection materials, charge transport materials, or as semiconductors. The compound may be of the formula: where X and X' are independently H, halogen atoms (e.g., F, Cl, Br, and I), MgCl, MgBr, Mgl, Sn(R')3, where R' comprises C1-6 alkyl or -OC1-6 alkyl, boronic acid, boronic ester, - CH=CHR" (where R" comprises H or C1-6 alkyl), -OC1-6 alkyl, -COOC1-6 alkyl, -S-COR"' and -COR''' (where R''' comprises H or C1-6 alkyl), -C≡CH, or polymerizable aromatic rings (such as phenyl, naphthalene, pyrrole, dithiophene, thienothiophene, thiophene and so forth).

  具有 SF5 基团的噻吩单体和由此类单体聚合形成的导电低聚物和聚合物，以及它们作为空穴注入材料、电荷传输材料或半导体的用途。该化合物的化学式如下 其中 X 和 X' 独立地为 H、卤素原子（如：F、Cl、Br 和 I）、F、Cl、Br 和 I）、MgCl、MgBr、Mgl、Sn(R')3（其中 R'包括 C1-6 烷基或-OC1-6 烷基）、硼酸、硼酸酯、-CH=CHR"（其中 R "包括 H 或 C1-6 烷基）、-OC1-6 烷基、-COOC1-6 烷基、-S-COR"'和-COR'''（其中 R'''包括 H 或 C1-6 烷基）、-C≡CH 或可聚合芳环（如苯基、萘、吡咯、二噻吩、噻吩、噻吩等）。
• Selenium containing electrically conductive polymers and method of making them
  申请人：Air Products and Chemicals, Inc.

  公开号：EP2014665A2

  公开（公告）日：2009-01-14

  Monomeric, oligomeric and polymeric electrically conductive compounds and methods of making the compounds having a repeating unit having formula P1, as follows: where X is S or Se, Y is S or Se, wherein one or both of X and Y is Se, R is a substituent group capable of bonding to the ring structure. R may include hydrogen or isotopes thereof, hydroxyl, alkyl, including C1 to C20 primary, secondary or tertiary alkyl groups, arylalkyl, alkenyl, perfluoroalkyl, perfluororaryl, aryl, alkoxy, cycloalkyl, cycloalkenyl, alkanoyl, alkylthio, aryloxy, alkylthioalkyl, alkynyl, alkylaryl, arylalkyl, amido, alkylsulfinyl, alkoxyalkyl, alkylsulfonyl, aryl, arylamino, diarylamino, alkylamino, dialkylamino, arylarylamino, arylthio, heteroaryl, arylsulfinyl, alkoxycarbonyl, arylsulfonyl, carboxyl, halogen, nitro, cyano, sulfonic acid, or alkyl or phenyl substituted with one or more sulfonic acid, phosphoric acid, carboxylic acid, halo, amino, nitro, hydroxyl, cyano or epoxy moieties. Electrical devices utilizing the electrically conductive polymers is also disclosed.

  单体、低聚物和聚合导电化合物以及制造这些化合物的方法，这些化合物具有如下式 P1 的重复单元： 其中 X 是 S 或 Se，Y 是 S 或 Se，其中 X 和 Y 中的一个或两个是 Se，R 是能与环结构键合的取代基。芳基、芳基氨基、二芳基氨基、烷基氨基、二烷基氨基、芳基芳基氨基、芳硫基、杂芳基、芳基亚磺酰基、烷氧基羰基、芳基磺酰基、羧基、卤素、硝基、氰基、磺酸或被一个或多个磺酸、磷酸、羧酸、卤素、氨基、硝基、羟基、氰基或环氧基取代的烷基或苯基。还公开了利用导电聚合物的电气设备。