2,6-bis(3-dodecylthiophen-2-yl)benzo[1,2-d;4,5-d']bisthiazole | 1179520-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2,6-bis(3-dodecylthiophen-2-yl)benzo[1,2-d;4,5-d']bisthiazole
• 英文别名: 2,6-bis(3-dodecylthiophen-2-yl)-benzo[1,2-d:4,5'-d']bis[1,3]thiazole；2,6-Bis(3-dodecylthiophen-2-yl)-[1,3]thiazolo[5,4-f][1,3]benzothiazole
• CAS: 1179520-30-9
• 化学式: C₄₀H₅₆N₂S₄
• 分子量: 693.162
• InChiKey: LCTWHNZOAKTFBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18
• 重原子数：
  46
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-bis(3-dodecylthiophen-2-yl)benzo[1,2-d;4,5-d']bisthiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以69%的产率得到2,6-bis(5-bromo-3-dodecylthiophen-2-yl)benzo[1,2-d;4,5-d']bisthiazole
  参考文献：
  名称：

  Benzobisthiazole-Based Donor–Acceptor Copolymer Semiconductors for Photovoltaic Cells and Highly Stable Field-Effect Transistors

  摘要：

  Six new donor-acceptor copolymers based on benzobisthiazole and various donor moieties (dithienosilole, dithienopyrrole, cyclopentadithiophene, carbazole, benzodithiophene, and bithiophene) were synthesized, characterized, and used in field-effect transistors and solar cells. The series of polybenzobisthiazoles with donor acceptor architecture have optical band gaps of 1.83-2.18 eV, have identical LUMO energy levels (similar to-3.3 eV), and have a HOMO energy level that varied from -4.79 eV in PBTDTP to -5.71 eV in PBTHDDT. X-ray diffraction of the polybenzobisthiazole films showed a lamellar crystalline structure with an interlayer d-spacing of 1.56 nm in PBTOT to 1.83 nm in PBTDTP and 2.12 nm in PBTHDDT and a short pi-stacking distance (0.353-0.378 nm). The highly crystalline nature of the polybenzobisthiazoles facilitated high field-effect carrier mobility (up to 0.011 cm(2)/(V s)), which remained very stable under ambient conditions for 2 years. Bulk heterojunction solar cells made from one of the benzobisthiazole-based copolymers gave a power conversion efficiency of up to 3.0% under 100 mW/cm(2) AM1.5 sunlight illumination in air.

  DOI：

  10.1021/ma201128x
• 作为产物：
  描述：

  3-dodecylthiophene-2-carbaldehyde 、 2,5-diamino-1,4-benzenedithiol dihydrochloride 在 磷酸二苯酯 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以9%的产率得到2,6-bis(3-dodecylthiophen-2-yl)benzo[1,2-d;4,5-d']bisthiazole
  参考文献：
  名称：

  Benzobisthiazole-Based Donor–Acceptor Copolymer Semiconductors for Photovoltaic Cells and Highly Stable Field-Effect Transistors

  摘要：

  Six new donor-acceptor copolymers based on benzobisthiazole and various donor moieties (dithienosilole, dithienopyrrole, cyclopentadithiophene, carbazole, benzodithiophene, and bithiophene) were synthesized, characterized, and used in field-effect transistors and solar cells. The series of polybenzobisthiazoles with donor acceptor architecture have optical band gaps of 1.83-2.18 eV, have identical LUMO energy levels (similar to-3.3 eV), and have a HOMO energy level that varied from -4.79 eV in PBTDTP to -5.71 eV in PBTHDDT. X-ray diffraction of the polybenzobisthiazole films showed a lamellar crystalline structure with an interlayer d-spacing of 1.56 nm in PBTOT to 1.83 nm in PBTDTP and 2.12 nm in PBTHDDT and a short pi-stacking distance (0.353-0.378 nm). The highly crystalline nature of the polybenzobisthiazoles facilitated high field-effect carrier mobility (up to 0.011 cm(2)/(V s)), which remained very stable under ambient conditions for 2 years. Bulk heterojunction solar cells made from one of the benzobisthiazole-based copolymers gave a power conversion efficiency of up to 3.0% under 100 mW/cm(2) AM1.5 sunlight illumination in air.

  DOI：

  10.1021/ma201128x

文献信息

• Benzobisthiazole compound, benzobisthiazole polymer, organic film including the compound or polymer and transistor including the organic film
  申请人：Ricoh Company, Ltd.

  公开号：EP2085401B1

  公开（公告）日：2014-07-30
• BENZOBISTHIAZOLE COMPOUND, BENZOBISTHIAZOLE POLYMER, ORGANIC FILM INCLUDING THE COMPOUND OR POLYMER AND TRANSISTOR INCLUDING THE ORGANIC FILM
  申请人：Yamamoto Satoshi

  公开号：US20090230386A1

  公开（公告）日：2009-09-17

  A benzobisthiazole compound having a specific formula, and a benzobisthiazole polymer having a specific benzothiazole structure. An organic film including the benzobisthiazole polymer, the benzobisthiazole compound and/or a polymer obtained from the benzobisthiazole compound. An organic thin-film transistor including an organic semiconductor layer including the organic film; a pair of electrodes configured to flow an electric current through the organic semiconductor layer; and a third electrode configured to apply a voltage to the organic semiconductor layer.
• US8193304B2
  申请人：——

  公开号：US8193304B2

  公开（公告）日：2012-06-05
• Benzobisthiazole-Based Donor–Acceptor Copolymer Semiconductors for Photovoltaic Cells and Highly Stable Field-Effect Transistors
  作者：Eilaf Ahmed、Selvam Subramaniyan、Felix S. Kim、Hao Xin、Samson A. Jenekhe

  DOI：10.1021/ma201128x

  日期：2011.9.27

  Six new donor-acceptor copolymers based on benzobisthiazole and various donor moieties (dithienosilole, dithienopyrrole, cyclopentadithiophene, carbazole, benzodithiophene, and bithiophene) were synthesized, characterized, and used in field-effect transistors and solar cells. The series of polybenzobisthiazoles with donor acceptor architecture have optical band gaps of 1.83-2.18 eV, have identical LUMO energy levels (similar to-3.3 eV), and have a HOMO energy level that varied from -4.79 eV in PBTDTP to -5.71 eV in PBTHDDT. X-ray diffraction of the polybenzobisthiazole films showed a lamellar crystalline structure with an interlayer d-spacing of 1.56 nm in PBTOT to 1.83 nm in PBTDTP and 2.12 nm in PBTHDDT and a short pi-stacking distance (0.353-0.378 nm). The highly crystalline nature of the polybenzobisthiazoles facilitated high field-effect carrier mobility (up to 0.011 cm(2)/(V s)), which remained very stable under ambient conditions for 2 years. Bulk heterojunction solar cells made from one of the benzobisthiazole-based copolymers gave a power conversion efficiency of up to 3.0% under 100 mW/cm(2) AM1.5 sunlight illumination in air.