2,5-bis(5-bromo-3-octyloxy-thiophen-2-yl)-thiazolo[5,4-d]thiazole | 1294515-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,5-bis(5-bromo-3-octyloxy-thiophen-2-yl)-thiazolo[5,4-d]thiazole
• 英文别名: 2,5-Bis(5-bromo-3-octoxythiophen-2-yl)-[1,3]thiazolo[5,4-d][1,3]thiazole
• CAS: 1294515-52-8
• 化学式: C₂₈H₃₆Br₂N₂O₂S₄
• 分子量: 720.678
• InChiKey: YVQMWUNZEQOQGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  38
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-bis(5-bromo-3-octyloxy-thiophen-2-yl)-thiazolo[5,4-d]thiazole 、 三甲基氯化锡 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以82%的产率得到2,5-bis(3-octyloxy-5-(trimethylstannyl)thiophen-2-yl)thiazolo[5,4-d]thiazole
  参考文献：
  名称：

  Thiazolothiazole Donor–Acceptor Conjugated Polymer Semiconductors for Photovoltaic Applications

  摘要：

  A series of eight new donor-acceptor conjugated copolymers based on thiazolo[5,4-d]thiazole (TT) were synthesized by Suzuki and Stile polycondensations, and their optical, electronic structure, field-effect charge transport, and photovoltaic properties were investigated. The number-average molecular weight was moderate to high (20-103 kDa) for four of the new copolymers and low (<10 kDa) for the rest. The optical band gap (1.7-2.2 eV) and the ionization potential (4.9-5.7 eV) of the copolymers could be tuned by varying the strength of the electron-donating comonomers. X-ray diffraction analysis of the neat TT polymer thin films showed that they exhibit a lamellar crystalline morphology with a (100) d-spacing of 1.449-1.881 nm. The polymers had field-effect hole mobilities of 2 X 10(-3)-3 X 10(-2) cm(2)/(V s). Although fullerene (PC71BM)-based bulk heterojunction solar cells showed that most of the new polymers had low photovoltaic power conversion efficiency (<2.4%), the standout polymer PDEHTT had a high efficiency of 5.7%. X-ray diffraction analysis and TEM imaging of PDEHTT/PC71BM blend films showed a bicontinuous nanoscale morphology with a crystalline polymer nanofiber (15-20 nm width) network.

  DOI：

  10.1021/ma500250j

文献信息

• COPOLYMER SEMICONDUCTORS COMPRISING THIAZOLOTHIAZOLE OR BENZOBISTHIAZOLE, OR BENZOBISOXAZOLE ELECTRON ACCEPTOR SUBUNITS, AND ELECTRON DONOR SUBUNITS, AND THEIR USES IN TRANSISTORS AND SOLAR CELLS
  申请人：Jenekhe Samson A.

  公开号：US20120273732A1

  公开（公告）日：2012-11-01

  The inventions disclosed, described, and/or claimed herein relate to copolymers comprising copolymers comprising electron accepting A subunits that comprise thiazolothiazole, benzobisthiazole, or benzobisoxazoles rings, and electron donating subunits that comprise certain heterocyclic groups. The copolymers are useful for manufacturing organic electronic devices, including transistors and solar cells. The invention also relates to certain synthetic precursors of the copolymers. Methods for making the copolymers and the derivative electronic devices are also described.

  本文所披露、描述和/或声明的发明涉及包含电子受体A亚单位的共聚物，该共聚物包含噻唑噻唑、苯并噻唑或苯并噁唑环的共聚物，以及包含特定杂环基团的电子给体亚单位。这些共聚物可用于制造有机电子器件，包括晶体管和太阳能电池。该发明还涉及共聚物的某些合成前体。还描述了制造共聚物和衍生电子器件的方法。
• US8871884B2
  申请人：——

  公开号：US8871884B2

  公开（公告）日：2014-10-28