4,6-dibromothieno[3,4-b]thiophene-2-carboxyaldehyde | 1268347-36-9

• 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: 4,6-dibromothieno[3,4-b]thiophene-2-carboxyaldehyde
• 英文别名: 6-dibromothieno[3,4-b]thiophene-2-carboxyaldehyde；4,6-dibromothieno[3,4-b]thiophene-2-carbaldehyde；4,6-Dibromothieno[3,4-b]thiophene-2-carbaldehyde；4,6-dibromothieno[2,3-c]thiophene-2-carbaldehyde
• CAS: 1268347-36-9
• 化学式: C₇H₂Br₂OS₂
• 分子量: 326.032
• InChiKey: BQTMFIQLKKSHCW-UHFFFAOYSA-N

物化性质

• 沸点：
  406.5±40.0 °C(Predicted)
• 密度：
  2.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-dibromothieno[3,4-b]thiophene-2-carboxyaldehyde 、 氰基乙酸辛酯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以72.8%的产率得到2-cyano-3-(4,6-dibromothieno[3,4-b]thiophen-2-yl) acrylic octyl ester
  参考文献：
  名称：

  Low band gap benzothiophene–thienothiophene copolymers with conjugated alkylthiothieyl and alkoxycarbonyl cyanovinyl side chains for photovoltaic applications

  摘要：

  烷基硫代苯并噻吩（BDT）和烷氧羰基氰乙烯基修饰的噻吩噻吩（TT）被共聚合，以获得一种新的低带隙共聚物PBDTTT-S-CN，其效率为7.00%。

  DOI：

  10.1039/c4cc10062j
• 作为产物：
  描述：

  thieno[3,4-b]thiophen-2-ylmethanol 在 N-溴代丁二酰亚胺(NBS) 、 重铬酸吡啶 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 9.0h， 生成 4,6-dibromothieno[3,4-b]thiophene-2-carboxyaldehyde
  参考文献：
  名称：

  由基于二烷氧基苯并二噻吩和噻吩的稠合芳环组成的窄带隙π共轭聚合物的合成和光伏行为

  摘要：

  π共轭聚合物PBDT-CNETT和PBDT-CNECPDT是通过Stille交叉偶联聚合制备的。通过紫外可见光谱和热重分析研究了所得聚合物的光学和热性能。PBDT-CNETT和PBDT-CNECPDT分别显示出1.39 eV和1.13 eV的非常窄的带隙。表面分析仪估计的PBDT-CNETT和PBDT-CNECPDT的最高占据分子轨道能级分别为-5.17和-5.11 eV 。使用ITO / PEDOT-PSS / polymer：PC 61的电池配置对基于这些聚合物的太阳能电池进行了评估BH / LiF / Al。对于PBDT-CNETT和PBDT-CNECPDT，太阳能电池的功率转换效率估计分别为1.57和0.16％。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年

  DOI：

  10.1002/pola.24564

文献信息

• 신규한 유기 반도체 화합물, 이의 제조방법 및 이를 포함하는 유기 전자 소자
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR20150069119A

  公开（公告）日：2015-06-23

  본 발명은 신규한 유기 반도체 화합물, 이의 제조방법 및 이를 함유한 유기 전자 소자를 제공하며, 상기 유기 반도체 화합물은 전정색 영역의 흡수 스펙트럼을 가짐으로써 광자를 폭넓게 흡수할 수 있는 장점을 가져 이를 포함하는 유기 전자 소자의 광전변환재료로 유용하게 사용할 수 있다.

  本发明提供了一种新型有机半导体化合物、其制备方法以及包含其的有机电子器件。所述有机半导体化合物具有吸收光谱在全色谱范围内的优点，可以广泛吸收光子，因此可以作为包含其的有机电子器件的光电转换材料而被有用地使用。
• Novel fulleropyrrolidines bearing π-conjugated thiophene derivatives as compatibilizing group for developing highly stable polymer solar cells
  作者：Rathinam Raja、Wei-Shin Liu、Chuen-Yo Hsiow、Yen-Ju Hsieh、Syang-Peng Rwei、Wen-Yen Chiu、Leeyih Wang

  DOI：10.1016/j.orgel.2014.06.013

  日期：2014.10

  A series of new fulleropyrrolidines, which comprise one terthiophene (3T) or dithienyl thienothiophene (2TTT) conjugated segment along with two hexyl (H) or ethylhexyl (EH) chains, abbreviated as 3T-H-C-60, 3T-EH-C-60, 2TTT-H-C-60 and 2TTT-EH-C-60, were designed and synthesized to improve their structural compatibility with poly(3-hexylthiophene) (P3HT). These [60]fullerene monoadducts exhibit a characteristic UV-Vis absorption band, associated with the conjugated substituent, and similar optical bandgaps and lowest unoccupied molecular orbital (LUMO) levels of approximately 1.71 eV and -3.72 eV, respectively. The influence of the structure of the substituent in the fulleropyrrolidine on its intermolecular packing within a polymer matrix was investigated. Photoluminescence measurements of the blended films of such C-60 derivatives with P3HT reveal that the interfacial area between the two materials is larger in the 3T-based system than in the 2TTT-based system; moreover, the branched ethylhexyl chain is more effective than the linear hexyl group in reducing the size of the phase domains. Transmission electron microscopic images further confirm that relatively serious phase segregation occurs in the 2TTT-C-60/P3HT films. Accordingly, solar cells with 3T-C-60/P3HT as the active layer have an increased short-circuit current density owing to improved exciton dissociation efficiency, but 2TTT-C-60/P3HT devices have a boosted fill factor, owing to the formation of less obstructed pathways for the transport of charge carriers. More interestingly, both 3T-EH-C-60/P3HT and 2TTT-EH-C-60/P3HT exhibit highly stable blend morphology and the solar cells that are derived from them have extremely steady power conversion efficiency against long-term aging at high temperature. (C) 2014 Elsevier B.V. All rights reserved.
• Low band gap benzothiophene–thienothiophene copolymers with conjugated alkylthiothieyl and alkoxycarbonyl cyanovinyl side chains for photovoltaic applications
  作者：Kui Feng、Xiaopeng Xu、Zuojia Li、Ying Li、Kai Li、Ting Yu、Qiang Peng

  DOI：10.1039/c4cc10062j

  日期：——

  Alkylthiothieyl substituted benzothiophene (BDT) and alkoxycarbonyl cyanovinyl modified thienothiophene (TT) were copolymerized to obtain a new low band gap copolymer PBDTTT-S-CN with a efficiency of 7.00%.

  烷基硫代苯并噻吩（BDT）和烷氧羰基氰乙烯基修饰的噻吩噻吩（TT）被共聚合，以获得一种新的低带隙共聚物PBDTTT-S-CN，其效率为7.00%。
• Synthesis and photovoltaic behaviors of narrow-band-gap π-conjugated polymers composed of dialkoxybenzodithiophene- and thiophene-based fused aromatic rings
  作者：Kwang-hoi Lee、Ho-Jin Lee、Kazuhide Morino、Atsushi Sudo、Takeshi Endo

  DOI：10.1002/pola.24564

  日期：2011.3.15

  π‐Conjugated polymers, PBDT‐CNETT and PBDT‐CNECPDT, were prepared by the Stille cross‐coupling polymerization. Optical and thermal properties of the obtained polymers were investigated by UV–vis spectroscopy and thermogravimetric analysis. PBDT‐CNETT and PBDT‐CNECPDT exhibited very narrow band gaps of 1.39 and 1.13 eV, respectively. Highest occupied molecular orbital energy levels estimated by surface

  π共轭聚合物PBDT-CNETT和PBDT-CNECPDT是通过Stille交叉偶联聚合制备的。通过紫外可见光谱和热重分析研究了所得聚合物的光学和热性能。PBDT-CNETT和PBDT-CNECPDT分别显示出1.39 eV和1.13 eV的非常窄的带隙。表面分析仪估计的PBDT-CNETT和PBDT-CNECPDT的最高占据分子轨道能级分别为-5.17和-5.11 eV 。使用ITO / PEDOT-PSS / polymer：PC 61的电池配置对基于这些聚合物的太阳能电池进行了评估BH / LiF / Al。对于PBDT-CNETT和PBDT-CNECPDT，太阳能电池的功率转换效率估计分别为1.57和0.16％。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年