2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one | 1194605-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one
• 英文别名: 2-ethyl-1-thieno[3,4-b]thiophene-2yl-hexan-1-one；2-Ethyl-1-thieno[2,3-c]thiophen-2-ylhexan-1-one
• CAS: 1194605-74-7
• 化学式: C₁₄H₁₈OS₂
• 分子量: 266.428
• InChiKey: QUDFKKSCXOANSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 60.0h， 生成
  参考文献：
  名称：

  Design, synthesis and photophysical properties of A-D-A-D-A small molecules for photovoltaic application

  摘要：

  A series of linear-conjugated small molecule compounds featured with the acceptor-donor-acceptor-donor-acceptor (A-D-A-D-A) structure were designed, synthesized and characterized. The films of the compounds showed a broad UV-Vis absorption range of 300-800 nm with high molar absorption coefficient of more than 1.0 x 10(4) cm(-1). Their hole-mobility can be as high as 1.0 x 10(-3) cm(2) V-1 s(-1). The compounds have a compatible HOMO energy level of -5.0 eV to PC71BM and a high solubility up to 20 mg mL(-1) in chloroform. Therefore, compounds can blend with PC71BM in the chloroform and form an active layer for a photovoltaic cell device by spin-coating of the blend solution. A maximum power conversion efficiency of 3.2% was achieved with the DERH3TT solar cell device. These results indicate that the A-D-A-D-A small molecules with electron-withdrawing dyes as terminals are promising candidates for the high efficiency solution processed organic photovoltaic cells. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.05.009
• 作为产物：
  描述：

  2-乙基己酰氯 在 sodium sulfide 、 aluminum (III) chloride 、 四氯化钛 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-ethyl-1-(thieno[3,4-b]thiophen-2-yl)hexan-1-one
  参考文献：
  名称：

  Design, synthesis and photophysical properties of A-D-A-D-A small molecules for photovoltaic application

  摘要：

  A series of linear-conjugated small molecule compounds featured with the acceptor-donor-acceptor-donor-acceptor (A-D-A-D-A) structure were designed, synthesized and characterized. The films of the compounds showed a broad UV-Vis absorption range of 300-800 nm with high molar absorption coefficient of more than 1.0 x 10(4) cm(-1). Their hole-mobility can be as high as 1.0 x 10(-3) cm(2) V-1 s(-1). The compounds have a compatible HOMO energy level of -5.0 eV to PC71BM and a high solubility up to 20 mg mL(-1) in chloroform. Therefore, compounds can blend with PC71BM in the chloroform and form an active layer for a photovoltaic cell device by spin-coating of the blend solution. A maximum power conversion efficiency of 3.2% was achieved with the DERH3TT solar cell device. These results indicate that the A-D-A-D-A small molecules with electron-withdrawing dyes as terminals are promising candidates for the high efficiency solution processed organic photovoltaic cells. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.05.009

文献信息

• Regioregular Low Bandgap Polymer with Controlled Thieno[3,4-<i>b</i>]thiophene Orientation for High-Efficiency Polymer Solar Cells
  作者：Honggi Kim、Hyungjin Lee、Donghyun Seo、Youngjun Jeong、Keun Cho、Jaechol Lee、Youngu Lee

  DOI：10.1021/acs.chemmater.5b00632

  日期：2015.4.28

  The regioregular p-type copolymer PBDTTT-C-T composed of TT-BDT-TT-BDT repeating units (TT = thieno[3,4-b]thiophene, BDT = benzo[1,2-b:4,5-b′]dithoiphene) and perfectly controlled TT orientation was synthesized. The optical, thermal, and electrochemical properties of the regioregular PBDTTT-C-T were characterized and compared with the random PBDTTT-C-T without structural regioregularity. The regioregular PBDTTT-C-T showed lower optical bandgap (1.55 eV) and higher degree of crystallinity compared to the random PBDTTT-C-T. The inverted bulk heterojunction PSCs based on the regioregular PBDTTT-C-T exhibited a power conversion efficiency as high as 7.79%, which is 19% higher than the random PBDTTT-C-T-based PSCs. It was found that the improved photoabsorption and increase in charge carrier mobility due to high regioregularity of conjugated polymer backbones and effective ordering between polymer chains are the most likely reasons for enhancement of power conversion efficiency in PSCs.

  由TT-BDT-TT-BDT重复单元（TT = 噻吩并[3,4-b]噻吩，BDT = 苯并[1,2-b:4,5-b′]二噻吩）组成的p型共聚物PBDTTT-C-T和完全受控的TT取向被合成。对具有结构规整性的PBDTTT-C-T的光学、热学和电化学性质进行了表征，并与无结构规整性的无规PBDTTT-C-T进行了比较。与无规PBDTTT-C-T相比，具有结构规整性的PBDTTT-C-T具有更低的带隙（1.55 eV）和更高的结晶度。基于具有结构规整性的PBDTTT-C-T的反型体异质结光伏电池的功率转换效率高达7.79%，比基于无规PBDTTT-C-T的光伏电池高19%。研究发现，共轭聚合物主链的高结构规整性和聚合物链之间的有效有序化提高了光吸收和载流子迁移率，这很可能是提高光伏电池功率转换效率的最主要原因。
• BLOCK COPOLYMER AND PHOTOELECTRIC CONVERSION ELEMENT
  申请人：Kuraray Co., Ltd.

  公开号：EP2692760A1

  公开（公告）日：2014-02-05

  Provide are: a conjugated block copolymer capable of increasing the amount of optical absorption by a photoelectric conversion active layer and controlling the morphology thereof and capable of achieving excellent photoelectric conversion efficiency; and a photoelectric conversion element comprising a composition including an electron accepting material and this kind of conjugated block polymer. A π-electron conjugated block copolymer comprising: a polymer block (A) which involving a monomer unit having at least one heteroaryl skeleton selected from the group consisting of a fused π-conjugated skeleton, a fluorene, a carbazole, a dibenzosilole and a dibenzogermole containing at least one thiophene ring in a part of a chemical structure thereof; and a polymer block (B) involving a monomer unit of a thiophene-2,5-diyl group having a substituent at least at a 3-position thereof.

  提供：一种共轭嵌段聚合物，能够增加光电转换活性层的光吸收量并控制其形态，从而实现优异的光电转换效率；以及一种光电转换元件，其组成包括电子接受材料和这种共轭嵌段聚合物。一种π电子共轭嵌段聚合物，包括聚合物嵌段(A)，其单体单元至少具有一个杂芳基骨架，该杂芳骨架选自熔融π-共轭骨架、芴、咔唑、二苯并硅唑和二苯并锗醚组成的组；以及聚合物嵌段(B)，其单体单元为噻吩-2,5-二基，至少在其 3 位具有取代基。
• Copolymer and organic solar cell comprising same
  申请人：LG CHEM, LTD.

  公开号：US10355214B2

  公开（公告）日：2019-07-16

  The present specification relates to a copolymer and an organic solar cell comprising the same.

  本说明书涉及一种共聚物和由其组成的有机太阳能电池。
• Synthesis of a Low Band Gap Polymer and Its Application in Highly Efficient Polymer Solar Cells
  作者：Jianhui Hou、Hsiang-Yu Chen、Shaoqing Zhang、Ruby I. Chen、Yang Yang、Yue Wu、Gang Li

  DOI：10.1021/ja9064975

  日期：2009.11.4

  HOMO level of the PBDTTT-based polymer was successfully reduced by introducing an keton group in place of the ester group. The average PCE of the PBDTTT-based devices reached 6.3% with a champion PCE result of 6.58%. Due to its highly efficient photovoltaic performance and more feasible synthesis approach, PBDTTT-C has the potential to be successfully applied in the large-scale manufacturing of polymer solar cells.
• Highly Stable Polymer Solar Cells Based on Poly(dithienobenzodithiophene-<i>co</i>-thienothiophene)
  作者：Nara Shin、Hui-Jun Yun、Youngwoon Yoon、Hae Jung Son、Sang-Yong Ju、Soon-Ki Kwon、BongSoo Kim、Yun-Hi Kim

  DOI：10.1021/acs.macromol.5b00514

  日期：2015.6.23

  It is important to develop new denor (D)acceptor (A) type low band gap polymers for highly stable polymer solar cells (PSCs). Here, we describe the synthesis and photovoltaic properties of two D-A type low band gap polymers. The polymers consist of dithienobentodfthiophene (DTBDT) moieties with expanded conjugation side: groups as donors and 2-ethyl-1-(thieno[3,4-b]thiophen-2yl)hwtan-1-one (TTEH) or 6-octyl-5H-thieno[3',4':4,5]thieno[2,3-c]pyrrole-5,7(6H)-dione (DTPD) as acceptors to give pDTBDT-TTEH and pDTBDT-DTPD polymers, respectively. The pDTBDT-TTEH is quite flat, resulting in a highly crystalline film. In contrast, the pDTBDT-DTPD is highly twisted to yield an amorphous film. Photovoltaic devices based on pDTBDT-TTEH and pDTBDT-DTPD exhibited power conversion efficiencies (PCEs) of 6.74% and 4.44%, respectively. The PCE difference results mainly from morphological differences between the two polymer:PC71BM blend films; the pDTBDT-TTEH polymer formed a nanoscopically networked domains in the blend state, while the pDTBDT-DTPD polymer film contained aggregated domains with large phase separation between the poly-mer and PC71BM molecules. Importantly, we observed that pDTBDT-TTEH-based devices showed excellent stability-in air, retaining 95% of the initial PCE after storage for over 1000 h without encapsulation. The high stability of the pDTBDT-TTEH-based device was originated mainly by the crystalline nature of the pDTBDT-TTEH:PC71BM film. This work suggests that designing highly conjugated planar backboned polymers is crucial to improve not only the photovoltaic performance but also the stability of PSCs.