1-(4,5-bis(chloromethyl)thiophen-2-yl)-2-ethylhexan-1-one | 1194605-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4,5-bis(chloromethyl)thiophen-2-yl)-2-ethylhexan-1-one
• 英文别名: 1-[4,5-Bis(chloromethyl)thiophen-2-yl]-2-ethylhexan-1-one
• CAS: 1194605-70-3
• 化学式: C₁₄H₂₀Cl₂OS
• 分子量: 307.284
• InChiKey: XZAQXKHKUTXQIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4,5-bis(chloromethyl)thiophen-2-yl)-2-ethylhexan-1-one 在 sodium sulfide 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 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 aluminum (III) chloride 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 1-(4,5-bis(chloromethyl)thiophen-2-yl)-2-ethylhexan-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

• Synthesis of Mono- and Bisadducts of Thieno-<i>o</i>-quinodimethane with C₆₀ for Efficient Polymer Solar Cells
  作者：Congyun Zhang、Shan Chen、Zuo Xiao、Qiqun Zuo、Liming Ding

  DOI：10.1021/ol3002392

  日期：2012.3.16

  A series of mono- and bisadducts of thieno-o-quinodimethane with C-60 (TOQC) was efficiently prepared through the Diels-Alder reaction of pristine or solubilizing side-chain-substituted 2,3-bis(chloromethyl)thiophene with C-60. The pristine TOQC bisadduct (bis-TOQC) shows much higher performance than the side-chain-substituted TOQC bisadducts in polymer solar cells, while the situation is inverse for the TOQC monoadducts. The best power conversion efficiency of 5.1% was achieved from the bis-TOQC:P3HT solar cells under simulated AM1.5G irradiation (86 mW/cm(2)).
• 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.
• CONJUGATED POLYMERS WITH CARBONYL SUBSTITUTED THIENO[3,4-B]THIOPHENE UNITS FOR POLYMER SOLAR CELL ACTIVE LAYER MATERIALS
  申请人：Hou Jianhui

  公开号：US20110017956A1

  公开（公告）日：2011-01-27

  In one embodiment of the present disclosure, a series of conjugated polymers used, among other things, as polymer solar cell or polymer photovoltaic device active layer materials, is provided. In one embodiment, the conjugated polymers have the general structure and formula shown in (I), wherein: R1 and R2 are independently selected from proton, halogens, alkyls, aryls and substituted aryls; Ar is selected from the group consisting of monocyclic, bicyclic and polycyclic arylene, or monocyclic, bicyclic and polycyclic heteroarylene. In another embodiment, the conjugated photovoltaic polymers are comprised of repeated units having the general structure of formula (II), wherein, R1, R2, R3, R4, R5, and R6 are independently selected from proton, alkyls, halogens, aryls, substituted aryls, and other kinds of substituents. Synthesis methods of several polymers of the present disclosure are provided, and absorption spectra and electrochemical cyclic voltammetry data of some polymers, and also the photovoltaic properties of the polymers in this present disclosure are also provided.
• CONJUGATED POLYMERS WITH CARBONYL-SUBSTITUTED THIENO [3,4-B] THIOPHENE UNITS FOR POLYMER SOLAR CELL ACTIVE LAYER MATERIALS
  申请人：Solarmer Energy, Inc.

  公开号：US20130123449A1

  公开（公告）日：2013-05-16

  In one embodiment of the present disclosure, a series of conjugated polymers used, among other things, as polymer solar cell or polymer photovoltaic device active layer materials, is provided. In one embodiment, the conjugated polymers have the general structure and formula shown in (I), wherein: R1 and R2 are independently selected from proton, halogens, alkyls, aryls and substituted aryls; Ar is selected from the group consisting of monocyclic, bicyclic and polycyclic arylene, or monocyclic, bicyclic and polycyclic heteroarylene. In another embodiment, the conjugated photovoltaic polymers are comprised of repeated units having the general structure of formula (II), wherein, R1, R2, R3, R4, R5, and R6 are independently selected from proton, alkyls, halogens, aryls, substituted aryls, and other kinds of substituents. Synthesis methods of several polymers of the present disclosure are provided, and absorption spectra and electrochemical cyclic voltammetry data of some polymers, and also the photovoltaic properties of the polymers in this present disclosure are also provided.
• US8372945B2
  申请人：——

  公开号：US8372945B2

  公开（公告）日：2013-02-12