2,2'-(2,5-dibromobenzene-1,4-diyl)bis(3-bromo-5-trimethylsilylthiophene) | 1217503-07-5

• 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: 2,2'-(2,5-dibromobenzene-1,4-diyl)bis(3-bromo-5-trimethylsilylthiophene)
• 英文别名: (5,5'-(2,5-dibromo-1,4-phenylene)bis(4-bromothiophene-5,2-diyl))bis(trimethylsilane)；2,2'-(2,5-Dibromobenzene-1,4-diyl)bis(3-bromo-5-trimethylsilyl-thiophene)；[4-bromo-5-[2,5-dibromo-4-(3-bromo-5-trimethylsilylthiophen-2-yl)phenyl]thiophen-2-yl]-trimethylsilane
• CAS: 1217503-07-5
• 化学式: C₂₀H₂₂Br₄S₂Si₂
• 分子量: 702.314
• InChiKey: TWNYLHZQVZKVGY-UHFFFAOYSA-N

物化性质

• 沸点：
  537.4±50.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.28
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2'-(2,5-dibromobenzene-1,4-diyl)bis(3-bromo-5-trimethylsilylthiophene) 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 16.5h， 生成 2,7-双三甲基锡-苯并[1,2-B:4,5-B]双(4,4'-二辛基-4H-二噻吩并噻咯)-双三甲基锡
  参考文献：
  名称：

  Silaindacenodithiophene-Based Molecular Donor: Morphological Features and Use in the Fabrication of Compositionally Tolerant, High-Efficiency Bulk Heterojunction Solar Cells

  摘要：

  A novel solution-processable small molecule, namely, benzo[1,2-b:4,5-b]bis(4,4'-dihexyl-4H-silolo[3,2-b]-thiophene-2,2'-diyl)bis(6-fluoro-4-(5'-hexyl-[2,2'-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole (p-SIDT(FBTTh2)(2)), was designed and synthesized by utilizing the silaindacenodithiophene (SIDT) framework as the central D-2 donor unit within the D(1)AD(2)AD(1) chromophore configuration. Relative to the widely studied 7,7'-[4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b']dithiophene-2,6-diyl]bis [6-fluoro-4-(5'-hexyl-[2,2 '-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole] (p-DTS(FBTTh2)(2)), which contains the stronger donor fragment clithienosilole (DTS) as D-2, one finds that p-SIDT(FBTTh2)(2) exhibits a wider band gap and can be used to fabricate bulk heterojunction solar cells with higher open circuit voltage (0.91 V). Most remarkably, thin films comprising p-SIDT(FBTTh2)(2) can achieve exceptional levels of self-organization directly via solution deposition. For example, high-resolution transmission electron microscopy analysis shows that p-SIDT(FBTTh2)(2) spin-cast from chlorobenzene organizes into crystalline domains with lattice planes that extend over length scales on the order of hundreds of nanometers. Such features suggest liquid crystalline properties during the evolution of the film. Moreover, grazing incidence wide-angle X-ray scattering analysis shows a strong tendency for the molecules to exist with a strong "face-on" orientation relative to the substrate plane. Similar structural features, albeit of more restricted dimensions, can be observed within p-SIDT(FBTTh2)(2):PC7IBM bulk heterojunction thin films when the films are processed with 0.4% diiodooctane (DIO) solvent additive. DIO use also increases the solar cell power conversion efficiencies (PCEs) from 1.7% to 6.4%. Of significance from a practical device fabrication perspective is that, for p-SIDT(FBTTh2)(2):PC71BM blends, there is a wide range of compositions (from 20:80 to 70:30 p-SIDT(FBTTh2)(2):PC71BM) that provide good photovoltaic response, i.e., PCE = 4-6%, indicating a robust tendency to form the necessary continuous phases for charge carrier collection. Light intensity photocurrent measurements, charge selective diode fabrication, and internal quantum efficiency determinations were carried out to obtain insight into the mechanism of device operation. Inclusion of DIO in the casting solution results in films that exhibit much lower photocurrent dependence on voltage and a concomitant increase in fill factor. At the optimum blend ratio, devices show high charge carrier mobilities, while mismatched hole and electron mobilities in blends with high or low donor content result in reduced fill factors and device performance.

  DOI：

  10.1021/ja412473p
• 作为产物：
  描述：

  1,4-二溴-2,5-二碘苯 在 四(三苯基膦)钯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 0.5h， 生成 2,2'-(2,5-dibromobenzene-1,4-diyl)bis(3-bromo-5-trimethylsilylthiophene)
  参考文献：
  名称：

  [EN] NON-FULLERENE ELECTRON ACCEPTORS
  [FR] ACCEPTEURS D'ÉLECTRONS SANS FULLERÈNE

  摘要：

  该发明提供了式（I）的电子受体化合物，可用于光学或电子器件的有机组合物中。

  公开号：

  WO2017191468A1

文献信息

• Germaindacenodithiophene based low band gap polymers for organic solar cells
  作者：Zhuping Fei、Raja Shahid Ashraf、Zhenggang Huang、Jeremy Smith、R. Joseph Kline、Pasquale D'Angelo、Thomas D. Anthopoulos、James R. Durrant、Iain McCulloch、Martin Heeney

  DOI：10.1039/c2cc17996b

  日期：——

  a fused germaindacenodithiophene monomer and its polymerisation with 2,1,3-benzothiadiazole by Suzuki polycondensation. The resulting polymer, PGeTPTBT, is semicrystalline, despite the presence of four bulky 2-ethylhexyl groups. Blends with P(70)CBM afford solar cells with efficiencies of 5.02%.

  我们报告了首个熔融的germaindacenodithiothioe单体的合成及其通过Suzuki缩聚反应与2,1,3-苯并噻二唑的聚合反应。尽管存在四个庞大的2-乙基己基，但所得聚合物PGeTPTBT仍是半结晶的。与P（70）CBM混合可提供效率为5.02％的太阳能电池。
• 헤테로환 화합물 및 이를 포함하는 유기 태양 전지
  申请人：LG CHEM, LTD. 주식회사 엘지화학(120010134563) Corp. No ▼ 110111-2207995BRN ▼107-81-98139

  公开号：KR20150121661A

  公开（公告）日：2015-10-29

  본 명세서는 헤테로환 화합물 및 이를 포함하는 유기 태양 전지에 관한 것이다.

  本规范书涉及异芳烃化合物及其在有机太阳能电池中的应用。
• Polymers Derived from Benzobis(silolothiophene) and their Use as Organic Semiconductors
  申请人：Tierney Steven

  公开号：US20110168953A1

  公开（公告）日：2011-07-14

  The invention relates to conjugated polymers comprising benzo-bis(silolothiophene) units or derivatives thereof, to methods of their preparation, to novel monomer units used therein, to the use of the polymers in organic electronic (OE) devices, and to OE devices comprising the polymers.

  本发明涉及包含苯基噻吩硅杂环并联聚物或其衍生物，其制备方法，用于其中的新型单体单位，聚合物在有机电子（OE）器件中的应用，以及包含聚合物的OE器件。
• Polymers derived from benzobis(silolothiophene) and their use as organic semiconductors
  申请人：Tierney Steven

  公开号：US08709290B2

  公开（公告）日：2014-04-29

  The invention relates to conjugated polymers comprising benzo-bis(silolothiophene) units or derivatives thereof, to methods of their preparation, to novel monomer units used therein, to the use of the polymers in organic electronic (OE) devices, and to OE devices comprising the polymers.

  该发明涉及包含苯并[硅苯并噻吩]单元或其衍生物的共轭聚合物，以及其制备方法、在其中使用的新型单体单元、在有机电子（OE）器件中使用该聚合物以及包含该聚合物的OE器件。
• Benzobis(silolothiophene)-Based Low Bandgap Polymers for Efficient Polymer Solar Cells
  作者：Jie-Yu Wang、Steven K. Hau、Hin-Lap Yip、Joshua A. Davies、Kung-Shih Chen、Yong Zhang、Ying Sun、Alex K.-Y. Jen

  DOI：10.1021/cm1020228

  日期：2011.2.8