2,11-bis[9,9-dioctyl-7-[5,5"""-bis(trimethylsilyl)-3',5""'-bis[5-(trimethylsilyl)-2-thienyl]-2,2':5',2":5",2'":3'",2"":5"",2""':4""',2""'-septithiophene-5'"-yl]-9H-fluoren-2-yl]hexabenzo[bc,ef,hi,kl,no,qr]coronene | 1205683-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2,11-bis[9,9-dioctyl-7-[5,5"""-bis(trimethylsilyl)-3',5""'-bis[5-(trimethylsilyl)-2-thienyl]-2,2':5',2":5",2'":3'",2"":5"",2""':4""',2""'-septithiophene-5'"-yl]-9H-fluoren-2-yl]hexabenzo[bc,ef,hi,kl,no,qr]coronene
• 英文别名: [5-[5-[5-[5-[7-[25-[7-[4,5-Bis[5-[4,5-bis(5-trimethylsilylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-9,9-dioctylfluoren-2-yl]-6-tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1(42),2(15),3,5,7,9,11,13,16(29),17,19,21,23,25,27,30,32,34,36,38,40-henicosaenyl]-9,9-dioctylfluoren-2-yl]-2-[5-[4,5-bis(5-trimethylsilylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-3-yl]thiophen-2-yl]-2-(5-trimethylsilylthiophen-2-yl)thiophen-3-yl]thiophen-2-yl]-trimethylsilane；[5-[5-[5-[5-[7-[25-[7-[4,5-bis[5-[4,5-bis(5-trimethylsilylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-9,9-dioctylfluoren-2-yl]-6-tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1(42),2(15),3,5,7,9,11,13,16(29),17,19,21,23,25,27,30,32,34,36,38,40-henicosaenyl]-9,9-dioctylfluoren-2-yl]-2-[5-[4,5-bis(5-trimethylsilylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-3-yl]thiophen-2-yl]-2-(5-trimethylsilylthiophen-2-yl)thiophen-3-yl]thiophen-2-yl]-trimethylsilane
• CAS: 1205683-90-4
• 化学式: C₁₉₆H₁₉₈S₁₈Si₈
• 分子量: 3355.6
• InChiKey: CFJVPVUFFHWWJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  66.5
• 重原子数：
  222
• 可旋转键数：
  56
• 环数：
  37.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  508
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2,11-bis[9,9-dioctyl-7-[5,5"""-bis(trimethylsilyl)-3',5""'-bis[5-(trimethylsilyl)-2-thienyl]-2,2':5',2":5",2'":3'",2"":5"",2""':4""',2""'-septithiophene-5'"-yl]-9H-fluoren-2-yl]hexabenzo[bc,ef,hi,kl,no,qr]coronene 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以96%的产率得到2,11-bis[9,9-dioctyl-7-[3',5""'-bis(2-thienyl)-2,2':5',2":5",2'":3'",2"":5"",2""':4""',2""'-septithiophene-5'"-yl]-9H-fluoren-2-yl]hexabenzo[bc,ef,hi,kl,no,qr]coronene
  参考文献：
  名称：

  芴基六亚乙基六苯并二苯并树枝状低聚噻吩杂化材料：合成，光物理性质，自缔合行为和器件性能

  摘要：

  除分子性质外，分子间作用力在定义有机电子设备的性能中起着至关重要的作用。这在块状异质结（BHJ）太阳能电池中尤为重要，在该电池中，电子供体和受体材料排列成具有理想尺寸和分布的不同晶相可以提高功率转换效率。在这项研究中，一系列芴六围通过使用会聚合成方法，获得了具有可变大小的噻吩树枝状分子（DOT）修饰的hexabenzocoronenes（FHBC）。掌握了如此多种多样的分子大小和形状后，本研究的目的是强调分子性质，本体性质和器件性能之间的关系。π–π堆积能力与树枝状聚合物生成之间的相关性是通过溶液和固态的自组织研究建立的。纳米级分子组织与源自FHBC和DOT部分的光物理特性的协同组合导致光伏性能的显着改善。

  DOI：

  10.1002/chem.201100211
• 作为产物：
  描述：

  2-[5,5''''''-bis(trimethylsilyl)-3',5'''''-bis[5-(trimethylsilyl)-2-thienyl]-2,2':5',2'':5'',2''':3''',2'''':5'''',2''''':4''''',2''''''-septithien-5'''-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 6,25-Bis(7-iodo-9,9-dioctylfluoren-2-yl)tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1(42),2(15),3,5,7,9,11,13,16(29),17,19,21,23,25,27,30,32,34,36,38,40-henicosaene 在 四(三苯基膦)钯 、 四乙基氢氧化铵 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以88%的产率得到2,11-bis[9,9-dioctyl-7-[5,5"""-bis(trimethylsilyl)-3',5""'-bis[5-(trimethylsilyl)-2-thienyl]-2,2':5',2":5",2'":3'",2"":5"",2""':4""',2""'-septithiophene-5'"-yl]-9H-fluoren-2-yl]hexabenzo[bc,ef,hi,kl,no,qr]coronene
  参考文献：
  名称：

  芴基六亚乙基六苯并二苯并树枝状低聚噻吩杂化材料：合成，光物理性质，自缔合行为和器件性能

  摘要：

  除分子性质外，分子间作用力在定义有机电子设备的性能中起着至关重要的作用。这在块状异质结（BHJ）太阳能电池中尤为重要，在该电池中，电子供体和受体材料排列成具有理想尺寸和分布的不同晶相可以提高功率转换效率。在这项研究中，一系列芴六围通过使用会聚合成方法，获得了具有可变大小的噻吩树枝状分子（DOT）修饰的hexabenzocoronenes（FHBC）。掌握了如此多种多样的分子大小和形状后，本研究的目的是强调分子性质，本体性质和器件性能之间的关系。π–π堆积能力与树枝状聚合物生成之间的相关性是通过溶液和固态的自组织研究建立的。纳米级分子组织与源自FHBC和DOT部分的光物理特性的协同组合导致光伏性能的显着改善。

  DOI：

  10.1002/chem.201100211

文献信息

• [EN] NOVEL COMPOUNDS, DERIVATIVES THEREOF AND THEIR USE IN HETEROJUNCTION DEVICES<br/>[FR] NOUVEAUX COMPOSÉS, LEURS DÉRIVÉS ET LEUR UTILISATION AU SEIN DE DISPOSITIFS À HÉTÉROJONCTION
  申请人：UNIV MELBOURNE

  公开号：WO2010060160A1

  公开（公告）日：2010-06-03

  The invention relates to novel polyaromatic and polyheteroaromatic compounds and derivatives thereof. The compounds display high solubility in organic solvents. A further aspect of the invention relates to the use of the novel compounds in the fabrication of organic film based heterojunction devices. In one form the devices display high conversion efficiencies in solar cell applications.

  该发明涉及新型多芳香和多杂芳化合物及其衍生物。这些化合物在有机溶剂中显示出很高的溶解度。该发明的另一个方面涉及将这些新型化合物用于制造基于有机薄膜的异质结器件。在某种形式中，这些器件在太阳能电池应用中显示出很高的转换效率。
• Self-Assembling Thiophene Dendrimers with a Hexa-<i>peri</i>-hexabenzocoronene Core−Synthesis, Characterization and Performance in Bulk Heterojunction Solar Cells
  作者：Wallace W. H. Wong、Chang-Qi Ma、Wojciech Pisula、Chao Yan、Xinliang Feng、David J. Jones、Klaus Müllen、René A. J. Janssen、Peter Bäuerle、Andrew B. Holmes

  DOI：10.1021/cm903272y

  日期：2010.1.26

  The solidstate organization of molecules is an important factor in determining the performance of organic electronic devices. In bulk heterojunction (BHJ) solar cells, the arrangement of electron donor and acceptor materials into distinct crystalline phases of ideal size and distribution can lead to better power conversion efficiencies. The use of fluorenyl hexa-peri-hexabenzocoronene (FHBC) 2 in this study has highlighted the importance of molecular organization to device performance. FHBC compounds 6, 8, and 10, functionalized with a series of thiophene dendrons, were synthesized using Suzuki-Miyaura coupling in high yields. In UV-vis and H-1 NMR spectroscopic studies, all FHBC derivatives showed self-association in solution. Hexagonal packing of columnar structures was observed for solid state samples of FHBC 2 and 8 in two-dimensional wide-angle X-ray scattering experiments. In thin film X-ray experiments, ordered structures were observed in blends of FHBC2 and fullerene acceptor materials indicating that there is phase separation between the donor and acceptor materials and that the self-organization of the FHBC material is unaffected. While the large thiophene dendritic substituent attached to compound 10 broadened its UV-vis absorption profile, the solid state morphology is altered by the bulky thiophene dendrons. These molecular structure variations arc reflected in the performance characteristics of BHJ solar cell devices fabricated using these FHBC compounds as electron donor materials. Power conversion deficiency of 2.5% was achieved for a device containing cornpound 10 with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as the acceptor material. This compares favorably with devices fabricated with pure dendritic thiophene materials and illustrates the positive effect of molecular self-organization on device performance.
• Fluorenyl Hexa-peri-hexabenzocoronene-Dendritic Oligothiophene Hybrid Materials: Synthesis, Photophysical Properties, Self-Association Behaviour and Device Performance
  作者：Wallace W. H. Wong、Chang-Qi Ma、Wojciech Pisula、Alexey Mavrinskiy、Xinliang Feng、Helga Seyler、David J. Jones、Klaus Müllen、Peter Bäuerle、Andrew B. Holmes

  DOI：10.1002/chem.201100211

  日期：2011.5.9

  a series of fluorenyl hexa‐peri‐hexabenzocoronenes (FHBC) decorated with thiophene dendrons (DOT) of variable size was obtained by using a convergent synthetic approach. With such variety of molecular sizes and shapes in hand, the objective of this study is to highlight the relationships between molecular properties, bulk properties and device performance. Correlations between π–π stacking ability and

  除分子性质外，分子间作用力在定义有机电子设备的性能中起着至关重要的作用。这在块状异质结（BHJ）太阳能电池中尤为重要，在该电池中，电子供体和受体材料排列成具有理想尺寸和分布的不同晶相可以提高功率转换效率。在这项研究中，一系列芴六围通过使用会聚合成方法，获得了具有可变大小的噻吩树枝状分子（DOT）修饰的hexabenzocoronenes（FHBC）。掌握了如此多种多样的分子大小和形状后，本研究的目的是强调分子性质，本体性质和器件性能之间的关系。π–π堆积能力与树枝状聚合物生成之间的相关性是通过溶液和固态的自组织研究建立的。纳米级分子组织与源自FHBC和DOT部分的光物理特性的协同组合导致光伏性能的显着改善。