1-(2-exyldecyl)-3,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-phenanthro[1,10,9,8-cdefg]carbazole | 1220707-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-(2-exyldecyl)-3,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-phenanthro[1,10,9,8-cdefg]carbazole
• 英文别名: 1-(2-hexyldecyl)-3,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-phenanthro[1,10,9,8-cdefg]carbazole；12-(2-Hexyldecyl)-9,15-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3(8),4,6,9,14,16(21),17,19-decaene；12-(2-hexyldecyl)-9,15-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3(8),4,6,9,14,16(21),17,19-decaene
• CAS: 1220707-52-7
• 化学式: C₄₈H₆₅B₂NO₄
• 分子量: 741.67
• InChiKey: RSUIEBYLOKGLGV-UHFFFAOYSA-N

物化性质

• 沸点：
  793.0±53.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.07
• 重原子数：
  55
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-exyldecyl)-3,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-phenanthro[1,10,9,8-cdefg]carbazole 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 3,10-bis(5-bromo-3-(2-ethylhexyl)thiophen-2-yl)-1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole
  参考文献：
  名称：

  菲并咔唑基无掺杂空穴传输聚合物的构象和组成调节提高钙钛矿太阳能电池的性能

  摘要：

  共轭聚合物被认为是高效稳定的钙钛矿太阳能电池 (PSC) 中无掺杂空穴传输材料 (HTM) 的有希望的候选者。迄今为止，绝大多数聚合物 HTM 具有结构复杂的苯并 [1,2-b:4,5-b'] 二噻吩 (BDT) 类似物和吸电子杂环，形成强供体 - 受体 (D-A) 结构. 在此，通过将 PC 单元插入聚合物噻吩或硒吩链中，合成了一类新的基于菲咔唑 (PC) 的聚合物 HTM（PC1、PC2 和 PC3），目的是增强相邻聚合物的 π-π 堆积。链，并通过 PC 的宽平面共轭骨架与钙钛矿表面有效相互作用。合适的能级，优异的热稳定性，通过精心调整聚合物的构象和元素组成，可以获得耐湿性和显着的光电性能。因此，含有 PC3 作为无掺杂 HTM 的 PSC 表现出 20.8% 的稳定功率转换效率 (PCE) 和显着提高的寿命，成为基于无掺杂 HTM 的最佳 PSC 类型之一。随后的实验和理论研究表明

  DOI：

  10.1021/jacs.0c08352
• 作为产物：
  描述：

  3,10-dibromo-1-(2-hexyldecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole 、 2-异丙基硼酸频那醇酯 在 正丁基锂 作用下， 以 四氢呋喃 、 light petroleum 为溶剂， 以63%的产率得到1-(2-exyldecyl)-3,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-phenanthro[1,10,9,8-cdefg]carbazole
  参考文献：
  名称：

  Tri-N-annulated Hexarylene: An Approach to Well-Defined Graphene Nanoribbons with Large Dipoles

  摘要：

  We report a highly efficient synthetic methodology toward tri-N-annulated hexarylenes from easily available N-annulated perylenes, which is favored by the oxidative ring fusion driven by DDQ/Sc(OTf)(3). To assist the characterization of the new compounds, quantum-chemical calculations of structural and spectroscopic properties have been carried out for three oligomers of N-annulated rylenes. It is shown that tri-N-annulated hexarylene dyes display remarkably large dipole moments likely associated with the formation of H aggregates, as suggested by the marked concentration dependence of the measured UV vis spectra. It is suggested that the combination of pi-pi stacking interactions and dipole dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.

  DOI：

  10.1021/ja100276x

文献信息

• Dithienopicenocarbazole-Based Acceptors for Efficient Organic Solar Cells with Optoelectronic Response Over 1000 nm and an Extremely Low Energy Loss
  作者：Zhaoyang Yao、Xunfan Liao、Ke Gao、Francis Lin、Xiaobao Xu、Xueliang Shi、Lijian Zuo、Feng Liu、Yiwang Chen、Alex K.-Y. Jen

  DOI：10.1021/jacs.7b13239

  日期：2018.2.14

  Two cheliforrn non-fullerene acceptors, DTPC-IC and DTPC-DFIC, based on a highly electron-rich core, dithienopicenocarbazole (DTPC), are synthesized, showing ultra-narrow bandgaps (as low as 1.21 eV). The two-dimensional nitrogen-containing conjugated DTPC possesses strong electron-donating Capability, which induces intense intramolecular charge transfer and intermolecular pi-pi stacking hi derived acceptors. The solar cell based on DTPC-DFIC and a spectrally complementary polymer donor, PTB7-Th, showed a high power conversion efficiency of 10.21% and an extremely low energy loss of 045 eV, which is the lowest among reported efficient OSCs.
• Tri-N-annulated Hexarylene: An Approach to Well-Defined Graphene Nanoribbons with Large Dipoles
  作者：Yan Li、Jing Gao、Simone Di Motta、Fabrizia Negri、Zhaohui Wang

  DOI：10.1021/ja100276x

  日期：2010.3.31

  We report a highly efficient synthetic methodology toward tri-N-annulated hexarylenes from easily available N-annulated perylenes, which is favored by the oxidative ring fusion driven by DDQ/Sc(OTf)(3). To assist the characterization of the new compounds, quantum-chemical calculations of structural and spectroscopic properties have been carried out for three oligomers of N-annulated rylenes. It is shown that tri-N-annulated hexarylene dyes display remarkably large dipole moments likely associated with the formation of H aggregates, as suggested by the marked concentration dependence of the measured UV vis spectra. It is suggested that the combination of pi-pi stacking interactions and dipole dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.
• Conformational and Compositional Tuning of Phenanthrocarbazole-Based Dopant-Free Hole-Transport Polymers Boosting the Performance of Perovskite Solar Cells
  作者：Zhaoyang Yao、Fuguo Zhang、Yaxiao Guo、Heng Wu、Lanlan He、Zhou Liu、Bin Cai、Yu Guo、Calvin J. Brett、Yuanyuan Li、Chinmaya Venugopal Srambickal、Xichuan Yang、Gang Chen、Jerker Widengren、Dianyi Liu、James M. Gardner、Lars Kloo、Licheng Sun

  DOI：10.1021/jacs.0c08352

  日期：2020.10.14

  phenanthrocarbazole (PC)-based polymeric HTMs (PC1, PC2, and PC3) has been synthesized by inserting a PC unit into a polymeric thiophene or selenophene chain with the aim of enhancing the π–π stacking of adjacent polymer chains and also to efficiently interact with the perovskite surface through the broad and planar conjugated backbone of the PC. Suitable energy levels, excellent thermostability, and humidity

  共轭聚合物被认为是高效稳定的钙钛矿太阳能电池 (PSC) 中无掺杂空穴传输材料 (HTM) 的有希望的候选者。迄今为止，绝大多数聚合物 HTM 具有结构复杂的苯并 [1,2-b:4,5-b'] 二噻吩 (BDT) 类似物和吸电子杂环，形成强供体 - 受体 (D-A) 结构. 在此，通过将 PC 单元插入聚合物噻吩或硒吩链中，合成了一类新的基于菲咔唑 (PC) 的聚合物 HTM（PC1、PC2 和 PC3），目的是增强相邻聚合物的 π-π 堆积。链，并通过 PC 的宽平面共轭骨架与钙钛矿表面有效相互作用。合适的能级，优异的热稳定性，通过精心调整聚合物的构象和元素组成，可以获得耐湿性和显着的光电性能。因此，含有 PC3 作为无掺杂 HTM 的 PSC 表现出 20.8% 的稳定功率转换效率 (PCE) 和显着提高的寿命，成为基于无掺杂 HTM 的最佳 PSC 类型之一。随后的实验和理论研究表明