8,17-dibromo-7,9,16,18-tetraazabenzodifluoranthene-3,4,12,13-tetracarboxylic acid diimide | 1443122-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8,17-dibromo-7,9,16,18-tetraazabenzodifluoranthene-3,4,12,13-tetracarboxylic acid diimide
• 英文别名: 5,23-Dibromo-14,32-bis(2-decyltetradecyl)-3,7,14,21,25,32-hexazaundecacyclo[28.6.2.29,12.02,26.04,24.06,22.08,20.010,19.011,16.027,37.034,38]tetraconta-1(37),2(26),3,5,7,9,11,16,18,20,22,24,27,29,34(38),35,39-heptadecaene-13,15,31,33-tetrone
• CAS: 1443122-19-7
• 化学式: C₈₂H₁₀₆Br₂N₆O₄
• 分子量: 1399.59
• InChiKey: SPXITWJKKQWBOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28.7
• 重原子数：
  94
• 可旋转键数：
  44
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8,17-dibromo-7,9,16,18-tetraazabenzodifluoranthene-3,4,12,13-tetracarboxylic acid diimide 、 2-三丁基甲锡烷基噻吩 在 三(邻甲基苯基)磷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以67%的产率得到14,32-Bis(2-decyltetradecyl)-23-thiophen-2-yl-5-thiophen-2-yl-3,7,14,21,25,32-hexazaundecacyclo[28.6.2.29,12.02,26.04,24.06,22.08,20.010,19.011,16.027,37.034,38]tetraconta-1(37),2(26),3,5,7,9,11,16,18,20,22,24,27,29,34(38),35,39-heptadecaene-13,15,31,33-tetrone
  参考文献：
  名称：

  四氮杂苯并二氟蒽二酰亚胺：可溶液处理的n型有机半导体的构建基块

  摘要：

  合成了11环杂环二酰亚胺，发现它们是平面的，并表现出滑动的面对面π堆叠。取代基的变化调节了电子结构和性能。在n沟道有机场效应晶体管中，新的有机半导体具有很高的电子迁移率。当将它们用作聚合物太阳能电池中的受体材料时，获得了1.8％的功率转换效率。

  DOI：

  10.1002/anie.201210085
• 作为产物：
  描述：

  3,6-dibromo-1,2,4,5-benzenetetramine 、 2-(2-decyltetradecyl)-1H-indeno[6,7,1-def]isoquinoline-1,3,6,7(2H)-tetraone 在 溶剂黄146 作用下， 以54.6%的产率得到8,17-dibromo-7,9,16,18-tetraazabenzodifluoranthene-3,4,12,13-tetracarboxylic acid diimide
  参考文献：
  名称：

  四氮杂苯并二氟蒽二酰亚胺：可溶液处理的n型有机半导体的构建基块

  摘要：

  合成了11环杂环二酰亚胺，发现它们是平面的，并表现出滑动的面对面π堆叠。取代基的变化调节了电子结构和性能。在n沟道有机场效应晶体管中，新的有机半导体具有很高的电子迁移率。当将它们用作聚合物太阳能电池中的受体材料时，获得了1.8％的功率转换效率。

  DOI：

  10.1002/anie.201210085

文献信息

• NON-FULLERENE ELECTRON ACCEPTORS FOR ORGANIC PHOTOVOLTAIC DEVICES
  申请人：UNIVERSITY OF WASINGTON

  公开号：US20170057962A1

  公开（公告）日：2017-03-02

  Non-fullerene electron acceptors for highly efficient organic photovoltaic devices are described. The non-fullerene electron acceptors have an extended, rigid, π-conjugated electron-deficient framework that can facilitate exciton and charge derealization. The non-fullerene electron acceptors can physically mix with a donor polymer and facilitate improved electron transport. The non-fullerene electron acceptors can be incorporated into organic electronic devices, such as photovoltaic cells.

  描述了用于高效有机光伏器件的非富勒烯电子受体。这些非富勒烯电子受体具有扩展的、刚性的、π共轭的电子亏损框架，可以促进激子和电荷的去局化。非富勒烯电子受体可以与给体聚合物物理混合，并促进改善的电子输运。非富勒烯电子受体可以被纳入有机电子器件，如光伏电池中。
• [EN] ACENAPHTHYLENE IMIDE-DERIVED SEMICONDUCTORS<br/>[FR] SEMI-CONDUCTEURS DÉRIVÉS D'ACÉNAPHTHYLÈNE IMIDE
  申请人：UNIV WASHINGTON CT COMMERCIALI

  公开号：WO2014031750A1

  公开（公告）日：2014-02-27

  Novel acenaphthylene imide-derived semiconductor materials, including small molecule compounds, polymers and oligomers. Also provided are methods for making the novel semiconductor materials and the use of the novel semiconducting materials in electronic or optoelectronic device. In some embodiments, the novel semiconducting materials are used as n-channel component in organic field-effect transistors as well as complementary electronic circuits including inverters. High mobility can be achieved.

  新型蒽醌衍生半导体材料，包括小分子化合物、聚合物和寡聚物。还提供了制备新型半导体材料的方法以及在电子或光电子器件中使用新型半导体材料的方法。在一些实施例中，新型半导体材料被用作有机场效应晶体管中的n型通道组件，以及包括反相器在内的互补电子电路。可以实现高迁移率。
• ACENAPHTHYLENE IMIDE-DERIVED SEMICONDUCTORS
  申请人：University of Washington Through its Center for Commercialization

  公开号：US20150243906A1

  公开（公告）日：2015-08-27

  Novel acenaphthylene imide-derived semiconductor materials, including small molecule compounds, polymers and oligomers. Also provided are methods for making the novel semiconductor materials and the use of the novel semiconducting materials in electronic or optoelectronic device. In some embodiments, the novel semiconducting materials are used as n-channel component in organic field-effect transistors as well as complementary electronic circuits including inverters. High mobility can be achieved.

  提供了一种新的基于乙酰萘亚胺的半导体材料，包括小分子化合物、聚合物和寡聚物。还提供了制备新型半导体材料的方法以及在电子或光电器件中使用新型半导体材料的用途。在某些实施例中，新型半导体材料被用作有机场效应晶体管中的n型组件，以及包括反相器在内的互补电子电路。可以实现高迁移率。
• Beyond Fullerenes: Design of Nonfullerene Acceptors for Efficient Organic Photovoltaics
  作者：Haiyan Li、Taeshik Earmme、Guoqiang Ren、Akinori Saeki、Saya Yoshikawa、Nishit M. Murari、Selvam Subramaniyan、Matthew J. Crane、Shu Seki、Samson A. Jenekhe

  DOI：10.1021/ja508472j

  日期：2014.10.15

  New electron-acceptor materials are long sought to overcome the small photovoltage, high-cost, poor photochemical stability, and other limitations of fullerene-based organic photovoltaics. However, all known nonfullerene acceptors have so far shown inferior photovoltaic properties compared to fullerene benchmark [6,6]-phenyl-C-60-butyric acid methyl ester (PC60BM), and there are as yet no established design principles for realizing improved materials. Herein we report a design strategy that has produced a novel multichromophoric, large size, nonplanar three-dimensional (3D) organic molecule, DBFI-T, whose pi-conjugated framework occupies space comparable to an aggregate of 9 [C-60]-fullerene molecules. Comparative studies of DBFI-T with its planar monomeric analogue (BFI-P2) and PC60BM in bulk heterojunction (BHJ) solar cells, by using a common thiazolothiazole-dithienosilole copolymer donor (PSEHTT), showed that DBFI-T has superior charge photogeneration and photovoltaic properties; PSEHTT:DBFI-T solar cells combined a high short-circuit current (10.14 mA/cm(2)) with a high open-circuit voltage (0.86 V) to give a power conversion efficiency of 5.0%. The external quantum efficiency spectrum of PSEHTT:DBFI-T devices had peaks of 60-65% in the 380-620 nm range, demonstrating that both hole transfer from photoexcited DBFI-T to PSEHTT and electron transfer from photoexcited PSEHTT to DBFI-T contribute substantially to charge photogeneration. The superior charge photogeneration and electron-accepting properties of DBFI-T were further confirmed by independent Xenon-flash time-resolved microwave conductivity measurements, which correctly predict the relative magnitudes of the conversion efficiencies of the BHJ solar cells: PSEHTT:DBFI-T > PSEHTT:PC60BM > PSEHTT:BFI-P2. The results demonstrate that the large size, multichromophoric, nonplanar 3D molecular design is a promising approach to more efficient organic photovoltaic materials.
• US9508937B2
  申请人：——

  公开号：US9508937B2

  公开（公告）日：2016-11-29