N,N'-二(2-乙基己基)-1,7-二(噻吩-2-基)-3,4,9,10-苝四羧酸二酰亚胺 | 851786-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: N,N'-二(2-乙基己基)-1,7-二(噻吩-2-基)-3,4,9,10-苝四羧酸二酰亚胺
• 英文名称: N,N'-di(2-ethylhexyl)-1,7-dithien-2-yl-3,4,9,10-perylenediimide
• 英文别名: N,N'-di(2-ethylhexyl)-1,7-di(thiophen-2-yl)perylene-3,4,9,10-tetracarboxylic acid diimide；N,N'-di(2-ethylhexyl)-1,7-di(thiophen-2-yl)perylene-3,4,9,10-tetracarboxylic acid bisimide；7,18-bis(2-ethylhexyl)-11,22-dithiophen-2-yl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• CAS: 851786-19-1
• 化学式: C₄₈H₄₆N₂O₄S₂
• 分子量: 779.036
• InChiKey: SAHPZSAVAOLELM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-二(2-乙基己基)-1,7-二(噻吩-2-基)-3,4,9,10-苝四羧酸二酰亚胺 在 溴 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以95%的产率得到N,N'-di(2-ethylhexyl)-1,7-di(3,5dibromothiophen-2-yl)perylene-3,4,9,10-tetracarboxylic acid diimide
  参考文献：
  名称：

  Low Band Gap Thiophene−Perylene Diimide Systems with Tunable Charge Transport Properties

  摘要：

  Perylenediimide-pentathiophene systems with varied architecture of thiophene units were synthesized. The photophysical, electrochemical, and charge transport behavior of the synthesized compounds were studied. Both molecules showed a low band gap of similar to 1.4 eV. Surprisingly, the molecule with pentathiophene attached via beta-position to the PDI unit upon annealing showed a predominant hole mobility of 1 x 10(-4) cm(2) V-1 s(-1) whereas the compound with branched pentathiophene attached via beta-position showed an electron mobility of 9.8 x 10(-7) cm(2) V-1 s(-1). This suggests that charge transport properties can be tuned by simply varying the architecture of pentathiophene units.

  DOI：

  10.1021/ol1023486
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 四(三苯基膦)钯 、 硫酸 、 溴 、 potassium carbonate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 水 为溶剂， 反应 24.0h， 生成 N,N'-二(2-乙基己基)-1,7-二(噻吩-2-基)-3,4,9,10-苝四羧酸二酰亚胺
  参考文献：
  名称：

  Low Band Gap Thiophene−Perylene Diimide Systems with Tunable Charge Transport Properties

  摘要：

  Perylenediimide-pentathiophene systems with varied architecture of thiophene units were synthesized. The photophysical, electrochemical, and charge transport behavior of the synthesized compounds were studied. Both molecules showed a low band gap of similar to 1.4 eV. Surprisingly, the molecule with pentathiophene attached via beta-position to the PDI unit upon annealing showed a predominant hole mobility of 1 x 10(-4) cm(2) V-1 s(-1) whereas the compound with branched pentathiophene attached via beta-position showed an electron mobility of 9.8 x 10(-7) cm(2) V-1 s(-1). This suggests that charge transport properties can be tuned by simply varying the architecture of pentathiophene units.

  DOI：

  10.1021/ol1023486

文献信息

• Band gap and molecular energy level control of perylene diimide-based donor–acceptor copolymers for all-polymer solar cells
  作者：Erjun Zhou、Keisuke Tajima、Chunhe Yang、Kazuhito Hashimoto

  DOI：10.1039/b923452g

  日期：——

  Four types of perylene diimide-based electron acceptor materials, namely, poly[9,9-dioctylfluorene-2,7-diyl-alt-N,N′-di(2-ethylhexyl)-3,4,9,10-perylene diimide-1,7-diyl] (PF-PDI), poly[9,9-dioctylfluorene-2,7-diyl-alt-1,7-dithien-2-yl-N,N′-di(2-ethylhexyl)-3,4,9,10-perylene diimide-5′,5′′-diyl] (PF-DTPDI), polyN-[1-(2-ethylhexyl)-3-ethylheptanyl]-dithieno[3,2-b:2′,3′-d]pyrrole-2,6-diyl-alt-N,N′-di(2-ethylhexyl)-3,4,9,10-perylene diimide-1,7-diyl} (PDTP-PDI) and polyN-[1-(2-ethylhexyl)-3-ethylheptanyl]-dithieno[3,2-b:2′,3′-d]pyrrole-2,6-diyl-alt-1,7-dithien-2-yl-N,N′-di(2-ethylhexyl)-3,4,9,10-perylene diimide-5′,5′′-diyl} (PDTP-DTPDI), have been synthesized. By changing the donor segment from fluorene to dithienopyrrole and/or introducing a thiophene unit as a spacer, the band gap and energy levels of the resulting polymers could be tuned in a wide range. PDTP-DTPDI exhibited the narrowest band gap of 1.24 eV, and the absorption edge extended to 1 μm. All-polymer solar cells based on these electron acceptors, blended with different electron donor polymers, namely, a polythiophene derivative (P1) and a low band gap polymer (P2), were also investigated. P1:PDTP-PDI blends exhibited the highest power conversion efficiency of 0.93% under the illumination of AM 1.5 (100 mW cm−2). The monochromatic photocurrent response of the photovoltaic device based on P2:PDTP-PDI blends extended to the near-infrared region up to 1 μm.

  合成了四种基于苝二酰亚胺的电子受体材料，即聚[9,9-二辛基荧光素-2,7-二基-交替-N,N′-二(2-乙基己基)-3,4,9,10-苝二酰亚胺-1,7-二基]（PF-PDI）、聚[9,9-二辛基荧光素-2,7-二基-交替-1,7-二噻唑-2-基-N,N′-二(2-乙基己基)-3,4,9,10-苝二酰亚胺-5′,5′′-二基]（PF-DTPDI）、聚N-[1-(2-乙基己基)-3-乙基庚烷基]-二噻吩[3,2-b:2′,3′-d]吡咯-2,6-二基-交替-N,N′-二(2-乙基己基)-3,4,9,10-苝二酰亚胺-1,7-二基}（PDTP-PDI）和聚N-[1-(2-乙基己基)-3-乙基庚烷基]-二噻吩[3,2-b:2′,3′-d]吡咯-2,6-二基-交替-1,7-二噻唑-2-基-N,N′-二(2-乙基己基)-3,4,9,10-苝二酰亚胺-5′,5′′-二基}（PDTP-DTPDI）。通过将供体段从荧光素改为二噻吩吡咯和/或引入噻吩单元作为间隔，可以在较宽范围内调节所得聚合物的带隙和能级。PDTP-DTPDI展现出最窄的带隙为1.24 eV，吸收边缘延伸至1微米。这些电子受体与不同的电子供体聚合物（即聚噻吩衍生物P1和低带隙聚合物P2）混合后，构建了全聚合物太阳能电池。基于P1:PDTP-PDI混合物的电池在AM 1.5（100 mW cm⁻²）照射下展现出最高的光电转换效率为0.93%。基于P2:PDTP-PDI混合物的光伏器件的单色光光电流响应延伸至近红外区域，达到1微米。
• 一种高耐候性、可见光吸收与红外透明型染料及其合成方法与应用
  申请人：中国人民解放军军事科学院系统工程研究院

  公开号：CN116768894A

  公开（公告）日：2023-09-19

  本发明公开一种高耐候性、可见光吸收与红外透明型染料及其合成方法与应用，该合成方法以1，7‑二溴‑3，4，9，10‑苝四羧酸酐为原料，首先与2‑乙基己胺反应制备出N，N‑二(2‑乙基己基)‑1，7‑二溴‑3，4，9，10‑苝四羧酸二酰亚胺，然后与噻吩单体发生取代反应得到红外透明型染料的最终产物。该染料具有良好的耐光耐候性、耐热稳定性以及耐腐蚀性，同时兼具良好的可见光吸收与红外透明性能。将该类染料应用于可见光‑红外隐身伪装涂层中，所制备的涂层外观颜色与所配的标准色之间的色差值可控制在1.0以内，红外波段3～5μm发射率为0.42～0.48，8～14μm发射率为0.45～0.50。
• PERYLENE-BASED MATERIALS FOR ORGANIC PHOTOELECTRIC CONVERSION LAYERS
  申请人：Sony Corporation

  公开号：EP3126470B1

  公开（公告）日：2020-11-04
• US9978951B2
  申请人：——

  公开号：US9978951B2

  公开（公告）日：2018-05-22
• [EN] PERYLENE-BASED MATERIALS FOR ORGANIC PHOTOELECTRIC CONVERSION LAYERS<br/>[FR] MATÉRIAUX À BASE DE PÉRYLÈNE POUR DES COUCHES DE CONVERSION PHOTOÉLECTRIQUE
  申请人：SONY CORP

  公开号：WO2015150120A2

  公开（公告）日：2015-10-08

  The present disclosure relates to perylene-based molecules and their use in photoelectric conversion layer(s) and/or an organic or hybrid image sensor. The present disclosure also relates to absortion layer(s) and photoelectric conversion layer(s) comprising a molecule according to the present disclosure. The present disclosure also relates to a device, comprising a photoelectric conversion layer comprising at least one perylene-based molecule. Moreover, the present disclosure relates to an organic image sensor or a hybrid Silicon-organic image sensor comprising photoelectric conversion layer(s) according to the present disclosure.