2-[3-cyano-4-(4-dibutylamino-phenyl)-5-oxo-1,5-dihydro-pyrrol-2-ylidene]-malononitrile | 113366-97-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[3-cyano-4-(4-dibutylamino-phenyl)-5-oxo-1,5-dihydro-pyrrol-2-ylidene]-malononitrile
• 英文别名: 3-[4-(dibutylamino)phenyl]-4-cyano-5-dicyanomethylene-2-oxo-3-pyrroline；3-(4-(N,N-di-n-butylamino)phenyl)-4-cyano-5-dicyanomethylidene-2-oxo-2,5-dihydropyrrole；2-[3-Cyano-4-[4-(dibutylamino)phenyl]-5-oxopyrrol-2-ylidene]propanedinitrile
• CAS: 113366-97-5
• 化学式: C₂₂H₂₃N₅O
• 分子量: 373.458
• InChiKey: JBAOEXGWBPLHDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-cyano-4-(4-dibutylamino-phenyl)-5-oxo-1,5-dihydro-pyrrol-2-ylidene]-malononitrile 、 乙基溴苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以87%的产率得到
  参考文献：
  名称：

  JP5686704

  摘要：

  公开号：
• 作为产物：
  描述：

  苯胺 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[3-cyano-4-(4-dibutylamino-phenyl)-5-oxo-1,5-dihydro-pyrrol-2-ylidene]-malononitrile
  参考文献：
  名称：

  Substituent modification of electro-optic chromophores with 4-cyano-5-dicyanomethylene-2,5-dihydro-1H-pyrrol-2-one as an acceptor

  摘要：

  Electro-optic chromophores with 4-cyano-5-dicyanomethylene-2,5-dihydro-1H-pyrrol-2-one (CDCOP) and aniline moieties as an acceptor and a donor, respectively, were synthesized with modification of three substituents, among which two were attached to the aniline moiety (R) and one was introduced to the CDCOP ring (R). Butyl and hexyl groups were introduced as R and R, and higher melting points were observed when R and R were the same. For the chromophore fixation, thermal crosslinking based on cyanate trimerization was performed. The chromophore with cyanate moiety in R was combined with bisphenol A dicyanate, and the thermal chromophore fixation was confirmed with almost no chromophore degradation.

  DOI：

  10.1080/15421406.2016.1200935

文献信息

• Near-Infrared Absorbing Merocyanine Dyes for Bulk Heterojunction Solar Cells
  作者：Hannah Bürckstümmer、Nils M. Kronenberg、Klaus Meerholz、Frank Würthner

  DOI：10.1021/ol101492q

  日期：2010.8.20

  A series of near-infrared absorbing merocyanine dyes bearing the strong electron-accepting 2-oxo-5-dicyanomethylene-pyrrolidine unit was synthesized and applied in combination with PC61BM and PC71BM in solution-processed photoactive layers of bulk heterojunction solar cells, exhibiting a remarkable performance range with power conversion efficiencies from 0.01% to 1.00%.

  合成了一系列带有强电子接受性2-氧代-5-二氰基亚甲基-吡咯烷单元的近红外吸收性花菁染料，并将其与PC 61 BM和PC 71 BM结合应用在本体异质结太阳能电池的溶液处理光敏层中，具有出色的性能范围，功率转换效率从0.01％到1.00％。
• DYE FOR PHOTOELECTRIC CONVERSION, SEMICONDUCTOR ELECTRODE, PHOTOELECTRIC CONVERSION ELEMENT, SOLAR CELL, AND NOVEL PYRROLINE-BASED COMPOUND
  申请人：Maeda Katsumi

  公开号：US20130118570A1

  公开（公告）日：2013-05-16

  Provided is a dye for photoelectric conversion containing at least one or more kind of a compound represented by the following General Formula (1) (in Formula (1), R 1 and R 2 represent any one of —CN, —SO 2 R, —COOR, and —CONR 2 (R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, or an aryl group); R 3 represents a direct bond or a substituted or unsubstituted alkylene group; X represents an acidic group; and D represents an organic group having an electron donating substituent or a substituted or unsubstituted heterocyclic group).

  提供一种用于光电转换的染料，其含有至少一种或多种由以下通式（1）表示的化合物（在式（1）中，R1和R2代表-CN、-SO2R、-COOR和-CONR2中的任意一种（其中R代表氢原子、取代或未取代的烷基、环烷基或芳基）；R3代表直接键或取代或未取代的烷基烯基；X代表酸性基团；D代表具有电子给体取代基或取代或未取代的杂环基团的有机基团）。
• MATUMOTO, HIROYUKI;IMAI, HIDENORI;TADA, SHOZI
  作者：MATUMOTO, HIROYUKI、IMAI, HIDENORI、TADA, SHOZI

  DOI：——

  日期：——
• MATSUMOTO, XIROYUKI;IMAI, XIDEHNORI
  作者：MATSUMOTO, XIROYUKI、IMAI, XIDEHNORI

  DOI：——

  日期：——
• DYES
  申请人：ZENECA LIMITED

  公开号：EP0667887A1

  公开（公告）日：1995-08-23