N,N'-dicyclohexyl-1-bromo-7-pyrrolidinylperylene-3,4:9,10-tetracarboxylic acid bisimide | 249733-90-2

• 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: N,N'-dicyclohexyl-1-bromo-7-pyrrolidinylperylene-3,4:9,10-tetracarboxylic acid bisimide
• 英文别名: 1-(N-pyrrolidinyl)-7-bromo-N,N'-dicyclohexyl-3,4:9,10-perylenebis(dicarboximide)；11-Bromo-7,18-dicyclohexyl-22-pyrrolidin-1-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: 249733-90-2
• 化学式: C₄₀H₃₆BrN₃O₄
• 分子量: 702.648
• InChiKey: MBSYVLXFFNBFPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  48
• 可旋转键数：
  3
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氰化锌 、 N,N'-dicyclohexyl-1-bromo-7-pyrrolidinylperylene-3,4:9,10-tetracarboxylic acid bisimide 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以84%的产率得到N,N'-dicyclohexyl-1-cyano-7-pyrrolidinylperylene-3,4:9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes

  摘要：

  A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylenE! bisimides are presumably contaminated with the respective 1,6 regioisomers. N,N'-Dicyclohexyl- 1,7-dibromoperylene bisimide 1, 7-3 is obtained for the first time in isomerically pure form, and its structure is unequivocally confirmed by X-ray analysis. By using regioisomerically pure l,'7-dibromoperylene bisimide 1,7-3, 1,7-dipyrrolidinylperylene bisimides 4a-c and 1,7-dipyrrolidinylperylene bisanhydride 5 as well as the unsymmetrically difunctionalized 1-bromo7-pyrrolidinyl- and 1-cyano-7-pyrrolidinylperylene bisimides 7 and 8 are synthesized in good yield.

  DOI：

  10.1021/jo048880d
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 硫酸 、 溴 、 碘 作用下， 反应 52.0h， 生成 N,N'-dicyclohexyl-1-bromo-7-pyrrolidinylperylene-3,4:9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes

  摘要：

  A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylenE! bisimides are presumably contaminated with the respective 1,6 regioisomers. N,N'-Dicyclohexyl- 1,7-dibromoperylene bisimide 1, 7-3 is obtained for the first time in isomerically pure form, and its structure is unequivocally confirmed by X-ray analysis. By using regioisomerically pure l,'7-dibromoperylene bisimide 1,7-3, 1,7-dipyrrolidinylperylene bisimides 4a-c and 1,7-dipyrrolidinylperylene bisanhydride 5 as well as the unsymmetrically difunctionalized 1-bromo7-pyrrolidinyl- and 1-cyano-7-pyrrolidinylperylene bisimides 7 and 8 are synthesized in good yield.

  DOI：

  10.1021/jo048880d

文献信息

• 3,4:9,10-Perylenebis(dicarboximide) chromophores that function as both electron donors and acceptors
  作者：Yongyu Zhao、Michael R. Wasielewski

  DOI：10.1016/s0040-4039(99)01468-9

  日期：1999.9

  Five green 3,4:9,10-perylenebis(dicarboximide) dyes that both donate and accept electrons have been synthesized under mild conditions in high yields. These chromophores undergo reversible one-electron oxidation and reduction in butyronitrile at modest potentials. (C) 1999 Elsevier Science Ltd. All rights reserved.