1-bromo-N,N'-bis(2,4-dimethylpent-3-yl)perylene-3,4:9,10-tetracarboxylic diimide | 946489-25-4

• 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-bromo-N,N'-bis(2,4-dimethylpent-3-yl)perylene-3,4:9,10-tetracarboxylic diimide
• 英文别名: 5-bromo-N,N’-bis(2,4-dimethylpent-3-yl)perylene-3,4:9,10-tetracarboxylicdiimides；1-bromo-N,N'-bis-(2,4-dimethyl-pent-3-yl)-perylene-3,4:9,10-tetracarboxylic acid diimide；11-Bromo-7,18-bis(2,4-dimethylpentan-3-yl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• CAS: 946489-25-4
• 化学式: C₃₈H₃₇BrN₂O₄
• 分子量: 665.627
• InChiKey: YJHARLPSPXDBDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-bromo-N,N'-bis(2,4-dimethylpent-3-yl)perylene-3,4:9,10-tetracarboxylic diimide 、 5,5'-双乙炔基-2,2'-联吡啶 在 bis(η3-allyl-μ-chloropalladium(II)) 、 三叔丁基膦 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以53%的产率得到11-[2-[6-[5-[2-[7,18-Bis(2,4-dimethylpentan-3-yl)-6,8,17,19-tetraoxo-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-11-yl]ethynyl]pyridin-2-yl]pyridin-3-yl]ethynyl]-7,18-bis(2,4-dimethylpentan-3-yl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
  参考文献：
  名称：

  WO2008/139452

  摘要：

  公开号：
• 作为产物：
  描述：

  N,N'-bis(2,4-dimethylpent-3-yl)perylene-3,4:9,10-tetracarboxylic bisimide 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以58%的产率得到1-bromo-N,N'-bis(2,4-dimethylpent-3-yl)perylene-3,4:9,10-tetracarboxylic diimide
  参考文献：
  名称：

  1,1'-联萘环化苝二酰亚胺：聚集诱导的发射增强和手性反转

  摘要：

  聚集诱导的发射增强和聚集诱导的手性反转是聚集体中对映体纯有机染料的两种单独现象。在这里，我们首次报道了这两个有趣的现象可以在对映体纯的S / R -1,1'-联萘环化苝二酰亚胺的聚集状态下同时观察到，其中两个苝二酰亚胺部分通过S / R桥接-1,1'-联萘酚 (BINOL) 在海湾位置。由于两个萘酚环化苝二酰亚胺部分之间的可旋转 C2 轴，它们都显示出聚集诱导的发射增强的内在行为。同时，由于酰亚胺和甲氧基位置的空间位阻，这两种独特的多环芳族酰亚胺在不良溶剂中相邻的两个π-体系优选采用交叉堆积模式，从而形成螺旋X-聚集体在圆二色性和圆偏振发光光谱研究中具有手性反转特征的相反手性（M / P）。

  DOI：

  10.1016/j.cclet.2021.11.069

文献信息

• Tuning the Electronic Nature of Mono-Bay Alkynyl-Phenyl-Substituted Perylene Bisimides: Synthesis, Structure, and Photophysical Properties
  作者：Ruchika Mishra、Jong Min Lim、Minjung Son、Piyush Panini、Dongho Kim、Jeyaraman Sankar

  DOI：10.1002/chem.201400099

  日期：2014.5.5

  Perylene bisimide (PBI) derivatives with various alkynyl–phenyl substituents at a single bay position have been synthesised by Sonogashira coupling. NMR spectroscopic studies reveal the unsymmetric nature of the dyads. All of the dyads undergo two reversible reductions, which demonstrates their structural and electrochemical rigidity. The synthesised dyads show a remarkable redshift in their absorption

  通过Sonogashira偶联合成了在单个间隔位置具有多个炔基-苯基取代基的双酰亚胺（PBI）衍生物。NMR光谱研究揭示了二重体的不对称性质。所有的二元组都经历了两个可逆的还原，这表明了它们的结构和电化学刚度。合成的二分体在其最大吸收和急剧的电子振动过程中显示出显着的红移。富含电子的取代基可促进电荷从取代基HOMO高效转移至缺电子的PBI核。带有强供电子乙炔基（二甲基氨基苯基）取代基的PBI表现出最有趣的光谱特征。该PBI的稳态特征显示吸收范围很广，几乎覆盖了整个可见光区域，没有任何发射。还证明了与乙炔基（二甲基氨基苯基）PBI的旋转运动有关的扭曲的分子内电荷转移（TICT）过程。计算研究揭示了各种取代基相对于PBI核的共面性。即使在单功能化之后，PBI芯本身也保持平坦，没有任何明显的变形。这说明，相对于双取代类似物，单官能化在间隔位置上产生了微不足道的空间位阻。尽管有先前关于1,7-二取
• Selective Imaging of Lipids in<i>Adipocytes</i>by Using an Imidazolyl Derivative of Perylene Bisimide
  作者：Ruchika Mishra、Zeeshan Mushtaq、Ramprasad Regar、Bhagaban Mallik、Vimlesh Kumar、Jeyaraman Sankar

  DOI：10.1002/cbic.201800134

  日期：2018.7.4

  Fat‐finding mission: A simple and neutral perylene bisimide with an imidazolyl side arm has been developed as a promising marker for the specific imaging of fat bodies in Drosophila and adipocytes in mammalian cells.

  寻肥任务：已开发出一种简单且中性的带有咪唑基侧臂的per双酰亚胺，作为果蝇脂肪体和哺乳动物细胞脂肪细胞特异性成像的有前途的标记。
• SELECTIVE BROMINATION OF PERYLENE DIIMIDES AND DERIVATIVES THEREOF UNDER MILD CONDITIONS
  申请人：Rybtchinski Boris

  公开号：US20100261901A1

  公开（公告）日：2010-10-14

  The present invention is directed to novel process for the preparation of regioselective perylenediimides derivatives, specifically mono and dibrominated derivatives.

  本发明涉及一种新型工艺，用于制备具有区域选择性的苝二酰亚胺衍生物，特别是单溴和双溴衍生物。
• Perylene diimides
  申请人：Yeda Research and Development Co. Ltd.

  公开号：EP2626359A1

  公开（公告）日：2013-08-14

  A perylene-diimide compound represented by the structure of formula 4: wherein R1 and R2 are the same or different comprising substituted or unsubstituted linear or branched alkyl group, substituted or unsubstituted saturated carbocyclic or heterocyclic ring or aryl; R3 is saturated or unsaturated heterocyclic ring; saturated or unsaturated carbocyclic ring, alkyl, alkylene, alkynyl, acetylene, diphenylacetylene, phenylacetylene, ethynyl-phenyl-2,2';6' 2" -terpyridine, 1,4-diethynylbenzene or Z-perylene ; and Z is 1,4 diethynylbenzene, phenyl, acetylene, aryl, cycloalkyl, heterocycle, olefin, azo, amide, C=N, N=C, carbonyl , 1,4 divinylbenzene, piperidine, 5,5'-Diethynyl-2,2'-Bipyridine dialcohol or dithiol; and optionally a metal or a metal ion is coordinated to said perylene diimide compound forming a metal complex with said compound.

  由式 4 结构代表的过烯二亚胺化合物： 其中 R1 和 R2 相同或不同，包括取代或未取代的直链或支链烷基、取代或未取代的饱和碳环或杂环或芳基； R3 是饱和或不饱和杂环、饱和或不饱和碳环、烷基、烯基、炔基、乙炔、二苯基乙炔、苯基乙炔、乙炔基苯基-2,2';6' 2" -三联吡啶、1,4-二炔基苯或 Z-珀烯；以及 Z 是 1,4-二乙炔基苯、苯基、炔基、芳基、环烷基、杂环、烯烃、偶氮、酰胺、C=N、N=C、羰基、1,4-二乙炔基苯、哌啶、5,5'-二乙炔基-2,2'-联吡啶二醇或二硫醇；以及 金属或金属离子与所述过二亚胺化合物配位，与所述化合物形成金属络合物。
• Selective Bromination of Perylene Diimides under Mild Conditions
  作者：Paramasivan Rajasingh、Revital Cohen、Elijah Shirman、Linda J. W. Shimon、Boris Rybtchinski

  DOI：10.1021/jo070367n

  日期：2007.8.1

  A novel method for the bromination of perylene diimides, PDI (1), under mild conditions is reported. Variation of the reaction conditions allows mono- and dibromination of PDIs to afford 2 and 3 (these can be separated through standard procedures) or exclusive dibromination to afford 3. Pure 1,7 regioisomers are obtained through repetitive crystallization. The structure of 1,7-3b was elucidated by a single-crystal X-ray analysis. The facility of the bromination reaction, which decreases in the order 1a > 1b > 1c, depends on PDI aggregation propensities. Monobrominated PDIs were utilized for the syntheses of novel unsymmetrical piperidinyl (4a and 4b) and trimethylsilylethynyl derivatives (5a and 5b). Computational studies (DFT) on imide substituent rotation in PDIs reveal that in the case of bulky groups there is a restricted rotation leading to isomers, in agreement with our experimental results. An aromatic core twist in PDIs bearing one and two bromine substituents was also investigated by DFT.