N,N'-bis((S)-1-phenylethyl)perylene-3,4,9,10-tetracarboxylic diimide

• 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'-bis((S)-1-phenylethyl)perylene-3,4,9,10-tetracarboxylic diimide
• 英文别名: N,N'-bis((S)-(-)-1-phenylethyl)-3,4,9,10-perylenebis(dicarboximide)；2,9-bis((S)-1-phenylethyl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone；(S,S)-N,N'-bis(1-phenylethyl)perylene-3,4,9,10-tetracarboxylic diimide；7,18-bis[(1S)-1-phenylethyl]-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
• 化学式: C₄₀H₂₆N₂O₄
• 分子量: 598.657
• InChiKey: FRHVWQAXNHAVFZ-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  46
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 3,4,9,10-苝四羧酸二酐 在 zinc(II) acetate dihydrate 作用下， 反应 4.0h， 以76%的产率得到N,N'-bis((S)-1-phenylethyl)perylene-3,4,9,10-tetracarboxylic diimide
  参考文献：
  名称：

  Solid-state AIEnh-circularly polarised luminescence of chiral perylene diimide fluorophores

  摘要：

  手性 N,N′-双（1-苯基乙基）过烯-3,4,9,10-四羧酸二亚胺（BPP）在 KBr、PMMA 和 myo-IPU 基质中表现出固态聚集诱导的增强圆偏振发光（AIEnh-CPL）。

  DOI：

  10.1039/c8ra09785b

文献信息

• Greener Dye Synthesis: Continuous, Solvent‐Free Synthesis of Commodity Perylene Diimides by Twin‐Screw Extrusion
  作者：Qun Cao、Deborah E. Crawford、Chengcheng Shi、Stuart L. James

  DOI：10.1002/anie.201913625

  日期：2020.3.9

  synthesis of more difficult aniline-derived PDIs. Furthermore, an automated continuous TSE process for Pigments Black 31 and 32 is demonstrated, with a throughput rate of about 1500 g day-1 , corresponding to a space time yield of about 30×103  kg m-3  day-1 , which is 1-2 orders of magnitude greater than for solvent-based batch methods. These methods provide substantial waste reductions and improved

  报道了一种使用双螺杆挤出（TSE）合成各种萘酰亚胺和di二酰亚胺（PDI）的连续，可扩展且无溶剂的方法。使用TSE，无需过量的胺反应物或产物纯化即可定量获得萘酰亚胺。具有良好的官能团耐受性，以50-99％的产率获得了烷基和苄胺衍生的PDI（包括商业染料）。使用K2 CO3可以合成更困难的苯胺衍生PDI。此外，展示了用于颜料黑31和32的自动化连续TSE工艺，其吞吐速率约为1500 g day-1，对应于约30×103 kg m-3 day-1的时空产量，即1比基于溶剂的批处理方法大-2个数量级。
• Swallow tail bay-substituted novel perylene bisimides: Synthesis, characterization, photophysical and electrochemical properties and DFT studies
  作者：Basma Al-Khateeb、Meltem Dinleyici、Arwa Abourajab、Cansu Kök、Jagadeesh B. Bodapati、Duygu Uzun、Sermet Koyuncu、Huriye Icil

  DOI：10.1016/j.jphotochem.2020.112432

  日期：2020.4

  bay-substituted perylene bisanhydride (6) and two bay-substituted perylene bisimides (7, 10) have been successfully synthesized with a large and swallow tail type, 2-decyl-1-tetradecanoyl substituents at the bay area (1 and 7 positions). The non-bay-substituted perylene bisimides with the same N-substituents were prepared as model compounds (3, 9) for comparison. Absorption and fluorescence, electrochemical, s

  新颖，一个托架，取代的苝二酐（6）和两个托架取代的苝二酰亚胺（7，10）已经被成功地与在隔舱区大和燕尾型，2-癸基-1-十四酰基取代基的合成（1和7个职位）。具有相同的N-取代基的非托架取代的二萘嵌苯双酰亚胺制备成模型化合物（3，9用于比较）。研究了化合物的吸收和荧光，电化学，光谱电化学，形态学性质，然后进行了密度泛函理论（DFT）的模拟。化合物6，7和10已显示J聚集在UV-vis-NIR区域无特征，非常宽的吸收，并具有强大的荧光猝灭作用，这归因于分子内电子从电子供体2-癸基-1-十四烷酰基取代基到PDI受体和支架的有效分子内转移，从而使π-π分子间相互作用，诱导分子聚集。LUMO和HOMO值的绝对位置3，9，6，7和10在溶液是-3.91 / -6.09电子伏特，-3.93 / -6.08电子伏特，-4.02 / -5.90电子伏特，-4.02 / -5.91 eV和-分别为4.02 /
• Chiral imides as potential chiroptical switches: synthesis and optical properties
  作者：Erin K. Todd、Sheng Wang、Xinhua Wan、Zhi Yuan Wang

  DOI：10.1016/j.tetlet.2004.11.147

  日期：2005.1

  A series of chiral aromatic imides and diimides were synthesized and their electrochemical, absorption, fluorescent, and chiroptical properties were examined for their potential application as molecular chiroptical switches. These compounds exhibit strong UV-vis absorptions, and can be electrochemically reduced to radical anions that absorb in the near infrared (NIR) region. Further reduction to the dianionic states results in new absorptions in the visible region. The changes in circular dichroism upon redox switching were apparent in the UV-vis region but were absent in the NIR region. (C) 2004 Elsevier Ltd. All rights reserved.