N,N'-dipropyl-1,6,7,12-tetrachloro-3,4:9,10-perylene 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'-dipropyl-1,6,7,12-tetrachloro-3,4:9,10-perylene diimide
• 英文别名: N,N'-bis-n-propyl-1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxdiimide；11,14,22,26-Tetrachloro-7,18-dipropyl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone
• 化学式: C₃₀H₁₈Cl₄N₂O₄
• 分子量: 612.296
• InChiKey: QXWQDPHDMBLBNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  N,N'-dipropyl-1,6,7,12-tetrachloro-3,4:9,10-perylene diimide 在 potassium carbonate 、 potassium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 水 、 异丙醇 为溶剂， 反应 30.0h， 生成 1,6,7,12-tetrakis(4-n-butyloxyphenoxy)perylene-3,4,9,10-tetracarboxylic acid dianhydride
  参考文献：
  名称：

  Synthesis and Optical Properties ofn-Type Polymers Containing Perylene Moieties

  摘要：

  Three n-type polymers, Ppe01, Ppe02, and Ppe03, containing both perylene moieties and fluorine atoms were synthesized. The synthesiszed polymeric perylene derivatives with good compatibility for solution processes were chosen as new acceptor candidates for substitution of C-60 derivatives in poly(3-hexylthiophene)-based organic photovoltaic application, by considering the results based on good thermal stability, high electron affinity ranging from 3.81 to 3.96 eV, absorption property in visible region, and effective photoluminescence quenching in the blend films with P3HT. The potential of the synthesized perylene polymers was investigated by measuring the current-voltage property of the polymeric P3HT: Ppe01 OPV device.

  DOI：

  10.1080/15421406.2010.497101
• 作为产物：
  描述：

  2,9-二丙基-蒽并2,1,9-def:6,5,10-d'e'f'二异喹啉-1,3,8,10-四酮 在 磺酰氯 、 碘苯 、 碘 作用下， 以 硝基苯 、 甲醇 为溶剂， 反应 20.0h， 以80%的产率得到N,N'-dipropyl-1,6,7,12-tetrachloro-3,4:9,10-perylene diimide
  参考文献：
  名称：

  Synthesis and Optical Properties ofn-Type Polymers Containing Perylene Moieties

  摘要：

  Three n-type polymers, Ppe01, Ppe02, and Ppe03, containing both perylene moieties and fluorine atoms were synthesized. The synthesiszed polymeric perylene derivatives with good compatibility for solution processes were chosen as new acceptor candidates for substitution of C-60 derivatives in poly(3-hexylthiophene)-based organic photovoltaic application, by considering the results based on good thermal stability, high electron affinity ranging from 3.81 to 3.96 eV, absorption property in visible region, and effective photoluminescence quenching in the blend films with P3HT. The potential of the synthesized perylene polymers was investigated by measuring the current-voltage property of the polymeric P3HT: Ppe01 OPV device.

  DOI：

  10.1080/15421406.2010.497101

文献信息

• Synthesis of novel multi-chromophoric soluble perylene derivatives and their photosensitizing properties with wide spectral response for SnO2 nanoporous electrode
  作者：He Tian、Pei-Hua Liu、Weihong Zhu、Enqin Gao、Da-Jun Wu、Sengmin Cai

  DOI：10.1039/b004063k

  日期：——

  Two series of new multi-chromophoric perylene-3,4:9,10-tetracarboxylic dianhydride dyes for solar cell sensitizers have been synthesized. One series consists of oxadiazole or naphthaldicarboximide that are linked with perylene units as N,N′-substituted chromophores. The other series has four substituents in the bay-region of the perylene core in addition to N,N′-substituents. These novel routes to highly efficient sensitizers for Grätzel-type solar cells avoid the complication of doping. A wide spectral photoresponse (from 310 to 700 nm) was observed with maximum IPCE (incident photon-to-current efficiency) of 24%. In addition, the sensitization is dependent on the energy match of the energy bands of the semiconductor and the redox potential of the segments in such assembled dyes.

  我们合成了两个系列的用于太阳能电池敏化剂的新型多色素过烯-3,4:9,10-四羧酸二酐染料。其中一个系列由噁二唑或萘二甲酰亚胺组成，与作为 N,N′-取代发色团的过烯单元相连。另一个系列除了 N,N′-取代基外，还在过烯烃核的畦区有四个取代基。这些用于格栅型太阳能电池的高效敏化剂的新路线避免了掺杂的复杂性。研究人员观察到了宽光谱光响应（从 310 纳米到 700 纳米），最大 IPCE（入射光子到电流的效率）为 24%。此外，敏化效果还取决于半导体能带的能量匹配以及这种组装染料中各段的氧化还原电位。
• HALOGEN-CONTAINING PERYLENETETRACARBOXYLIC ACID DERIVATIVES AND THE USE THEREOF
  申请人：Koenemann Martin

  公开号：US20110068328A1

  公开（公告）日：2011-03-24

  The invention relates to compounds of the formula (I) in which Y 1 and Y 2 are each O or, respectively, NR a or NR b , where R a and R b are each H or organyl; Z 1 to Z 4 are each O or S; R 11 to R 14 , R 21 to R 24 are each Cl, F; where 1 or 2 of the R 11 to R 14 , R 21 to R 24 radicals may also be CN and/or 1 R 11 to R 14 , R 21 to R 24 radical may be H; and where, when Y 1 is NR a , Z 1 or Z 2 may also be NR c , where R a and R c together are a bridging X group having from 2 to 5 atoms; and where, when Y 2 is NR b , Z 3 or Z 4 may also be NR d , where R b and R d together are a bridging X group having from 2 to 5 atoms; to a process for preparation thereof, and to their use as emitter materials, charge transport materials or exciton transport materials.

  该发明涉及以下式(I)的化合物，其中Y1和Y2分别为O或NRa或NRb，其中Ra和Rb分别为H或有机基；Z1至Z4分别为O或S；R11至R14，R21至R24分别为Cl，F；其中R11至R14，R21至R24中的1或2个基也可以是CN和/或1个R11至R14，R21至R24基可以是H；当Y1为NRa时，Z1或Z2也可以是NRc，其中Ra和Rc一起是具有2到5个原子的桥接X基团；当Y2为NRb时，Z3或Z4也可以是NRd，其中Rb和Rd一起是具有2到5个原子的桥接X基团；以及制备该化合物的方法，以及它们作为发射材料、电荷传输材料或激子传输材料的用途。
• 一类湾位苯氧基取代的苝酰亚胺荧光染料及其制备方法
  申请人：天津大学

  公开号：CN110003207A

  公开（公告）日：2019-07-12

  本发明涉及一类湾位苯氧基取代的苝酰亚胺荧光染料及其制备方法。类湾位苯氧基取代的苝酰亚胺荧光染料结构通式如下，通过正丙胺和氯代苝酸酐的缩合反应，提高了反应中间体氯代苝酰亚胺的溶解度。通过苯酚和氯代苝酰亚胺的亲核取代反应，获得了苯氧基取代的苝酰亚胺化合物。将湾位苯氧基修饰的苝酰亚胺水解得到湾位苯氧基修饰的苝酸酐。湾位苯氧基修饰的苝酸酐与三甲基苯胺或三亲水链苯胺缩合，得到最终苝酰亚胺类衍生物。本发明合成方法简单、易于操作、且具有相对较优的溶解性能。含有三亲水链的湾位苯氧基取代的苝酰亚胺染料具有聚集诱导发光行为，在光电和生物传感领域具有较大的应用前景。
• Synthesis of perylene-bridged bis(dibenzo-24-crown-8) and its assembly behavior with a fullerene-based secondary dibenzylammonium salt
  作者：HaiQing Yao、HengYi Zhang、Min Han、ZhiJun Ding、ZhiJun Zhang、Yu Liu

  DOI：10.1007/s11426-010-4066-0

  日期：2010.9

  This paper reports the synthesis of a perylene-bridged bis(crown ether) through the condensation reaction between primary amine-armed dibenzo-24-crown-8 and 3,4,9,10-perylenetetracarboxylic dianhydride. Pseudorotaxane with a perylene moiety at the wheel and a fullerene unit in the middle of the axle was prepared, which was evidenced by 1H NMR and fluorescence experiments. Subsequent investigations show that the formation and disassociation of the pseudorotaxane can be controlled by the alternating addition of KPF6 and 18-crown-6, following the change of the florescence intensity of perylene.

  本文报告了通过伯胺基二苯并-24-冠醚-8 与 3,4,9,10- 过烯四羧酸二酐的缩合反应合成过烯桥双冠醚的过程。通过 1H NMR 和荧光实验证明，制备出了车轮上有一个过烯分子、车轴中间有一个富勒烯单元的假紫杉烷。随后的研究表明，可以通过交替加入 KPF6 和 18-冠醚-6，根据过烯的荧光强度变化来控制假轴烷的形成和解离。
• METHOD FOR PRODUCING ORGANIC FIELD-EFFECT TRANSISTORS
  申请人：Koenemann Martin

  公开号：US20080017850A1

  公开（公告）日：2008-01-24

  A method for producing an organic field-effect transistor, comprising the steps of: a) providing a substrate comprising a gate structure, a source electrode and a drain electrode located on the substrate, and b) applying an n-type organic semiconducting compound to the area of the substrate where the gate structure, the source electrode and the drain electrode are located, wherein the n-type organic semiconducting compound is selected from the group consisting of compounds of the formula I wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, chlorine or bromine, with the proviso that at least one of these radicals is not hydrogen, Y 1 is O or NR a , wherein R a is hydrogen or an organyl residue, Y 2 is O or NR b , wherein R b is hydrogen or an organyl residue, Z 1 , Z 2 , Z 3 and Z 4 are O, where, in the case that Y 1 is NR a , one of the residues Z 1 and Z 2 may be a NR c group, where R a and R c together are a bridging group having 2 to 5 atoms between the terminal bonds, where, in the case that Y 2 is NR b , one of the residues Z 3 and Z 4 may be a NR d group, where R b and R d together are a bridging group having 2 to 5 atoms between the terminal bonds.