N,N'-bis(2,6-diisopropylphenyl)-1,6-dibromoperylene-3,4:9,10-tetracarboximide | 861853-33-0

• 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(2,6-diisopropylphenyl)-1,6-dibromoperylene-3,4:9,10-tetracarboximide
• 英文别名: 11,26-Dibromo-7,18-bis[2,6-di(propan-2-yl)phenyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2(26),3,5(25),9,11,13,15,20(24),21-decaene-6,8,17,19-tetrone
• CAS: 861853-33-0
• 化学式: C₄₈H₄₀Br₂N₂O₄
• 分子量: 868.665
• InChiKey: COMDBUFFQJVJMS-UHFFFAOYSA-N

物化性质

• 密度：
  1.488±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  56
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 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'-bis(2,6-diisopropylphenyl)-1,6-dibromoperylene-3,4:9,10-tetracarboximide 、 1,7-二溴代苝二酰亚胺 、 三氟甲磺酸3-(三甲基硅基)-2-萘酯 在 cesium hydrogen fluoride 、 三(邻甲基苯基)磷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.25h， 以46%的产率得到N,N'-bis-(2,6-diisopropylphenyl)-3,4:9,10-dinaphtho-1,12:6,7-coronenetetracarboxdiimide
  参考文献：
  名称：

  Core-Extended Perylene Tetracarboxdiimides: The Homologous Series of Coronene Tetracarboxdiimides

  摘要：

  Two novel coronenedilmide (CDI) derivatives, CDI 2 and dinaphtho-CDI 4, were synthesized via straightforward synthetic routes completing the homologous series of coronene tetracarboxdlimides, which show remarkable optical properties with absorption wavelengths ranging from 380 to 600 nm, high absorption coefficients, and high fluorescence quantum yields.

  DOI：

  10.1021/ol201623f
• 作为产物：
  描述：

  2,6-二异丙基苯胺 、 3,4,9,10-苝四羧酸二酐 在 硫酸 、 溴 、 碘 、 N-甲基吡咯烷酮 、 溶剂黄146 作用下， 生成 N,N'-bis(2,6-diisopropylphenyl)-1,6-dibromoperylene-3,4:9,10-tetracarboximide 、 1,7-二溴代苝二酰亚胺
  参考文献：
  名称：

  1,6-二取代per双酰亚胺：简明合成和表征为近红外荧光染料

  摘要：

  报道了对bi二氢溴化物的溴化和随后的酰亚胺化的详细研究。以优化的高收率获得了1,6,7,12-四溴联苯二酰亚胺。另外，第一次以异构体纯的形式分离出1，6-二取代的区域异构体，并通过1 H NMR，MS，元素分析和光物理测量来确认结构。通过使用区域异构体1,6-和1,7-二溴-per双酰亚胺的混合物，合成，纯化1,6-二哌啶基per双酰亚胺（1,6-Piper-Pery），并在760的峰值处测量其荧光纳米 这些化合物可用作稳定的近红外吸收和荧光染料。

  DOI：

  10.1016/j.tetlet.2005.04.137

文献信息

• Coronene-Containing N-Heteroarenes: 13 Rings in a Row
  作者：Alexander H. Endres、Manuel Schaffroth、Fabian Paulus、Hilmar Reiss、Hubert Wadepohl、Frank Rominger、Roland Krämer、Uwe H. F. Bunz

  DOI：10.1021/jacs.5b12642

  日期：2016.2.17

  We describe the modular synthesis of three novel large N-heteroarenes, containing 9, 11, and 13 annulated rings. This modular system features fused azaacene units to a coronene nucleus. We evaluate the optical and electronic properties and the solid-state packing of the targets. The electronic properties of the 13-ring N-heteroarene allow the fabrication of a proof-of-concept thin-film transistor.

  我们描述了三种新型大 N-杂芳烃的模块化合成，其中包含 9、11 和 13 个环。这种模块化系统的特点是将氮杂并苯单元融合到冠烯核上。我们评估了目标的光学和电子特性以及固态包装。13 环 N-杂芳烃的电子特性允许制造概念验证薄膜晶体管。多晶薄膜的电子迁移率高达 8 × 10(-4) cm/(V s)。
• Multiple Chromophores Based on Rylene
  申请人：Konemann Martin

  公开号：US20080287678A1

  公开（公告）日：2008-11-20

  A rylene-based polychromophore of the general formula I in which the variables are each defined as follows: rylene is a radical of the formula which has been functionalized by at least one imide group, ester group or amide group and which may additionally be substituted by aryloxy, arylthio, hetaryloxy and/or hetarylthio; X is a rylenedicarboximide radical which absorbs at a different wavelength from the rylene radical, is bonded to the X radical in the peri-position via Y via a moiety —Y′-A-Y—, is bonded to the rylene radical and may likewise be substituted by aryloxy, arylthio, hetaryloxy and/or hetarylthio; A is a bridging member having at least one aromatic or heteroaromatic radical, the Y or Y and Y′ groups being bonded to the aromatic or heteroaromatic radical; Y is a moiety Y′ is a moiety where the moieties (i) and (ii) may be part of the ester groups of the rylene radical and the moieties (iii) are part of the imide groups of the rylene radical and the moieties (iv) are part of the amide groups of the rylene radical; R 1 is hydrogen or C 1 -C 18 -alkyl, where the R 1 radicals may be the same or different when they occur repeatedly; n is 1, 2 or 3; x is from 1 to 7.

  基于莱林的多色团的一般公式I，其中变量各自定义如下：莱林是一种具有下述结构的基团，已被至少一个酰亚胺基团、酯基团或酰胺基团官能化，并且还可以被芳氧基、芳硫基、杂芳氧基和/或杂芳硫基取代；X是一种莱林二酰亚胺基团，其在不同波长处吸收于莱林基团，通过Y通过一个团—Y′-A-Y—与X基团在邻位键合，与莱林基团键合，同样可以被芳氧基、芳硫基、杂芳氧基和/或杂芳硫基取代；A是至少具有一个芳香或杂芳基团的桥接成员，Y或Y和Y′基团与芳香或杂芳基团键合；Y是一个团，Y′是一个团，其中团（i）和（ii）可能是莱林基团的酯基团的一部分，团（iii）是莱林基团的酰亚胺基团的一部分，团（iv）是莱林基团的酰胺基团的一部分；R1是氢或C1-C18-烷基，当它们重复出现时，R1基团可能相同也可能不同；n为1、2或3；x为1到7。
• Substituted Rylene Derivatives
  申请人：Konemann Martin

  公开号：US20080167467A1

  公开（公告）日：2008-07-10

  Rylene derivatives of the general formula I in which the variables are each defined as follows: Rylene is a polycyclic conjugated ring system which comprises at least one perylene unit may comprise heteroatoms as ring atoms, may be functionalized by moieties comprising —CO— groups and/or may bear further substituents other than the A radicals; A is a radical of the formula X is oxygen or sulfur; R are identical or different radicals: optionally substituted alkyl, cycloalkyl, aryl, hetaryl, —U-aryl where U is an —O—, —S—, —NR 2 —, —CO—, —SO— or —SO 2 — moiety, or C 1 -C 12 -alkoxy, C 1 -C 6 -alkylthio, —C≡CR 2 , —CR 2 ═CR 2 2 , hydroxy, mercapto, halogen, cyano, nitro, —NR 3 R 4 , —NR 3 COR 4 , —CONR 3 R 4 , —SO 2 NR 3 R 4 , —COOR 3 or —SO 3 R 3 ; R′ are identical or different radicals: hydrogen or one of the R radicals; R 2 is hydrogen or alkyl, where the R 2 radicals may be the same or different when they occur more than once; R 3 , R 4 are each independently hydrogen; optionally substituted alkyl, aryl or hetaryl; n is from 1 to 8.

  该公式的Rylene衍生物为I，其中变量的定义如下： Rylene是一个多环共轭环系统，包括至少一个苝并单元，可能包含杂原子作为环原子，可能被含有—CO—基团的基团所官能化，或者可能带有除A基团以外的其他取代基； A是公式的基团； X是氧或硫； R是相同或不同的基团：可选取代的烷基、环烷基、芳基、杂芳基、—U-芳基，其中U是—O—、—S—、—NR2—、—CO—、—SO—或—SO2—基团，或C1-C12-烷氧基、C1-C6-烷基硫基、—C≡CR2、—CR2═CR22、羟基、巯基、卤素、氰基、硝基、—NR3R4、—NR3COR4、—CONR3R4、—SO2NR3R4、—COOR3或—SO3R3； R′是相同或不同的基团：氢或R基团之一； R2是氢或烷基，当它们出现多次时，R2基团可以相同或不同； R3、R4各自独立地为氢；可选取代的烷基、芳基或杂芳基； n为1至8。
• One-Pot Facile Synthesis of Pyridyl Annelated Perylene Bisimides
  作者：Wei Jiang、Yan Li、Wan Yue、Yonggang Zhen、Jianqiang Qu、Zhaohui Wang

  DOI：10.1021/ol902526t

  日期：2010.1.15

  Two regiospecifically pyridyl annelated perylene bisimides have been prepared in one pot by the combination of the Suzuki cross-coupling reaction and subsequent light-promoted cyclization In high yields.
• Synthesis and Optical Properties of Triphenylene-Based Dendritic Donor Perylene Diimide Acceptor Systems
  作者：Mahuya Bagui、Tanmoy Dutta、Sanjiban Chakraborty、Joseph S. Melinger、Haizhen Zhong、Andrew Keightley、Zhonghua Peng

  DOI：10.1021/jp1085334

  日期：2011.3.10

  A donor-acceptor charge transfer system based on two discotic mesogens has been synthesized. The donor is either a triphenylene (POG0) or a triphenylene-based conjugated dendron (POG1), while the acceptor is a perylene diimide (PDI) core. The donors are covalently linked to the bay positions of the PDI core through an ether linkage. In chloroform, due to the short donor-acceptor distance and the matching frontier orbital levels, photoinduced charge transfer from either the donor excitation or the acceptor excitation are both thermodynamically and kinetically favored, resulting in efficient quenching of both donor and acceptor fluorescence. In a less polar solvent, hexane, while charge transfer is still the dominant mechanism for decay of the excited electronic state of POG1, photo induced charge transfer is no longer energetically favorable for POG0 when the acceptor PDI core is excited, making the PDI core of POG0 weakly fluorescent in chloroform but strongly so in hexane. In solid film, POGO is highly aggregated through both PDI-PDI and triphenylene-triphenylene homotopic stacking. POG1, on the other hand, aggregates through triphenylene dendrons with limited PDI-PDI core stacking, presumably due to the steric hindrance caused by bulky triphenylene moieties which block the access to the PDI core. The efficient photoinduced charge transfer, coupled with the homotopic stacking that forms separated electron-transporting PDI-stacked columns and hole transporting triphenylene-stacked columns, suggests that the reported donor-acceptor systems based on dual-discotic mesogens are potentially new efficient photovoltaic materials.