2,5-dibenzyl-3,6-bis(4-chlorophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione | 331678-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2,5-dibenzyl-3,6-bis(4-chlorophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 2,5-dibenzyl-3,6-bis(4-chlorophenyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione；1,4-diketo-2,5-dibenzyl-3,6-di-(4'-chloro-phenyl)pyrrolo[3,4-c]pyrrole；1,4-diketo-2,5-dibenzyl-3,6-di-(4'-chlorophenyl)-pyrrolo[3,4-c]pyrrole；2,5-dibenzyl-1,4-bis(4-chlorophenyl)pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 331678-10-5
• 化学式: C₃₂H₂₂Cl₂N₂O₂
• 分子量: 537.445
• InChiKey: MUOVDHNKJITPMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  766.8±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-dibenzyl-3,6-bis(4-chlorophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 、 4-丁氧基苯硼酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 以93%的产率得到2,5-dibenzyl-3,6-bis(4'-butoxy-[1,1'-biphenyl]-4-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  Solid-state structure and optical properties of highly fluorescent diketopyrrolopyrrole derivatives synthesized by cross-coupling reaction

  摘要：

  Diketopyrrolopyrrole (DPP) derivatives with four different substituents were synthesized by cross-coupling reactions. The DPP derivatives were investigated in terms of their solid-state structure, absorption, emission, and electrochemistry. The electron-donating property of each substituent causes a redshift of UV/vis absorption and emission in the solution state. Although all of the DPP derivatives have high quantum yields in solution, only butoxyphenyl-substituted DPP exhibits strong emission in the solid state. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.067
• 作为产物：
  描述：

  溴甲苯 、 颜料红254 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到2,5-dibenzyl-3,6-bis(4-chlorophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Synthesis of highly fluorescent diketopyrrolopyrrole derivative and two-step response of fluorescence to acid

  摘要：

  A highly fluorescent diketopyrrolopyrrole derivative with amino groups was synthesized from Pigment Red 254 by a Pd-catalyzed amination reaction. The amino-substituted diketopyrrolopyrrole exhibits a two-step response Of fluorescence depending oil acidity. This optical property can be applied to a colorimetric detection of acids in the gas phase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.069

文献信息

• Fluorescent diketopyrrolopyrroles
  申请人：——

  公开号：US20030187106A1

  公开（公告）日：2003-10-02

  Fluorescent diketopyrrolopyrroles (“DPPs”) of the formula I 1 wherein R 1 and R 2 , independently from each other, stand for C 1 -C 25 -alkyl, allyl which can be substituted one to three times with C 1 -C 3 alkyl or Ar 3 , —CR 3 R 4 —(CH 2 ) m —Ar 3 , wherein R 3 and R 4 independently from each other stand for hydrogen or C 1 -C 4 alkyl, or phenyl which can be substituted on to three times with C 1 -C 3 alkyl, Ar 3 stands for phenyl or 1- or 2-naphthyl which can be substituted one to three times with C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen or phenyl, which can be substituted with C 1 -C 8 alkyl or C 1 -C 8 alkoxy one to three times, and m stands for 0, 1, 2, 3 or 4, and wherein C 1 -C 25 -alkyl or —CR 3 R 4 —(CH 2 ) m —Ar 3 , preferably C 1 -C 25 -alkyl, can be substituted with a functional group capable of increasing the solubility in water such as a tertiary amino group, —SO 3 − , or PO 4 2− , Ar 1 , and Ar 2 , independently from each other, stand for 2 wherein R 5 stands for C 1 -C 6 alkyl, —NR 8 R 9 , —OR 10 , —S(O) n R 8 , —Se(O) n R 8 , or phenyl, which can be substituted one to three times with C 1 -C 8 alkyl or C 1 -C 8 alkoxy, wherein R 8 and R 9 , independently from each other, stand for hydrogen, C 1 -C 25 -alkyl, C 5 -C 12 -cycloalkyl, —CR 3 R 4 —(CH 2 ) m —Ph, R 10 , wherein R 10 stands for C 6 -C 24 -aryl, or a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein Ph, the aryl and heterocyclic radical can be substituted one to three times with C 1 -C 8 alkyl, C 1 -C 8 alkoxy, or halogen, or R 8 and R 9 stand for —C(O)R 10 , wherein R 11 can be C 1 -C 25 -alkyl, C 5 -C 12 -cycloalkyl, R 10 , —OR 12 or —NR 13 R 14 , wherein R 12 , R 13 , and R 14 stand for C 1 -C 25 -alkyl, C 5 -C 12 -cycloalkyl, C 6 -C 24 -aryl, or a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the aryl and heterocyclic radical can be substituted one to three times with C 1 -C 8 alkyl or C 1 -C 8 alkoxy, or —NR 8 R 9 stands for a five- or sixmembered heterocyclic radical in which R 8 and R 9 together stand for tetramethylene, pentamethylene, —CH 2 —CH 2 —O—CH 2 —CH 2 —, or —CH 2 —CH 2 —NR 5 —CH 2 —CH 2 —, preferably —CH 2 —CH 2 —O—CH 2 —CH 2 —, and n stands for 0, 1, 2 or 3, and wherein R 6 and R 7 , independently from each other, stand for hydrogen or R 5 , but do not stand simultaneously for hydrogen, processes for its preparation, its uses and compositions comprising the compounds I.

  荧光二酮吡咯烷酮（“DPPs”）的公式I1，其中R1和R2，独立地代表C1-C25烷基，可以用C1-C3烷基或Ar3取代的丙烯基，—CR3R4—（CH2）m—Ar3，其中R3和R4独立地代表氢或C1-C4烷基，或苯基，可以用C1-C3烷基取代，Ar3代表苯基或1-或2-萘基，可以用C1-C8烷基，C1-C8烷氧基，卤素或苯基取代一至三次，m代表0、1、2、3或4，其中C1-C25烷基或—CR3R4—（CH2）m—Ar3，优选为C1-C25烷基，可以用增加水溶性的功能基团取代，例如三级胺基，—SO3−或PO42−，Ar1和Ar2独立地代表2，其中R5代表C1-C6烷基，—NR8R9，—OR10，—S（O）nR8，—Se（O）nR8或苯基，可以用C1-C8烷基或C1-C8烷氧基取代一至三次，其中R8和R9独立地代表氢，C1-C25烷基，C5-C12环烷基，—CR3R4—（CH2）m—Ph，其中R10代表C6-C24芳基，或由五至七个环原子组成的饱和或不饱和杂环基团，其中环由碳原子和从氮、氧和硫中选择的一至三个杂原子组成，其中Ph，芳基和杂环基团可以用C1-C8烷基，C1-C8烷氧基或卤素取代一至三次，或R8和R9代表—C（O）R10，其中R11可以是C1-C25烷基，C5-C12环烷基，R10，—OR12或—NR13R14，其中R12、R13和R14代表C1-C25烷基，C5-C12环烷基，C6-C24芳基，或由五至七个环原子组成的饱和或不饱和杂环基团，其中环由碳原子和从氮、氧和硫中选择的一至三个杂原子组成，其中芳基和杂环基团可以用C1-C8烷基或C1-C8烷氧基取代一至三次，或—NR8R9代表一个五元或六元杂环基团，其中R8和R9一起代表四亚甲基，五亚甲基，—CH2—CH2—O—CH2—CH2—或—CH2—CH2—NR5—CH2—CH2—，优选为—CH2—CH2—O—CH2—CH2—，n代表0、1、2或3，其中R6和R7独立地代表氢或R5，但不同时代表氢，其制备方法，其用途和包含化合物I的组合物。
• Electroluminescent devices comprising diketopyrrolopyrroles
  申请人：——

  公开号：US20040009368A1

  公开（公告）日：2004-01-15

  Electroluminescent device comprising in this order (a) an anode (b) a hole transporting layer (c) a light-emitting layer (d) optionally an electron transporting layer and (e) a cathode and a light-emitting substance, wherein the light-emitting substance is a diketopyrrolopyrrole represented by formula I or formula III 1 wherein R 1 and R 2 , independently from each other, stand for C 1 -C 25 -alkyl, allyl which can be substituted one to three times with C 1 -C 3 alkyl or Ar 3 , or —CR 3 R 4 —(CH 2 ) m —Ar 3 , wherein R 3 and R 4 independently from each other stand for hydrogen or C 1 -C 4 alkyl, or phenyl which can be substituted one to three times with C 1 -C 3 alkyl, Ar 3 stands for phenyl or 1- or 2-naphthyl which can be substituted one to three times with C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen or phenyl, which can be substituted with C 1 -C 8 alkyl or C 1 -C 8 alkoxy one to three times, and m stands for 0, 1, 2, 3 or 4, Ar 1 and Ar 2 , independently from each other, stand for aryl radicals, preferably for 2 3 wherein R 5 , R 6 and R 7 , independently from each other, stand for hydrogen, cyano, halogen, C 1 -C 6 alkyl, —NR 8 R 9 , —OR 10 , —S(O) n R 8 , —Se(O) n R 8 , or phenyl, which can be substituted one to three times with C 1 -C 8 alkyl or C 1 -C 8 alkoxy, wherein R 8 and R 9 , independently from each other, stand for hydrogen, phenyl, C 1 -C 25 -alkyl, C 5 -C 12 -cycloalkyl, —CR 3 R 4 —(CH 2 ) m -Ph, R 10 , wherein R 10 stands for C 6 -C 24 -aryl, or a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein Ph, the aryl and heterocyclic radical can be substituted one to three times with C 1 -C 8 alkyl, C 1 -C 8 alkoxy, or halogen, or R 8 and R 9 stand for —C(O)R 10 , wherein R 11 , can be C 1 -C 25 -alkyl, C 5 -C 12 -cycloalkyl, R 10 , —OR 12 or —NR 13 R 14 , wherein R 12 , R 13 , and R 14 stand for C 1 -C 25 -alkyl, C 5 -C 12 -cycloalkyl, C 6 -C 24 -aryl, or a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the aryl and heterocyclic radical can be substituted one to three times with C 1 -C 8 alkyl or C 1 -C 8 alkoxy, or —NR 8 R 9 stands for a five- or six membered heterocyclic radical in which R 8 and R 9 together stand for tetramethylene, pentamethylene, —CH 2 —CH 2 —O—CH 2 —CH 2 —, or —CH 2 —CH 2 —NR 5 —CH 2 —CH 2 —, preferably —CH 2 —CH 2 —O—CH 2 —CH 2 —, and n stands for 0, 1, 2 or 3, and wherein Z stands for a diradical selected from the group consisting of a single bond, C 2 -C 6 alkylene, which can be substituted one to three times with C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or phenyl, phenylene or naphthylene, processes for the preparation of compounds I, its uses and compositions comprising the compounds I and/or III.

  电致发光装置，包括以下组件：（a）阳极，（b）孔传输层，（c）发光层，（d）可选的电子传输层和（e）阴极，以及一种发光物质，其中该发光物质是由式I或式III1表示的二酮吡咯烷基吡咯烷衍生物，其中R1和R2独立地表示C1-C25烷基、可以用C1-C3烷基或Ar3取代一到三次的烯丙基，或—CR3R4—（CH2）m—Ar3，其中R3和R4独立地表示氢或C1-C4烷基，或可以用C1-C3烷基取代一到三次的苯基；Ar3表示可以用C1-C8烷基、C1-C8烷氧基、卤素或可以用C1-C8烷基或C1-C8烷氧基取代一到三次的苯基或1-或2-萘基；m表示0、1、2、3或4；Ar1和Ar2独立地表示芳基基团，优选为23，其中R5、R6和R7独立地表示氢、氰基、卤素、C1-C6烷基、—NR8R9、—OR10、—S（O）nR8、—Se（O）nR8或可以用C1-C8烷基或C1-C8烷氧基取代一到三次的苯基；其中R8和R9独立地表示氢、苯基、C1-C25烷基、C5-C12环烷基、—CR3R4—（CH2）m-Ph、R10，其中R10表示C6-C24芳基，或包含五到七个环原子的饱和或不饱和杂环基团，其中环由碳原子和从氮、氧和硫中选择的一到三个杂原子组成，其中Ph，芳基和杂环基团可以用C1-C8烷基、C1-C8烷氧基或卤素取代一到三次，或R8和R9表示—C（O）R10，其中R11可以是C1-C25烷基、C5-C12环烷基、R10、—OR12或—NR13R14，其中R12、R13和R14表示C1-C25烷基、C5-C12环烷基、C6-C24芳基或包含五到七个环原子的饱和或不饱和杂环基团，其中环由碳原子和从氮、氧和硫中选择的一到三个杂原子组成，其中芳基和杂环基团可以用C1-C8烷基或C1-C8烷氧基取代一到三次，或—NR8R9表示一个五元或六元杂环基团，在其中R8和R9一起表示四亚甲基、五亚甲基、—CH2—CH2—O—CH2—CH2—或—CH2—CH2—NR5—CH2—CH2—，优选为—CH2—CH2—O—CH2—CH2—，n表示0、1、2或3；其中Z表示从单键、可以用C1-C4烷基、C1-C4烷氧基或苯基取代一到三次的C2-C6烷基、苯基或萘基中选择的双基团，以及化合物I的制备方法、其用途以及包含化合物I和/或III的组合物。
• Impact of Systematic Structural Variation on the Energetics of π–π Stacking Interactions and Associated Computed Charge Transfer Integrals of Crystalline Diketopyrrolopyrroles
  作者：Jesus Calvo-Castro、Monika Warzecha、Alan R. Kennedy、Callum J. McHugh、Andrew J. McLean

  DOI：10.1021/cg5010165

  日期：2014.9.3

  Control over solid state structure is critical for effective performance in optoelectronic devices bearing if-conjugated charge mediating organic materials. A series of five structurally related N-benzyl-substituted diketopyrrolopyrroles (DPPs) differing solely in 2 out their 60 atoms were synthesized and crystal structures obtained. Systematic variation of the long axis aligned, pi-pi stacks has been identified within the single crystal structure series and intermolecular interaction energies and charge transfer integrals for the pi-pi stacks have been computed by means of density functional theory (M06-2X/6-311G(d)). The computed intermolecular interaction energies as well as charge transfer integrals were further investigated utilizing a series of systematically cropped dimer pairs, highlighting the crucial role of the benzyl/halo substitution on stabilization of these pi-pi dimers. Two of the DPPs, including a new polymorph of a previously reported structure exhibit twice the intermolecular interaction energy and comparable hole transfer integrals to Rubrene, one of the most efficient hole conducting materials known. The computed properties for all of the pi-pi dimer systems reported herein are consistent with trends predicted by a model system. As such these materials show great promise as charge mediators in organic electronic applications and may be exploited in systematic structure activity based investigations of charge transfer theory.
• US6603020B1
  申请人：——

  公开号：US6603020B1

  公开（公告）日：2003-08-05
• US7001677B2
  申请人：——

  公开号：US7001677B2

  公开（公告）日：2006-02-21