1,6,9-tris(4-tert-butylphenoxy)-N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide | 524960-76-7

• 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: 1,6,9-tris(4-tert-butylphenoxy)-N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide
• 英文别名: 1,6,9-tris(4-tert-butylphenoxy)-N-(2,5-di-tert-butylphenyl)perylene-3, 4-dicarboxylic imide；5,12,20-Tris(4-tert-butylphenoxy)-16-(2,5-ditert-butylphenyl)-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2(23),3,5,7,9,11,13,18,21-decaene-15,17-dione
• CAS: 524960-76-7
• 化学式: C₆₆H₆₇NO₅
• 分子量: 954.262
• InChiKey: XXGDBYZHMBBCDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.2
• 重原子数：
  72
• 可旋转键数：
  12
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6,9-tris(4-tert-butylphenoxy)-N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide 在 氢氧化钾 、 溶剂黄146 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以81%的产率得到1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboxylic anhydride
  参考文献：
  名称：

  [EN] SYNTHESIS OF PERYLENE-PORPHYRIN BUILDING BLOCKS AND POLYMERS THEREOF FOR THE PRODUCTION OF LIGHT-HARVESTING ARRAYS
  [FR] SYNTHESE D'ELEMENTS CONSTITUTIFS A BASE DE PERYLENE-PORPHYRINE ET POLYMERES ASSOCIES DESTINES A LA PRODUCTION DE RESEAUX COLLECTEURS DE LUMIERE

  摘要：

  本发明提供了一种用于合成光收集阵列的方法、化合物和组合物，所述阵列包括：(a)包括第一电极的第一衬底；以及(b)与所述第一电极电性耦合的光收集棒层，其中每个所述光收集棒包括化学式(I)的聚合物：其中m至少为1；X1是一个电荷分离基团，X2至Xm+1是色素。X2至Xm+1中至少有一个与之耦合的苯菲啰基团。

  公开号：

  WO2003105237A1
• 作为产物：
  描述：

  2,5-二叔丁基苯胺 在 咪唑 、 zinc diacetate 、 溴 、 potassium carbonate 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 1,6,9-tris(4-tert-butylphenoxy)-N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide
  参考文献：
  名称：

  Practical synthesis of perylene-monoimide building blocks that possess features appropriate for use in porphyrin-based light-harvesting arrays

  摘要：

  Perylene-monoimide dyes with solubilizing aryloxy substituents at the perylene perimeter and a synthetic handle on the N-aryl group are valuable building blocks for incorporation as accessory pigments in porphyrin-based light-harvesting arrays. A family of such dyes has been prepared by reaction of 1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboxylic anhydride with a set of 4-iodo/ethynyl anilines (with or without 2,6-diisopropyl substituents) in the presence of Zn(OAc)(2)(.)2H(2)O in imidazole/mesitylene at 130degreesC. The workup procedures throughout the synthesis have been streamlined for scale-up purposes, minimizing chromatography. Two bis(perylene)porphyrin building blocks were prepared in a rational manner and examined in Sonogashira and Glaser polymerizations. The two isopropyl groups on the N-aryl group and the three 4-tert-butylphenoxy groups at the perylene perimeter are essential for high solubility of the bis(perylene)porphyrins and corresponding oligomers in organic solvents. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00020-6

文献信息

• Synthesis of perylene-porphyrin building blocks and polymers thereof for the production of light-harvesting arrays
  申请人：——

  公开号：US20030075216A1

  公开（公告）日：2003-04-24

  The present invention provides methods, compounds, and compositions for the synthesis of light harvesting arrays, such arrays comprising: (a) a first substrate comprising a first electrode; and (b) a layer of light harvesting rods electrically coupled to said first electrode, each of said light harvesting rods comprising a polymer of Formula I: X 1 &Parenopenst;X m+1 ) m (I) wherein m is at least 1; X 1 is a charge separation group, and X 2 through X m+1 are chromophores. At least one of X 2 through X m+1 has at least one perylene group coupled thereto.

  本发明提供了用于合成光收集阵列的方法、化合物和组合物，其中所述阵列包括：(a)第一基底，包括第一电极；以及(b)与所述第一电极电性耦合的光收集棒层，每个所述光收集棒包括式I：X1&Parenopenst;Xm+1)m(I)的聚合物，其中m至少为1；X1是一个电荷分离基团，X2至Xm+1是色团。X2至Xm+1中至少有一个与至少一个苝基团耦合。
• US6916982B2
  申请人：——

  公开号：US6916982B2

  公开（公告）日：2005-07-12
• [EN] SYNTHESIS OF PERYLENE-PORPHYRIN BUILDING BLOCKS AND POLYMERS THEREOF FOR THE PRODUCTION OF LIGHT-HARVESTING ARRAYS<br/>[FR] SYNTHESE D'ELEMENTS CONSTITUTIFS A BASE DE PERYLENE-PORPHYRINE ET POLYMERES ASSOCIES DESTINES A LA PRODUCTION DE RESEAUX COLLECTEURS DE LUMIERE
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2003105237A1

  公开（公告）日：2003-12-18

  The present invention provides methods, compounds, and compositions for the synthesis of light harvesting arrays, such arrays comprising: (a) a first substrate comprising a first electrode; and (b) a layer of light harvesting rods electrically coupled to said first electrode, each of said light harvesting rods comprising a polymer of Formula (I): wherein m is at least 1; X1 is a charge separation group, and X2 through Xm+1 are chromophores. At least one of X2 through Xm+1 has at least one perylene group coupled thereto.

  本发明提供了一种用于合成光收集阵列的方法、化合物和组合物，所述阵列包括：(a)包括第一电极的第一衬底；以及(b)与所述第一电极电性耦合的光收集棒层，其中每个所述光收集棒包括化学式(I)的聚合物：其中m至少为1；X1是一个电荷分离基团，X2至Xm+1是色素。X2至Xm+1中至少有一个与之耦合的苯菲啰基团。
• Practical synthesis of perylene-monoimide building blocks that possess features appropriate for use in porphyrin-based light-harvesting arrays
  作者：Kin-ya Tomizaki、Patchanita Thamyongkit、Robert S Loewe、Jonathan S Lindsey

  DOI：10.1016/s0040-4020(03)00020-6

  日期：2003.2

  Perylene-monoimide dyes with solubilizing aryloxy substituents at the perylene perimeter and a synthetic handle on the N-aryl group are valuable building blocks for incorporation as accessory pigments in porphyrin-based light-harvesting arrays. A family of such dyes has been prepared by reaction of 1,6,9-tris(4-tert-butylphenoxy)perylene-3,4-dicarboxylic anhydride with a set of 4-iodo/ethynyl anilines (with or without 2,6-diisopropyl substituents) in the presence of Zn(OAc)(2)(.)2H(2)O in imidazole/mesitylene at 130degreesC. The workup procedures throughout the synthesis have been streamlined for scale-up purposes, minimizing chromatography. Two bis(perylene)porphyrin building blocks were prepared in a rational manner and examined in Sonogashira and Glaser polymerizations. The two isopropyl groups on the N-aryl group and the three 4-tert-butylphenoxy groups at the perylene perimeter are essential for high solubility of the bis(perylene)porphyrins and corresponding oligomers in organic solvents. (C) 2003 Elsevier Science Ltd. All rights reserved.