1,6,9-tribromo-N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide | 358762-70-6

• 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-tribromo-N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide
• 英文别名: N-(2,5-di-tert-butyl-phenyl)-1,6,9-tribromoperylene-3,4-dicarboximide；1,6,9-tribromo-N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboxylic imide；5,12,20-Tribromo-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: 358762-70-6
• 化学式: C₃₆H₂₈Br₃NO₂
• 分子量: 746.336
• InChiKey: LQBXTHFURIIXAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6,9-tribromo-N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide 在 氢氧化钾 、 copper(l) iodide 作用下， 以 N-甲基吡咯烷酮 、 乙酸乙酯 、 甲苯 、 叔丁醇 为溶剂， 反应 28.5h， 生成 N-(amino)-1,6-bis-(3,5-di-tert-butylphenoxy)-9-(N-pyrrolidinyl)perylene-3,4-dicarboximide
  参考文献：
  名称：

  Photorefractivity in Nematic Liquid Crystals Using a Donor−Acceptor Dyad with a Low-Lying Excited Singlet State for Charge Generation

  摘要：

  The photorefractive effect was observed in room-temperature nematic liquid crystal composites consisting of a eutectic mixture of 65% 4 '-(n-pentyl)-4-cyanobiphenyl and 35% 4 '-(n-octyloxy)-4-cyanobiphenyl doped with a donor-acceptor dyad in which 9-(N-pyrrolidinyl)perylene-3,4-dicarboximide is directly linked to 1,8: 4,5-naphthalenetetracarboxydiimide. This dyad has a broad, intense absorption band that extends from 500 to 750 nm. Measurements of two-beam asymmetric energy exchange (beam-coupling) and the diffraction efficiency of the refractive index grating produced in these liquid crystal thin films were carried out. A comparison is made between the covalent donor-acceptor dyad and the corresponding noncovalent donor-acceptor pair. In each case the covalent dyad outperforms the noncovalent donor-acceptor pair. The results show that aminoaryleneimides are promising new charge donating chromophores that are capable of extending photorefractive performance of nematic liquid crystal composites into the near-infrared region of the spectrum.

  DOI：

  10.1021/jp011561v
• 作为产物：
  描述：

  2,5-二叔丁基苯胺 在 咪唑 、 zinc diacetate 、 溴 作用下， 以 氯仿 、 水 为溶剂， 反应 41.0h， 生成 1,6,9-tribromo-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

• [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。
• Perylene n-type semiconductors and related devices
  申请人：Marks J. Tobin

  公开号：US20050176970A1

  公开（公告）日：2005-08-11

  Mono- and diimide perylene and naphthalene compounds, N- and core-substituted with electron-withdrawing groups, for use in the fabrication of various device structures.

  单亚胺和二亚胺苝和萘化合物，N-和核取代为电子受体基团，用于制备各种器件结构。
• Solvatochromic rotaxane molecular shuttles
  作者：Duygu Deniz Günbaş、Leszek Zalewski、Albert M. Brouwer

  DOI：10.1039/c0cc05755j

  日期：——

  A strongly fluorescent bistable rotaxane is described in which the relative position of the macrocyclic ring with respect to a solvatochromic fluorophore gives a strong response in the spectral domain.

  描述了一种强荧光双稳态轮烷，其中大环相对于溶色荧光团的相对位置会在光谱域产生强烈反应。
• Substituent Effects for Perylenedicarboxylic Anhydrides on the Performance of Dye-sensitized Solar Cells: The Simpler, the Better
  作者：Joe Otsuki、Yusho Takaguchi、Daichi Takahashi、Kosuke Sugawa、Palanisamy Kalimuthu、Ashraful Islam、Liyuan Han

  DOI：10.1246/cl.130073

  日期：2013.4.5

  The effects of substituents at the bay positions for push–pull-type perylenedicarboxylic anhydride dyes on the performance of dye-sensitized solar cells were investigated. The substituents fine-tune the optical and redox properties of the dyes. It turned out that the simplest dye without any substituent results in highest-efficiency cells because of its broadened IPCE spectrum due to intermolecular interactions, which implies that aggregation may not always be detrimental to the performance of the solar cell.

  研究了推拉型过二羧酸酐染料的畦位取代基对染料敏化太阳能电池性能的影响。取代基对染料的光学和氧化还原特性进行了微调。结果表明，不含任何取代基的最简单染料由于分子间相互作用而拓宽了 IPCE 光谱，因此能产生最高效率的电池，这意味着聚集并不总是不利于太阳能电池的性能。
• 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。