2,5-dibenzyl-3,6-bis(4-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione | 532952-72-0

• 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-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 英文别名: 2,5-Dibenzyl-1,4-bis(4-bromophenyl)pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 532952-72-0
• 化学式: C₃₂H₂₂Br₂N₂O₂
• 分子量: 626.347
• InChiKey: YKJYMAWHEKWYJW-UHFFFAOYSA-N

物化性质

• 熔点：
  388.5 °C
• 沸点：
  787.3±60.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 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-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 在 copper(l) iodide 、 sodium iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 125.0h， 以33%的产率得到2,5-dibenzyl-3,6-bis(4-iodophenyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione
  参考文献：
  名称：

  Impact of Systematic Structural Variation on the Energetics of π–π Stacking Interactions and Associated Computed Charge Transfer Integrals of Crystalline Diketopyrrolopyrroles

  摘要：

  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.

  DOI：

  10.1021/cg5010165
• 作为产物：
  描述：

  溴甲苯 、 3,6-bis(4-bromophenyl)-2,5-dihydropyrrolo[3, 4-c]pyrrole-1,4-dione 在 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以46 %的产率得到2,5-dibenzyl-3,6-bis(4-bromophenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  Chiral diketopyrrolopyrrolo dyes with light emission from solid and aggregated states

  摘要：

  由于二酮吡咯并[3,4-c]吡咯（DPP）衍生物在溶液中具有优异的发射特性，因此有望通过抑制聚集诱导的淬灭而在固态发射中显示出有趣的特征。在...

  DOI：

  10.1039/d3tc00308f

文献信息

• Detection of nitroaromatic vapours with diketopyrrolopyrrole thin films: exploring the role of structural order and morphology on thin film properties and fluorescence quenching efficiency
  作者：Monika Warzecha、Jesus Calvo-Castro、Alan R. Kennedy、Alisdair N. Macpherson、Kenneth Shankland、Norman Shankland、Andrew J. McLean、Callum J. McHugh

  DOI：10.1039/c4cc08468c

  日期：——

  Sensitive optical detection of nitroaromatic vapours with diketopyrrolopyrrole thin films is reported for the first time.

  第一次报道了使用二酮吡咯吡咯薄膜对硝基芳香蒸气进行敏感光学检测。
• A Highly Fluorescent σ‐Bonded Platinum(II) Diketopyrrolopyrrole Complex
  作者：Misaki Kamioka、Yitong Wang、Shigeki Mori、Hiroyuki Furuta、Soji Shimizu

  DOI：10.1002/ejic.202200081

  日期：2022.5.17

  Heavy, but fluorescent: A σ-bonded platinum(II) diketopyrrolopyrrole (Pt-DPP) complex was synthesized. The Pt-DPP complex exhibits intense DPP-centered fluorescence not only in solution but also in the solid state. The solid-state emission is ascribed to the well-segregated molecular packing, mitigating aggregation-caused quenching. The unique fluorescence properties are beneficial for creating DPP-based

  重，但荧光：合成了 σ 键合铂 (II) 二酮吡咯并吡咯 (Pt-DPP) 配合物。Pt-DPP 复合物不仅在溶液中而且在固态下都表现出强烈的以 DPP 为中心的荧光。固态发射归因于良好分离的分子堆积，减轻了聚集引起的猝灭。独特的荧光特性有利于创建基于 DPP 的功能性发色团。
• Substituted Diketopyrrolopyrroles as Input Energy Units in Soluble Donor-Acceptor Dyads
  作者：Delphine Hablot、Pascal Retailleau、Raymond Ziessel

  DOI：10.1002/chem.201001953

  日期：2010.12.3

  Dual for a transfer! A strategy has been devised for functionalizing fluorescent diketopyrrolopyrroles (DPP) dyes with a borondipyromethene (BODIPY) unit acting as an energy acceptor (see scheme). Quantitative intramolecular electronic energy transfer is effective by excitation in the DPP subunit in apolar and polar media, including aqueous methanol, to provide large Stoke shifts.

  双重转让！已经设计出一种策略，用于将双二吡咯亚甲基（BODIPY）单元用作能量受体来官能化荧光二酮吡咯并吡咯（DPP）染料（请参见方案）。通过在非极性和极性介质（包括甲醇水溶液）中的DPP亚基中激发，可以进行定量的分子内电子能量转移，以提供较大的斯托克频移。
• Metal-Free and Fluorescent Diketopyrrolopyrrole Fluorophores for Dye-Sensitized Solar Cells
  作者：Delphine Hablot、Ashraful Islam、Liyuan Han、Raymond Ziessel

  DOI：10.1002/cplu.201200059

  日期：2012.6

  the phenyl‐ or thiophene‐based DPP dyes. The fluorescence spectra also display broad bands at 555 nm (ΦF=0.57 and τF=4.6 ns) for the phenyl‐ and at 624 nm (ΦF=0.31 and τF=3.5 ns) for the thiophene‐based molecular structures. Under standard global AM 1.5G irradiation a maximum photon‐to‐electron conversion efficiency of 2.54 % was achieved with dye‐sensitized solar cells based on nanocrystalline TiO2

  设计并合成了新型无金属和荧光二吡咯并吡咯（DPP）染料，该染料由带有中心双（内酰胺）的侧基苄基或支链烃基作为增溶片段和两个正交侧臂（二甲基氨基丙炔和苯甲酸酯阴离子）组成。对于苯基或噻吩基DPP染料，记录在THF中的UV / Vis吸收光谱主要集中在488 nm或602 nm处强烈的低能量π-π*吸收。的荧光光谱也在555nm处显示宽频带（Φ ˚F = 0.57和τ ˚F为苯基，并在624纳米（= 4.6纳秒）Φ ˚F = 0.31和τ ˚F= 3.5 ns），基于噻吩的分子结构。在标准的全球AM 1.5G辐射下，基于纳米晶TiO 2的染料敏化太阳能电池（J sc = 7.5 mA cm -2，V oc = 0.49 V和FF）实现的最大光电子转换效率为2.54％苯基基DPP染料为= 0.70），噻吩基DPP染料为1.89％（J sc = 7.1 mA cm -2，V oc = 0.41 V和FF
• Using a Photoacid Generator to Switch the Direction of Electronic Energy Transfer in a Molecular Triad
  作者：Delphine Hablot、Anthony Harriman、Raymond Ziessel

  DOI：10.1002/anie.201102065

  日期：2011.8.16

  A switch in time: A sequence of highly efficient, intramolecular electronic energy transfer steps follows from selective illumination of the fluorescent center (DPP) present in a new class of molecular triads (see picture). The direction of energy flow depends on the protonation state of one of the termini (B and G), which can be modulated by direct or sensitized photolysis of a photoacid generator

  时间的转换：一系列新型高效的分子内电子能量转移步骤来自对新型分子三元组中存在的荧光中心（DPP）的选择性照明。能量流的方向取决于一个末端（B和G）的质子化状态，该质子化状态可以通过光酸产生剂（PAG）的直接或敏化光解进行调节。