2,5-bis((S)-3,7-dimethyloctyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione | 1386439-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2,5-bis((S)-3,7-dimethyloctyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 英文别名: 2,5-bis[(S)-3,7-dimethyloctyl]-3,6-bis(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione；2,5-bis[(3S)-3,7-dimethyloctyl]-1,4-dithiophen-2-ylpyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1386439-80-0
• 化学式: C₃₄H₄₈N₂O₂S₂
• 分子量: 580.899
• InChiKey: ZIBLMZJEMUEJAR-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-bis((S)-3,7-dimethyloctyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 水 、 sodium carbonate 作用下， 以 氯仿 为溶剂， 反应 0.25h， 生成 2,5-bis[(3S)-3,7-dimethyloctyl]-1-[5-[5-[5-[(3S)-3,7-dimethyloctyl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-4-[5-[5-[5-[(3S)-3,7-dimethyloctyl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]pyrrolo[3,4-c]pyrrole-3,6-dione
  参考文献：
  名称：

  Optical Properties of Oligothiophene Substituted Diketopyrrolopyrrole Derivatives in the Solid Phase: Joint J- and H-Type Aggregation

  摘要：

  Photophysical properties of diketopyrrolopyrrole derivatives substituted with oligothiophenes are investigated. All compounds are found to be fluorescent both in solution and in the solid phase. At low temperature in the solid, fluorescence originates from excimer-like excited states. Comparison of absorption and fluorescence excitation spectra taken under matrix isolated conditions and on solid films show the presence of both J- and H-type absorption bands in the solid phase. Quantum-chemical calculations, including exciton-phonon coupling to account for deviations from the Born-Oppenheimer approximation, are performed to simulate the band shape of the lowest absorption band in the molecular solid. The joint presence of J- and H-bands is explained by the presence of two molecules in the unit cell. The Davydov splitting is substantial for molecules with linear alkyl substituents on the nitrogen atom (on the order of 0.2 eV) but can be reduced to almost zero by introducing branching at the beta-carbon of the alkyl side chain.

  DOI：

  10.1021/jp305097q
• 作为产物：
  描述：

  2-氰基噻吩 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 2-甲基-2-丁醇 、 乙腈 为溶剂， 反应 144.08h， 生成 2,5-bis((S)-3,7-dimethyloctyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  手性二酮吡咯并[3,4-c]吡咯基低聚噻吩：溶液和薄膜中聚集态的合成和表征

  摘要：

  在这项工作中，我们合成了三个结构相关的手性低聚噻吩家族，其中包含1,4-二酮-3,6-二芳基吡咯并[3,4-c]吡咯（DPP）单元作为中心核心；在内酰胺部分的氮原子上用相同的（ S ）-3,7-二甲基-1-辛基链进行官能化，它们仅在侧噻吩单元的数量上有所不同。这些π-共轭手性系统的聚集模式通过紫外-可见吸收和ECD光谱在溶液聚集（CHCl 3 /MeOH混合物）和薄膜条件下进行评估，特别描述了π-共轭长度的影响关于手性光学性质。有趣的是，我们发现连接到 DPP 核心的噻吩单元数量可变不仅影响聚集倾向，而且影响聚集体的螺旋性。 ECD 揭示了有关这些分子的超分子排列的信息，这是使用传统光谱学和显微镜技术无法获得的。薄膜样品揭示了与溶液聚集体截然不同的聚集模式，这使人们对后者可能作为前者的简单模型的普遍假设产生了怀疑。

  DOI：

  10.1002/chir.23608

文献信息

• Aggregation Modes of Chiral Diketopyrrolo[3,4‐ <i>c</i> ]pyrrole Dyes in Solution and Thin Films
  作者：Gianluigi Albano、Francesco Zinna、Francesco Urraci、Maria Annunziata M. Capozzi、Gennaro Pescitelli、Angela Punzi、Lorenzo Di Bari、Gianluca M. Farinola

  DOI：10.1002/chem.202201178

  日期：2022.9.12

  The aggregation modes of four new chiral diketopyrrolo[3,4-c]pyrrole (DPP) dyes, functionalized with enantiopure alkyl groups from natural sources, were deeply investigated in condition of solution aggregation and thin films by electronic circular dichroism (ECD) spectroscopy. ECD revealed superior capability, compared to absorbance spectroscopy, to provide information on the aggregation modes and

  通过电子圆二色性（ECD）光谱，深入研究了四种新型手性二酮吡咯并[3,4- c ]吡咯（DPP）染料的聚集模式，这些染料用天然来源的对映体纯烷基进行功能化。与吸收光谱相比，ECD 具有卓越的能力，可以提供有关聚集模式的信息并检测多种聚集途径可能共存的情况。
• Optical Properties of Oligothiophene Substituted Diketopyrrolopyrrole Derivatives in the Solid Phase: Joint J- and H-Type Aggregation
  作者：Mindaugas Kirkus、Linjun Wang、Sébastien Mothy、David Beljonne、Jérôme Cornil、René A. J. Janssen、Stefan C. J. Meskers

  DOI：10.1021/jp305097q

  日期：2012.8.2

  Photophysical properties of diketopyrrolopyrrole derivatives substituted with oligothiophenes are investigated. All compounds are found to be fluorescent both in solution and in the solid phase. At low temperature in the solid, fluorescence originates from excimer-like excited states. Comparison of absorption and fluorescence excitation spectra taken under matrix isolated conditions and on solid films show the presence of both J- and H-type absorption bands in the solid phase. Quantum-chemical calculations, including exciton-phonon coupling to account for deviations from the Born-Oppenheimer approximation, are performed to simulate the band shape of the lowest absorption band in the molecular solid. The joint presence of J- and H-bands is explained by the presence of two molecules in the unit cell. The Davydov splitting is substantial for molecules with linear alkyl substituents on the nitrogen atom (on the order of 0.2 eV) but can be reduced to almost zero by introducing branching at the beta-carbon of the alkyl side chain.
• Chiral diketopyrrolo[3,4‐<i>c</i>]pyrrole‐based oligothiophenes: Synthesis and characterization of aggregated states in solution and thin films
  作者：Gianluigi Albano、Laura Antonella Aronica、Gennaro Pescitelli、Lorenzo Di Bari

  DOI：10.1002/chir.23608

  日期：2024.1

  UV–Vis absorption and ECD spectroscopies in conditions of solution aggregation (CHCl3/MeOH mixtures) and as thin films, describing in particular the impact of the π-conjugation length on the chiroptical properties. Interestingly, we found that the variable number of thiophene units attached to the DPP core affects not only the propensity to aggregation but also the aggregates' helicity. ECD revealed information

  在这项工作中，我们合成了三个结构相关的手性低聚噻吩家族，其中包含1,4-二酮-3,6-二芳基吡咯并[3,4-c]吡咯（DPP）单元作为中心核心；在内酰胺部分的氮原子上用相同的（ S ）-3,7-二甲基-1-辛基链进行官能化，它们仅在侧噻吩单元的数量上有所不同。这些π-共轭手性系统的聚集模式通过紫外-可见吸收和ECD光谱在溶液聚集（CHCl 3 /MeOH混合物）和薄膜条件下进行评估，特别描述了π-共轭长度的影响关于手性光学性质。有趣的是，我们发现连接到 DPP 核心的噻吩单元数量可变不仅影响聚集倾向，而且影响聚集体的螺旋性。 ECD 揭示了有关这些分子的超分子排列的信息，这是使用传统光谱学和显微镜技术无法获得的。薄膜样品揭示了与溶液聚集体截然不同的聚集模式，这使人们对后者可能作为前者的简单模型的普遍假设产生了怀疑。