2,5-Didodecyl-1,4-bis[5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]pyrrolo[3,4-c]pyrrole-3,6-dione | 1077629-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2,5-Didodecyl-1,4-bis[5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]pyrrolo[3,4-c]pyrrole-3,6-dione
• 英文别名: 2,5-didodecyl-1,4-bis[5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1077629-70-9
• 化学式: C₆₆H₈₈N₂O₂S₆
• 分子量: 1133.83
• InChiKey: NSTSDZRHEIKYBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.9
• 重原子数：
  76
• 可旋转键数：
  38
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  210
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-正己基噻吩 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 、 水 、 sodium carbonate 、 magnesium 作用下， 以 乙醚 、 氯仿 、 溶剂黄146 为溶剂， 反应 0.5h， 生成 2,5-Didodecyl-1,4-bis[5-[5-(5-hexylthiophen-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

文献信息

• [EN] SEMICONDUCTORS BASED ON DIKETOPYRROLOPYRROLES<br/>[FR] SEMI-CONDUCTEURS À BASE DE DICÉTOPYRROLOPYRROLES
  申请人：BASF SE

  公开号：WO2012041849A1

  公开（公告）日：2012-04-05

  The present invention relates to 1,4-diketopyrrolo[3,4-c]pyrrole (DPP) derivatives of the below formula (I) to their manufacture; to their use as organic semiconductors, e.g. in semiconductor devices, especially a sensor, a diode, a photodiode, an organic field effect transistor, a transistor for flexible displays, and/or a solar cell (photovoltaic cell); to such semiconductor devices comprising diketopyrrolopyrrol derivatives of the formula I as a semiconducting effective means, and to devices containing said semiconductor devices. The compounds of the formula I have excellent solubility in organic solvents. High efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when said compounds are used in semiconductor devices or organic photovoltaic (PV) devices.

  本发明涉及以下式(I)的1,4-二酮吡咯并[3,4-c]吡咯（DPP）衍生物的制造方法；它们作为有机半导体的用途，例如在半导体器件中，特别是传感器、二极管、光电二极管、有机场效应晶体管、柔性显示器件的晶体管和/或太阳能电池（光伏电池）中；将式I的二酮吡咯并吡咯衍生物作为半导体有效手段的半导体器件；以及包含该半导体器件的设备。式I的化合物在有机溶剂中具有优异的溶解性。当这些化合物用于半导体器件或有机光伏（PV）器件时，可以观察到高效的能量转换、优异的场效应迁移率、良好的开关电流比和/或优异的稳定性。
• SEMICONDUCTORS BASED ON DIKETOPYRROLOPYRROLES
  申请人：BASF SE

  公开号：EP2621927A1

  公开（公告）日：2013-08-07
• US8946376B2
  申请人：——

  公开号：US8946376B2

  公开（公告）日：2015-02-03
• 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.