1,1'-ethynyl-bis[N,N'-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide] | 1174418-78-0

• 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: 1,1'-ethynyl-bis[N,N'-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide]
• 英文别名: 11-[2-[6,8,17,19-Tetraoxo-7,18-di(tridecan-7-yl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-11-yl]ethynyl]-7,18-di(tridecan-7-yl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone；11-[2-[6,8,17,19-tetraoxo-7,18-di(tridecan-7-yl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-11-yl]ethynyl]-7,18-di(tridecan-7-yl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• CAS: 1174418-78-0
• 化学式: C₁₀₂H₁₂₂N₄O₈
• 分子量: 1532.11
• InChiKey: LQDVZDRUPBPPBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  30.8
• 重原子数：
  114
• 可旋转键数：
  46
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-acetylene-N,N’-bis(1-hexylheptyl)perylene-3,4:9,10-tetracarboxylicdiimide 、 1-bromo-N,N'-bis(1-hexylheptyl)perylene-3,4:9,10-bis(dicarboximide) 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以76%的产率得到1,1'-ethynyl-bis[N,N'-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide]
  参考文献：
  名称：

  共轭二聚和三聚Per二酰亚胺低聚物

  摘要：

  制备了包括per二酰亚胺单元的二聚和三聚分子，所述per二酰亚胺单元通过亚乙基，亚乙炔基或丁二亚炔基间隔物经由间隔位置共轭连接。电化学和光物理特征表明，与单体相比，通过C-C三键连接的低聚物可有效降低LUMO。分子建模证实，CC三键实现了边界轨道的有效离域，而亚苯基在扩展共轭方面的能力较弱，这部分是由于空间相互作用所致。

  DOI：

  10.1021/ol9012734

文献信息

• Conjugated Dimeric and Trimeric Perylenediimide Oligomers
  作者：Qifan Yan、Dahui Zhao

  DOI：10.1021/ol9012734

  日期：2009.8.6

  conjugatively linked by phenylene, ethynylene, or a butadiynylene spacer via the bay positions were prepared. Electrochemical and photophysical characterizations showed that oligomers connected by C−C triple bond(s) exhibited effectively lowered LUMO compared to the monomer. Molecular modeling confirmed that the C−C triple bond realized efficient delocalization of frontier orbitals, while phenylene was less competent

  制备了包括per二酰亚胺单元的二聚和三聚分子，所述per二酰亚胺单元通过亚乙基，亚乙炔基或丁二亚炔基间隔物经由间隔位置共轭连接。电化学和光物理特征表明，与单体相比，通过C-C三键连接的低聚物可有效降低LUMO。分子建模证实，CC三键实现了边界轨道的有效离域，而亚苯基在扩展共轭方面的能力较弱，这部分是由于空间相互作用所致。
• Structural Refinement of Ladder-Type Perylenediimide Dimers: A Classical Tale of Conformational Dynamics
  作者：Mykhaylo Myahkostupov、Valentina Prusakova、Daniel G. Oblinsky、Gregory D. Scholes、Felix N. Castellano

  DOI：10.1021/jo401348w

  日期：2013.9.6

  We have synthesized and thoroughly characterized two representative ladder-type acetylene-bridged perylenediimide dimers bearing long alkyl chain solubilizing groups, bis[1-ethynyl-N,N'-bis (1-hexylheptyl)-perylene-3,4:9,10-tetra-carboxylic diimide] ([PDICC](2), 1) and 1,1'-ethynyl-bis[N,N'-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide] ([PDI](2)CC, 2). In these dimeric PDI molecules, NMR-based structural characterization became nontrivial because severe H-1 spectral broadening and greater than expected numbers of observed C-13 resonances substantially complicated the interpretation of traditional 1-D spectra. However, rational two-dimensional NMR approaches based on both homo- and heteronuclear couplings (H-1-H-1 COSY; H-1-C-13 HSQC), in conjunction with high-level structural DFT calculations (GIAO/B3LYP/6-31G(d,p)/PCM, chloroform), were readily applied to these structures, producing well-defined analytical characterization, and the associated methodology is described in detail. Furthermore, on the basis of dynamic NMR experiments, both 1 and 2 were found to exist in a perylene-centered conformational dynamic equilibrium (Delta G double dagger = 13-17 kcal/mol), which primarily caused the observed ambiguities in conventional 1-D spectra.