N,N’-bis(1-ethylpropyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene-3,4:9,10-tetracarboxylic acid bisimide | 1294450-29-5

• 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: N,N’-bis(1-ethylpropyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene-3,4:9,10-tetracarboxylic acid bisimide
• 英文别名: N,N'-bis(1-ethylpropyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene-3,4:9,10-tetracarboxylic acid bisimide；7,18-Di(pentan-3-yl)-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-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；7,18-di(pentan-3-yl)-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-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: 1294450-29-5
• 化学式: C₄₀H₄₁BN₂O₆
• 分子量: 656.586
• InChiKey: RPTRKVLYPGWUAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  49
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N’-bis(1-ethylpropyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene-3,4:9,10-tetracarboxylic acid bisimide 在 2-双环己基膦-2',6'-二甲氧基联苯 、 盐酸 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 水 、 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 41.0h， 生成 N,N’-bis(1-ethylpropyl)-6-trifluoromethylbenzo[b]peryleno[2,3,4-def][1,8]naphthyridin-1(2H)-one-11,12-dicarboxylic acid imide
  参考文献：
  名称：

  Synthesis of Pyridine-Fused Perylene Imides with an Amidine Moiety for Hydrogen Bonding

  摘要：

  Pyridine-fused perylene tetracarboxylic acid bisimides (PBIs) were synthesized via Suzuki-Miyaura coupling and acid condensation. The fused PBIs with electron-donating substituents exhibited an intramolecular charge transfer Interaction. One of the N-alkyl substituents was selectively removed with BBr3 to create an amidine guest binding site. A hydrogen bonding Interaction with pentafluorobenzoic acid changed the absorption spectra and enhanced fluorescence.

  DOI：

  10.1021/ol401316q
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 、 3-氨基戊烷 在 咪唑 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 三(五氟苯基)膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 52.0h， 生成 N,N’-bis(1-ethylpropyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)perylene-3,4:9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  异源per二酰亚胺阵列：有机太阳能电池中潜在的非富勒烯受体

  摘要：

  苝二酰亚胺（一种新的家庭PDI）阵列，异源酮（二PDI和三PDI），设计并通过使用两种异源的Suzuki交叉偶联反应有效地合成PDI单体与不同位置的托架-和邻位的3'-取代，分别。该化合物具有独特的光物理和电化学性能，已成功应用于非富勒烯有机太阳能电池中，三-PDI的功率转换效率高达4.55％。

  DOI：

  10.1039/c7tc03171h

文献信息

• Iridium-Catalyzed Direct Tetraborylation of Perylene Bisimides
  作者：Takuro Teraoka、Satoru Hiroto、Hiroshi Shinokubo

  DOI：10.1021/ol2004534

  日期：2011.5.20

  Treatment of perylene bisimides (PBIs) with bis(pinacolato)diboron in the presence of an iridium catalyst provides tetraborylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The planar structure of the perylene core has been confirmed by X-ray diffraction analysis. Oxidation of tetraborylated PBI with hydroxylamine hydrochloride affords tetrahydroxy PBI in excellent yield

  在铱催化剂的存在下用双（频哪醇）二硼处理双酰亚胺（PBI），可在2,5,8,11-位提供四硼化的PBI，产率高，具有良好的区域选择性。X核的平面结构已经通过X射线衍射分析确认。用盐酸羟胺将四硼化的PBI氧化可得到极佳的收率的四羟基PBI，由于羰基和羟基之间的分子内氢键相互作用，四羟基PBI表现出明显的蓝移吸收光谱。
• A simple molecular structure of ortho-derived perylene diimide diploid for non-fullerene organic solar cells with efficiency over 8%
  作者：Helin Wang、Lingcheng Chen、Yi Xiao

  DOI：10.1039/c7ta06804b

  日期：——

  A simple molecular structure of ortho-derived perylene diimides (PDI) diploid has been developed for non-fullerene organic solar cells (OSCs) with a high power conversion efficiency (PCE) of 8.3%, indicating that such a concise molecular structure with a high PCE has great potential for the practical applications in OSCs.

  一种简单的分子结构的邻位苝二酰亚胺（PDI）二倍体已经被开发用于非富勒烯有机太阳能电池（OSC），其具有高达8.3%的高功率转换效率（PCE），这表明这种简洁的分子结构具有在OSC实际应用中的巨大潜力。
• Constructing a donor–acceptor linear-conjugation structure for heterologous perylene diimides to greatly improve the photovoltaic performance
  作者：Helin Wang、Lingcheng Chen、Yi Xiao

  DOI：10.1039/c8tc04929g

  日期：——

  By applying the concept of an acceptor–donor–acceptor (A–D–A) structure, we have designed a new linear-conjugation perylene diimide (PDI) derivative Th-4PDI that contains four PDI units connected at different reactive positions. Th-4PDI is constructed via a coupling reaction between two heterologous PDI dimers (2PDI) as the acceptor parts and a thiophene as the donor unit. Th-4PDI possesses a broadened

  通过应用受体-施主-受体（AD-A）结构的概念，我们设计了一种新的线性共轭per二酰亚胺（PDI）衍生物Th-4PDI，其中包含四个连接在不同反应位置的PDI单元。Th-4PDI是通过两个作为受体部分的异源PDI二聚体（2PDI）和作为供体单元的噻吩之间的偶联反应而构建的。Th-4PDI在400至700 nm的范围内具有较宽的吸收光谱，并且其最低的未占据分子轨道（LUMO）水平为-4.03 eV。更重要的是，基于Th-4PDI的有源层薄膜与原型2PDI相比，它们具有更高的电荷迁移率，更平衡的载流子传输和更有利的纳米形态，这是在有机太阳能电池（OSC）中实现高效率的重要因素。结果，基于PTB7-Th：Th-4PDI的设备显示出7.17％的高功率转换效率（PCE），是2PDI的3倍。结果表明，基于2PDI构建A–D–A型共轭结构是在OSC中实现高PCE的可行策略，而且，通过合理设计，异源PDI
• Heterologous perylene diimide arrays: potential non-fullerene acceptors in organic solar cells
  作者：Helin Wang、Lingcheng Chen、Yi Xiao

  DOI：10.1039/c7tc03171h

  日期：——

  family of perylene diimide (PDI) arrays, heterologous ones (di-PDI and tri-PDI), were designed and efficiently synthesized by Suzuki cross-coupling reactions using two heterologous PDI monomers with different positions of bay- and ortho-substitution, respectively. The compounds exhibit unique photophysical and electrochemical properties and were successfully applied in non-fullerene organic solar cells

  苝二酰亚胺（一种新的家庭PDI）阵列，异源酮（二PDI和三PDI），设计并通过使用两种异源的Suzuki交叉偶联反应有效地合成PDI单体与不同位置的托架-和邻位的3'-取代，分别。该化合物具有独特的光物理和电化学性能，已成功应用于非富勒烯有机太阳能电池中，三-PDI的功率转换效率高达4.55％。
• Synthesis of Pyridine-Fused Perylene Imides with an Amidine Moiety for Hydrogen Bonding
  作者：Satoru Ito、Satoru Hiroto、Hiroshi Shinokubo

  DOI：10.1021/ol401316q

  日期：2013.6.21

  Pyridine-fused perylene tetracarboxylic acid bisimides (PBIs) were synthesized via Suzuki-Miyaura coupling and acid condensation. The fused PBIs with electron-donating substituents exhibited an intramolecular charge transfer Interaction. One of the N-alkyl substituents was selectively removed with BBr3 to create an amidine guest binding site. A hydrogen bonding Interaction with pentafluorobenzoic acid changed the absorption spectra and enhanced fluorescence.