N-(10-nonadecyl)-3,4,9,10-perylenetetracarboxylic acid 3,4-anhydride-9,10-imide | 130296-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: N-(10-nonadecyl)-3,4,9,10-perylenetetracarboxylic acid 3,4-anhydride-9,10-imide
• 英文别名: 9-(1-nonyldecyl)-1H-isochromeno[6',5',4':10,5,6]anthra[2,1,9-def]isoquinoline-1,3,8,10(9H)-tetraone；18-Nonadecan-10-yl-7-oxa-18-azaheptacyclo[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: 130296-39-8
• 化学式: C₄₃H₄₇NO₅
• 分子量: 657.85
• InChiKey: UYALSJLLBYPRNO-UHFFFAOYSA-N

物化性质

• 熔点：
  308 °C
• 沸点：
  805.9±38.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(10-nonadecyl)-3,4,9,10-perylenetetracarboxylic acid 3,4-anhydride-9,10-imide 在 3-甲基吡啶 、 硫酸 、 溴 、 碘 、 铜 、 potassium hydroxide 作用下， 以 叔丁醇 为溶剂， 生成 9-bromoperylene-3,4-dicarboxylic anhydride
  参考文献：
  名称：

  Controlling UV/vis Absorption and Stokes Shifts in Highly Fluorescent Chromophores by Molecular Dynamics in Targeted Construction of Dyads

  摘要：

  Perylenedicarboximides were interlinked in their free pen-position to form dyads where the UV/vis absorptivity was amplified by exciton effects and the strong fluorescence bathochromically shifted by molecular dynamics. Applications of this type of dye with such increased Stokes shifts were discussed.

  DOI：

  10.1021/jo301417p
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 氢氧化钾 、 氢气 作用下， 生成 N-(10-nonadecyl)-3,4,9,10-perylenetetracarboxylic acid 3,4-anhydride-9,10-imide
  参考文献：
  名称：

  苝双酰亚胺单羧酸的合成

  摘要：

  描述了具有一个羧酸锚定基团的苝-双酰亚胺4的合成和性质。4 的性质受到羧酸基团和酰亚胺部分之间的间隔基的强烈影响。已经制备了具有脂肪族 (4d-4g) 和芳香族 (4a-4c) 间隔基的染料。

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<847::aid-ejoc847>3.0.co;2-3

文献信息

• The Synthesis of Perylenebisimide Monocarboxylic Acids
  作者：Heinz Langhals、Wolfgang Lona

  DOI：10.1002/(sici)1099-0690(199805)1998:5<847::aid-ejoc847>3.0.co;2-3

  日期：1998.5

  The synthesis and properties of perylene-bisimides 4 with one carboxylic acid anchor group are described. The properties of 4 are strongly influenced by the spacer between the carboxylic acid group and the imide moeity. Dyes with aliphatic (4d−4g) and aromatic (4a−4c) spacers have been prepared.

  描述了具有一个羧酸锚定基团的苝-双酰亚胺4的合成和性质。4 的性质受到羧酸基团和酰亚胺部分之间的间隔基的强烈影响。已经制备了具有脂肪族 (4d-4g) 和芳香族 (4a-4c) 间隔基的染料。
• Highly Efficient Light-Harvesting Organofullerenes
  作者：Rafael Gómez、José L. Segura、Nazario Martín

  DOI：10.1021/ol047451z

  日期：2005.2.1

  Diphenylmethanofullerene-perylenebisimide dyads and triads have been prepared as light harvesters and electron acceptors for the preparation of efficient organic solar cells. The presence of swallowtail chains on the perylene unit provides enhanced solubility and allows its complete characterization. [Structure: see text]

  已经制备了二苯基甲基富勒烯-per二酰亚胺二重体和三重体作为光收集器和电子受体，用于制备有效的有机太阳能电池。the单元上燕尾链的存在可提高溶解度，并使其具有完整的特征。[结构：看文字]
• Three-dimensional electron-accepting compounds containing perylene bis(dicarboximide)s as n-type organic photovoltaic materials
  作者：Yutaka Ie、Takahiro Sakurai、Seihou Jinnai、Makoto Karakawa、Kouichi Okuda、Shogo Mori、Yoshio Aso

  DOI：10.1039/c3cc43925a

  日期：——

  The synthesis of three-dimensional compounds containing perylene bis(dicarboximide) for application as acceptor materials in organic photovoltaics is reported. Physicochemical measurements as well as device evaluations revealed that the characteristic properties of these materials are derived from their three-dimensional structure.

  本研究报告介绍了含双二甲酰亚胺（Perylene bis(dicarboximide) ）的三维化合物的合成过程，这些化合物可用作有机光伏技术中的受体材料。物理化学测量和设备评估结果表明，这些材料的特性源于其三维结构。
• Dendritic oligothiophene bearing perylene bis(dicarboximide) groups as an active material for photovoltaic device
  作者：Yutaka Ie、Toshihiko Uto、Nobuhiro Yamamoto、Yoshio Aso

  DOI：10.1039/b819008a

  日期：——

  A dendritic oligothiophene containing perylene bis(dicarboximide) units was synthesized and its electronic properties and photovoltaic performance were investigated.

  合成了含有苝双（二酰亚胺）单元的树枝状寡噻吩，并对其电子特性和光电性能进行了研究。
• Effects of functional groups at perylene diimide derivatives on organic photovoltaic device application
  作者：Won Suk Shin、Hwan-Hee Jeong、Mi-Kyoung Kim、Sung-Ho Jin、Mi-Ra Kim、Jin-Kook Lee、Jae Wook Lee、Yeong-Soon Gal

  DOI：10.1039/b512983d

  日期：——

  Four soluble perylene diimide derivatives (PDIs) have been prepared and their UV–visible and photoluminescence (PL) spectroscopy, cyclic voltammetry (CV) and thermal properties were studied. ITO/PEDOT∶PSS/poly(3-hexylthiophene) (P3HT)∶PDIs/LiF/Al photovoltaic devices were fabricated with PDIs as electron accepting and transporting materials. The highest incident photon-to-current conversion efficiency (IPCE) of 19% at 495 nm and the power conversion efficiency (PCE) of 0.18% under AM 1.5 (100 mW cm−2) with a short-circuit current density (JSC) of 1.32 mA cm−2, an open circuit voltage (VOC) of 0.36 V, and a fill factor (FF) of 0.38 have been achieved with 1 ∶ 4 ratio of P3HT ∶ N,N′-di(1-nonadecyl)perylene-3,4,9,10-bis(dicarboximide) (PDI-C9) after annealing at 80 °C for 1 h. 1,7-Bis(N-pyrrolidinyl)-N,N′-dicyclohexyl-3,4,9,10-perylenebis(dicarboximide) (5-PDI), which has the electron donating pyrrolidinyl group, absorbed the long wavelength region to give IPCE onset higher than 750 nm and the pyrrolidinyl group also raised the LUMO level of 5-PDI to render the high VOC (up to 0.71 V) in photovoltaic device.

  制备了四种可溶性过二亚胺衍生物 (PDI)，并研究了它们的紫外可见光和光致发光 (PL) 光谱、循环伏安 (CV) 和热性能。以 PDIs 为电子接受和传输材料，制备了 ITO/PEDOT∶PSS/poly(3-hexylthiophene) (P3HT)∶PDIs/LiF/Al 光伏器件。在 AM 1.5（100 mW cm-2）、短路电流密度（JSC）为 1.在 80 °C 下退火 1 小时后，1 ∶ 4 比率的 P3HT ∶ N,N′-二（1-壬癸基）过烯-3,4,9,10-双（二甲酰亚胺）（PDI-C9）实现了 0.32 mA cm-2、0.36 V 的开路电压（VOC）和 0.38 的填充因子（FF）。1,7-双（N-吡咯烷基）-N,N′-二环己基-3,4,9,10-过烯双(二甲酰亚胺)（5-PDI）具有电子捐赠的吡咯烷基团，可吸收长波长区域，使 IPCE 的起始波长高于 750 nm，吡咯烷基团还提高了 5-PDI 的 LUMO 水平，使光伏器件具有高 VOC（高达 0.71 V）。