N,N'-di(1-nonyldecyl)perylene-3,4,9,10-tetracarboxylic diimide | 130296-48-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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'-di(1-nonyldecyl)perylene-3,4,9,10-tetracarboxylic diimide
• 英文别名: N,N'-di(10-nonadecyl)perylene-3,4,9,10-bis(dicarboximide)；7,18-Di(nonadecan-10-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: 130296-48-9
• 化学式: C₆₂H₈₆N₂O₄
• 分子量: 923.376
• InChiKey: XGEHGGNNEJIZDI-UHFFFAOYSA-N

物化性质

• 熔点：
  97-99 °C
• 沸点：
  931.6±38.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  21.8
• 重原子数：
  68
• 可旋转键数：
  34
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-di(1-nonyldecyl)perylene-3,4,9,10-tetracarboxylic diimide 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
• 作为产物：
  描述：

  10-十九烷酮 在 吡啶 、 喹啉 、 盐酸羟胺 、 zinc diacetate 、 红铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 N,N'-di(1-nonyldecyl)perylene-3,4,9,10-tetracarboxylic diimide
  参考文献：
  名称：

  用于光伏应用的新型电子受体per二酰亚胺分子的合成与表征

  摘要：

  两个新的per二酰亚胺分子1、7-双（1-萘基）-N，N'-双-（10-十八烷基）-per-3,4,9,10-双（二甲叉酰亚胺）PDI-2和1，已合成7-双（5-ac烯基）-N，N'-双-（10-十八烷基）-per-3,4,9,10-双（二甲叉酰亚胺）PDI-3并用作P3HT / PDI体异质结太阳能电池。将稠合的芳环引入per核的海湾位置会产生强烈的空间位阻，扭曲the平面，直接影响相邻PDI之间的π-π分子内相互作用。所有这些特征有助于减少固态中的分子聚集，并对P3HT / PDI光伏器件的性能产生重大影响。

  DOI：

  10.1016/j.dyepig.2013.05.011

文献信息

• Side chain modification on PDI-spirobifluorene-based molecular acceptors and its impact on organic solar cell performances
  作者：Margherita Bolognesi、Desta Gedefaw、Marco Cavazzini、Marinella Catellani、Mats R. Andersson、Michele Muccini、Erika Kozma、Mirko Seri

  DOI：10.1039/c8nj04810j

  日期：——

  N-Substitution in perylene diimide (PDI) n-type semiconductors is critical for their performance in organic bulk heterojunction solar cells. In this work we synthesized and compared three perylene diimide-spirobifluorene derivatives, N-substituted with different alkyl side groups. These molecular systems were obtained by cost-effective methods, using straightforward synthetic procedures and easy purification

  per二酰亚胺（PDI）n型半导体中的N-取代对其在有机体异质结太阳能电池中的性能至关重要。在这项工作中，我们合成并比较了三种per二酰亚胺-螺二芴衍生物N-被不同的烷基侧基取代。这些分子系统是通过具有成本效益的方法，使用简单的合成程序和易于纯化而获得的。这些PDI衍生物用作电子受体材料，并与块状异质结太阳能电池中的基准喹喔啉-苯并二噻吩基供体聚合物混合。所有设备均通过在空气中进行刀片涂层以及使用非氯化溶剂进行处理。这三个分子表现出相同的HOMO / LUMO能级和非常相似的光学特性，但光伏响应不同。通过光学，电学和形态学特征讨论了这些不同的性能。基于在N位置具有支链和更长烷基的衍生物，有源层实现了最高的功率转换效率，
• Synthesis of donor–acceptor poly(perylene diimide-altoligothiophene) copolymers as n-type materials for polymeric solar cells
  作者：Erika Kozma、Dariusz Kotowski、Fabio Bertini、Silvia Luzzati、Marinella Catellani

  DOI：10.1016/j.polymer.2010.03.040

  日期：2010.5

  Donor–acceptor alternated copolymers based on perylene diimide units linked in bay positions with oligothiophene units were prepared and used as acceptor material in polymeric solar cells. The copolymers have exhibited ambipolar electrochemical properties, high electronic affinities and wide electronic absorption in the visible spectrum. The spectroscopical characterization of the copolymer blends with

  制备了基于per二酰亚胺单元在海湾位置与低聚噻吩单元连接的供体-受体交替共聚物，并将其用作聚合物太阳能电池中的受体材料。该共聚物在可见光谱中表现出双极性电化学性质，高电子亲和力和宽电子吸收率。具有聚-3-己基噻吩的共聚物共混物的光谱表征显示了表明电荷从the基共聚物转移到聚噻吩的证据。用共混物制备了全聚合物太阳能电池，这些器件的光伏特性显示转换效率分别为0.8％和0.4％。结果证明了per基共聚物作为有机太阳能电池中可加工的光敏受体的潜力。
• A joint experimental and theoretical study on the electro-optical properties of 1,6- and 1,7-fluorenyl disubstituted perylene diimide isomers
  作者：E. Kozma、W. Mróz、A. Andicsová Eckstein、V. Lukeš、F. Galeotti、A. Šišková、M. Danko、M. Catellani

  DOI：10.1039/c7nj03860g

  日期：——

  energy absorption at 570 nm and a strong band at 420 nm. The absorption and emission properties in different solvents have evidenced that although both regioisomers show dipole moment values of the excited states higher than those of the corresponding ground states, the dipole moment variation upon excitation is different for each isomer. Cyclic voltammetry measurements revealed that PDI-F2 has a stronger

  通过将各种官能团引入到len烯湾位置而获得的核取代的im二酰亚胺（PDI）是众所周知的用于光电应用的通用材料。the核的取代产生单，二和三取代的衍生物，这些衍生物受1,6-和1,7-二取代的PDI的区域异构体混合物支配。大多数情况下，由于难以通过常规方法或耗时的结晶过程分离它们，因此将二取代的异构体作为混合物使用。在这项工作中，由双[（9,9'-二辛基芴基）]- N的区域异构混合物，N'-双-（10-十八烷基）-per-3,4,9,10-双（二甲酰亚胺）， 1,6-（PDI-F1）和1,7-（PDI-F2异构体很容易通过柱色谱法分离和分离，随后进行表征。已经检查了PDI-F1的光谱特征，电子密度分布以及基态和激发态偶极矩，并将其与PDI-F2进行了比较。在两种PDI异构体的性质方面已观察到一些差异。该PDI-F1吸收光谱示出了独特的宽波段从450nm至640nm的跨越，而PDI-F2在570
• The synthesis of symmetric and asymmetric perylene derivatives and their optical properties
  作者：Sang Hyun Oh、Bong Gun Kim、Sun Ju Yun、Muchchintala Maheswara、Ketack Kim、Jung Yun Do

  DOI：10.1016/j.dyepig.2009.10.001

  日期：2010.4

  Symmetric bisimidazole and asymmetric imide-imidazole derivatives having a perylene structure were synthesized. Long, hyperbranched alkyl groups. attached to the benzimidazole moeity, enhanced the solubility of the imidazole derivatives. Soluble asymmetric imide-imidazoles were prepared using 1,2-diaminophenyls which contained methoxy. nitro and ester groups. The effects of both electron-withdrawing and donating groups were examined optically and electronically using both absorption and emission spectroscopy Photoluminescence spectroscopy revealed that the various perylene derivatives displayed varying quantum yield: frontier orbital energy levels were determined using cyclic voltammetric analysis. The asymmetric imide-imidazole displayed the transient. electronic and optical properties of symmetric bisimide and symmetric bisimidazole perylene derivatives Nitro derivation reduced the LUMO energy level of the asymmetric perylene by 0.05 eV while methoxy derivation increased it by 0.07 ev, in comparison with that of the unsubstituted, asymmetric perylene. Either bathochromic or hypsochromic spectral shifts of the asymmetric imidazoles were observed in solid film. depending oil electronic substituent. (C) 2009 Elsevier Ltd All rights reserved
• Effect of Side-Chain Substituents on Self-Assembly of Perylene Diimide Molecules:  Morphology Control
  作者：Kaushik Balakrishnan、Aniket Datar、Tammene Naddo、Jialing Huang、Randy Oitker、Max Yen、Jincai Zhao、Ling Zang

  DOI：10.1021/ja061810z

  日期：2006.6.1

  Effect of side-chain substitutions on the morphology of self-assembly of perylene diimide molecules has been studied with two derivatives modified with distinctly different side-chains, N, N'-di( dodecyl)-perylene-3,4,9,10-tetracarboxylic diimide ( DD-PTCDI) and N, N'-di( nonyldecyl)-perylene-3,4,9,10-tetracarboxylic diimide ( ND-PTCDI). Due to the different side-chain interference, the self-assembly of the two molecules results in totally different morphologies in aggregate: one-dimensional ( 1D) nanobelt vs zero-dimensional ( 0D) nanoparticle. The size, shape, and topography of the self-assemblies were extensively characterized by a variety of microscopies including SEM, TEM, AFM, and fluorescence microscopy. The distinct morphologies of self-assembly have been obtained from both the solution-based processing and surface-supported solvent-vapor annealing. The nanobelts of DD-PTCDI fabricated in solution can feasibly be transferred to both polar ( e. g., glass) and nonpolar ( e. g., carbon) surfaces, implying the high stability of the molecular assembly ( due to the strong pi-pi stacking). The side-chain-dependent molecular interaction was comparatively investigated using various spectrometries including UV-vis absorption, fluorescence, X-ray diffraction, and differential scanning calorimetry. Compared to the emission of ND-PTCDI aggregate, the emission of DD-PTCDI aggregate was significantly red-shifted ( ca. 30 nm) and the emission quantum yield decreased about three times, primarily due to the more favorable molecular stacking for DD-PTCID. Moreover, the aggregate of DD-PTCDI shows a pronounced absorption band at the longer wavelength, whereas the absorption of ND-PTCDI aggregate is not significant in the same wavelength region. These optical spectral observations are reminiscent of the previous theoretical investigation on the side-chain-modulated electronic properties of PTCDI assembly.