N,N-二丁基-5,6,12,13-四(4-叔丁基苯氧基)-3,4,9,10-苝二酰亚胺 | 335654-34-7

• 物质功能分类: 材料化学 - 发光材料
• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: N,N-二丁基-5,6,12,13-四(4-叔丁基苯氧基)-3,4,9,10-苝二酰亚胺
• 中文别名: 1,6,7,12-四(4-叔丁基苯氧基)-N,N'-二(2,6-二正丁基)苯基-3,4,9,10-苝四羧酸亚胺；红染料；红色荧光剂-b
• 英文名称: N,N'-dibutyl-1,6,7,12-tetra(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylic acid bisimide
• 英文别名: N,N'-dibutyl-1,6,7,12-tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic acid bisimide；N,N'-di(n-butyl)-1,6,7,12-tetra(4-tert-butylphenoxy)-3,4,9,10-perylenetetracarboxylic diimide；N,N'-dibutyl-1,6,7,12-tetra(4-tert-butylphenoxy)perylene-3,4:9,10-tetracarboxylic diimide；N,N'-dihexyl-1,6,7,12-tetra(4-tert-butylphenoxy)-perylene-3,4,9,10-tetracarboxylicdiimide；1,6,7,12-tetra(4'-t-butylphenoxy)-N,N'-di(n-butyl)-3,4,9,10-perylene tetracarboxylic diimide；N,N-dibutyl-5,6,12,13-tetrakis(4-(1,1-dimethylethyl)phenoxy)-3,4,9,10-perylenedicarboximide；7,18-dibutyl-11,14,22,26-tetrakis(4-tert-butylphenoxy)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone
• CAS: 335654-34-7
• 化学式: C₇₂H₇₄N₂O₈
• 分子量: 1095.39
• InChiKey: OBCUCPAGCITLSE-UHFFFAOYSA-N

物化性质

• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  19
• 重原子数：
  82
• 可旋转键数：
  18
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N-二丁基-5,6,12,13-四(4-叔丁基苯氧基)-3,4,9,10-苝二酰亚胺 在 氢氧化钾 、 盐酸 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以91.2%的产率得到1,6,7,12-四叔丁基苯氧基苝-3,4,9,10-四甲酸二酐
  参考文献：
  名称：

  四香豆素per体系中的分子内能量转移：溶剂和桥联单元对电子性能的影响。

  摘要：

  报道了一种新型香豆素供体-per联亚酰亚胺受体光收集系统的合成和表征，其中能量转移效率> 99％。将供体-受体体系与模型化合物的激发态性质进行比较表明，尽管the亚双酰亚胺受体单元的光物理性质受到酰亚胺位置上取代基的性质和所用溶剂的影响很大，但通过键间相互作用供体和受体单元之间的距离可以忽略不计。可以将本系统中的能量转移描述为经由空间能量转移机制发生。仔细考虑供体相对于受体单元的氧化还原性质可以避免潜在有害的激发态电子转移过程。

  DOI：

  10.1039/b711681k
• 作为产物：
  描述：

  1,6,7,12-四氯-3,4,9,10-苝四甲酸二酐 在 N-甲基吡咯烷酮 、 potassium carbonate 、 丙酸 作用下， 反应 16.0h， 生成 N,N-二丁基-5,6,12,13-四(4-叔丁基苯氧基)-3,4,9,10-苝二酰亚胺
  参考文献：
  名称：

  Synthesis of Diazadibenzoperylenes and Characterization of Their Structural, Optical, Redox, and Coordination Properties

  摘要：

  Tetraphenoxy-substituted diazadibenzoperylenes 5a,b were synthesized from tetrachloroperylene tetracarboxylic acid bisanhydride I through imidization with benzylamine, nucleophilic displacement of the four chlorine atoms by phenolates, carbonyl group reduction by LiAlH4/AlCl3, and subsequent Pd/C-promoted debenzylation-dehydrogenation. The structural properties of these extended diazaarenes are discussed on the basis of a X-ray crystal structure of the N,N'-dibutylated diazadibenzoperylenium dication 6, which revealed a 25degrees twist of the central six-membered ring leading to an atropisomeric pi-conjugated backbone. The chromophoric systems of 5 and 6 were characterized by optical absorption and fluorescence spectroscopy, which revealed an intense fluorescence with a quantum yield of 75% for 5 and 50% for 6. Cyclic voltammetry showed reversible oxidation and reduction waves for 6, whereas the oxidation of 5 afforded the irreversible deposition of a conductive film on the electrode surface. Finally, the potential use of ligands 5 in supramolecular chemistry has been evaluated by complexation experiments with carboxylic acids and zinc tetraphenylporphyrin (ZnTPP).

  DOI：

  10.1021/jo011133l

文献信息

• Fluorescent and Electroactive Cyclic Assemblies from Perylene Tetracarboxylic Acid Bisimide Ligands and Metal Phosphane Triflates
  作者：Frank Würthner、Armin Sautter、Dietmar Schmid、Peter J. A. Weber

  DOI：10.1002/1521-3765(20010216)7:4<894::aid-chem894>3.0.co;2-n

  日期：2001.2.16

  absorption and fluorescence properties and the electrochemistry and spectroelectrochemistry of both the perylene bisimide ligands and the perylene bisimide metal complexes show that Pt(II) coordination does not interfere with the optical and electrochemical properties of the perylene bisimide ligands; this gives squares with high fluorescence quantum yields (phiF (3a)=0.88) and three fully reversible redox

  合成了四芳氧基取代的苝四羧酸双酰亚胺，在酰亚胺官能团处具有一个或两个 4-吡啶基受体取代基，并用于与 Pd(II) 和 Pt(II) 膦三氟甲磺酸酯的过渡金属定向自组装。在混合组分后，观察到含有四种染料分子的功能性分子方形复合物和 2:1（苝双酰亚胺配体：过渡金属离子）化学计量的模型复合物的定量形成。分离出的金属超分子方块通过 1H 和 31P [1H] NMR 光谱以及传统的电喷雾电离 (ESI) 和 ESI-FTICR 质谱进行表征，这为这些巨型环状染料组件的结构和高稳定性（分子量）提供了证据(3a) 8172，Pt-Pt 角对角线约 3.4 nm）。苝双酰亚胺配体和苝双酰亚胺金属配合物的光吸收和荧光性质以及电化学和光谱电化学研究表明，Pt(II) 配位不会干扰苝双酰亚胺配体的光学和电化学性质；这给出了具有高荧光量子产率 (phiF (3a) = 0.88) 和三个完全可逆氧化还原对的
• Tuning energy transfer in switchable donor–acceptor systems
  作者：Johannes H. Hurenkamp、Jaap J. D. de Jong、Wesley R. Browne、Jan H. van Esch、Ben L. Feringa

  DOI：10.1039/b719095f

  日期：——

  The synthesis and characterisation of a coumarin–dithienylcyclopentene–coumarin symmetric triad (CSC) and a perylene bisimide–dithienylcyclopentene–coumarin asymmetric triad (PSC) are reported. In both triads the switching function of the photochromic dithienylcyclopentene unit is retained. For CSC an overall 50% quenching of the coumarin fluorescence is observed upon ring-closure of the dithienylcyclopentene component, which, taken together with the low PSS (<70%), indicates that energy transfer quenching of the coumarin component by the dithienylcyclopentene in the closed state is efficient. Upon ring opening of the dithienylcyclopentene unit the coumarin emission is restored fully. The PSC triad shows efficient energy transfer from the coumarin to the perylene bisimide unit when the dithienylcyclopentene unit is in the open state. When the dithienylcyclopentene is in the closed (PSS) state a 60% decrease in sensitized perylene bisimide emission intensity is observed due to competitive quenching of the coumarin excited state and partial quenching of the perylene excited state by the closed dithienylcyclopentene unit. This modulation of energy transfer is reversible over several cycles for both the symmetric and asymmetric tri-component systems.

  报道了香豆素-二噻吩基环戊烯-香豆素对称三联体（CSC）和苝双酰亚胺-二噻吩基环戊烯-香豆素不对称三联体（PSC）的合成和表征。在这两个三元组中，光致变色二噻吩基环戊烯单元的开关功能被保留。对于 CSC，在二噻吩基环戊烯组分闭环时观察到香豆素荧光总体 50% 猝灭，这与低 PSS (<70%) 一起表明香豆素组分通过二噻吩基环戊烯在关闭状态是有效的。当二噻吩基环戊烯单元开环时，香豆素发射完全恢复。当二噻吩基环戊烯单元处于开放状态时，PSC 三元组显示出从香豆素到苝双酰亚胺单元的有效能量转移。当二噻吩基环戊烯处于闭合 (PSS) 状态时，由于闭合二噻吩基环戊烯单元对香豆素激发态的竞争性猝灭和苝激发态的部分猝灭，观察到敏化苝双酰亚胺发射强度降低了 60%。对于对称和不对称三组分系统，这种能量转移的调制在几个周期内是可逆的。
• Highly soluble perylene tetracarboxylic diimides (PDI)-tetrathiafulvalene (TTF) dyad and TTF-PDI-TTF triad
  作者：Chengyun Wang、Wei Tang、Hanbin Zhong、Xuechao Zhang、Yongjia Shen

  DOI：10.1002/jhet.160

  日期：2009.9

  Two highly soluble donor-σ-acceptor and donor-σ-accepter-σ-donor type fluorescence switches consisting tetrathiafulvalene (TTF) and 3,4,9,10-perylene tetracarboxylic diimides (PDI) were synthesized. The structure of the dyad and triad as well as their intermediates was characterized by 1H NMR, 13C NMR MS, elemental analysis. Their fluorescence behavior could be modulated by oxidization and reduction

  两个高度可溶的供体-σ-受体和供体-σ-受体-σ-供体型荧光开关组成 合成了四硫富瓦烯（TTF）和3,4,9,10-per四羧酸二酰亚胺（PDI）。通过1 H NMR，13 C NMR MS，元素分析对二元组和三元组及其中间体的结构进行表征。可以使用化学或电化学方法通过TTF单元的氧化和还原来调节其荧光行为。J.杂环化​​学，（2009）。
• Novel soluble and thermally-stable fullerene dyad containing peryleneElectronic supplementary information (ESI) available: synthesis of starting materials and 1H-NMR, 13C-NMR, MS spectra and emission lifetimes of the products. See http://www.rsc.org/suppdata/jm/b3/b316996k/
  作者：Jianli Hua、Fanshun Meng、Fang Ding、Fuyou Li、He Tian

  DOI：10.1039/b316996k

  日期：——

  A novel fullerene dyad C606060–P1 in which a perylene moiety is attached to C60 through a pyrrolidine ring has been prepared by 1,3-dipolar cycloaddition of the azomethine ylides generated in situ from the corresponding aldehyde and sarcosine. Electrochemical and photophyscial studies of the dyad in solution have revealed that there is no significant ground-state electronic interaction between the covalently bonded perylene moiety and the fullerene. The photophysical investigations have also shown that there exists an effective photoinduced energy transfer from the perylene moiety to C60. A photovoltaic device made with the dyad has confirmed that photoinduced electron transfer does take place within the dyad; however, the efficiency of the electron transfer is negligible relative to the energy transfer.

  通过对相应的醛和肌氨酸原位生成的偶氮甲基酰化物进行 1,3-二极环加成，制备出了一种新型富勒烯二元化合物 C606060-P1，其中一个过烯分子通过一个吡咯烷环连接到 C60 上。对溶液中的二元化合物进行的电化学和光物理研究表明，共价键合的过烯分子与富勒烯之间不存在明显的基态电子相互作用。光物理研究还表明，从过烯分子到 C60 之间存在有效的光诱导能量转移。用这种二元化合物制造的光伏装置证实，在二元化合物内部确实存在光诱导电子转移；不过，相对于能量转移而言，电子转移的效率微乎其微。
• Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures
  作者：Frank Würthner、Christoph Thalacker、Armin Sautter、Wolfgang Schärtl、Wolfram Ibach、Olaf Hollricher

  DOI：10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w

  日期：2000.11.3

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.