trans-4-(N,N-diphenylamino)stilbene | 406729-10-0

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: trans-4-(N,N-diphenylamino)stilbene
• 英文别名: 4-Styryltriphenylamine；N,N-diphenyl-4-[(E)-2-phenylethenyl]aniline
• CAS: 406729-10-0
• 化学式: C₂₆H₂₁N
• 分子量: 347.459
• InChiKey: DXYYLUGHPCHMRQ-WUKNDPDISA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  510.3±30.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  4-二苯胺基苯甲醛	4-(diphenylamino)benzaldehyde	4181-05-9	C19H15NO	273.334
  三苯胺	N,N-diphenylaminobenzene	603-34-9	C18H15N	245.324

反应信息

• 作为反应物：
  描述：

  trans-4-(N,N-diphenylamino)stilbene 以 正己烷 为溶剂， 生成 cis-4-(N,N-diphenylamino)stilbene
  参考文献：
  名称：

  邻氨基共轭对反式氨基苯乙烯的光化学的影响

  摘要：

  一系列反-2-（N-芳基氨基）对苯甲酸酯（芳基=苯基（o1H），4-甲基苯基（o1Me），4-甲氧基苯基（o1OM）和4-氰基苯基（o1CN）的激发态行为和报告了在非极性和极性溶剂中的反式-2-（N，N-二苯氨基）lb（o2）并与母体反式-2-氨基sti和相应的间位和对位异构体（m1R和p1R）进行了比较R = H，Me，OM和CN，以及m2和p2）。两种类型的扭转运动，即导致无荧光扭曲的分子内电荷转移（TICT）状态的D-A扭转和导致顺式异构体的C═C扭转，说明了o1R和o2的无辐射衰减。这些扭转的相对效率可以从他们的量子产率可以容易地评估荧光（Φ ˚F）和反式→顺式异构化（Φ TC）。所述d-A扭转的倾向是邻位和间位异构体，它类似于10M的> 1Me和忽略不计1H，1CN，和2。由温度依赖性荧光寿命确定的激活参数表明，C═C扭转主要通过邻位系统的三重态发生，其行为再次类似于间位异构体。

  DOI：

  10.1021/jp200774g
• 作为产物：
  描述：

  4-溴苄基亚磷酸二乙酯 在 tris(dibenzylideneacetone)dipalladium (0) 三叔丁基膦 、 sodium hydride 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.83h， 生成 trans-4-(N,N-diphenylamino)stilbene
  参考文献：
  名称：

  Fluorescence Enhancement of trans-4-Aminostilbene by N-Phenyl Substitutions:  The “Amino Conjugation Effect”

  摘要：

  The synthesis, structure, and photochemical behavior of the trans isomers of 4-(N-phenylamino)stilbene (1c), 4-(A methyl-N-phenylamino)stilbene (1d), 4-(NN-diphenylamino)stilbene (le), and 4-(N-(2,6dimethylphenyl)amino)stilbene (1f) are reported and compared to that of 4-aminostilbene (1a) and 4-N,N-dimethylaminostilbene (1b). Results for the corresponding 3-styrylpyridine (2) and 2-styrylnaphthalene analogues (3) are also included. The introduction of N-phenyl substituents to 4-aminostilbenes leads to a more planar ground-state geometry about the nitrogen atom, a red shift of the absorption and fluorescence spectra, and a less distorted structure with a larger charge-transfer character for the fluorescent excited state. Consequently, the N-phenyl derivatives 1c-e have low photoisomerization quantum yields and high fluorescence quantum yields at room temperature, in contrast to the behavior of la, 1b, and most unconstrained monosubstituted trans-stilbenes. The isomerization of 1c and 1d is a singlet-state process, whereas it is a triplet-state process for le, presumably due to a relatively higher singlet-state torsional barrier. The excited-state behavior of 1f resembles 1a and 1b instead of 1c-e as a consequence of the less planar amine geometry and weaker orbital interactions between the N-phenyl and the aminostilbene groups. Such an N-phenyl substituent effect is also found for 2 and 3 and thus appears to be general for stilbenoid systems. The nature of this effect can be described as an ''amino conjugation effect''.

  DOI：

  10.1021/ja016416+

文献信息

• Degenerate nonlinear absorption and optical power limiting properties of asymmetrically substituted stilbenoid chromophoresElectronic supplementary information (ESI) available: Experimental details. See http://www.rsc.org/suppdata/jm/b3/b313185h/
  作者：Tzu-Chau Lin、Guang S. He、Paras N. Prasad、Loon-Seng Tan

  DOI：10.1039/b313185h

  日期：——

  Two-photon absorption (2PA) spectra (650–1000 nm) of a series of model chromophores were measured via a newly developed nonlinear absorption spectral technique based on a single and powerful femtosecond white-light continuum beam. The experimental results suggested that when either an electron-donor or an electron-acceptor was attached to a trans-stilbene at a para-position, an enhancement in molecular two-photon absorptivity was observed in both cases, particularly in the 650–800 nm region. However, the push–pull chromophores with both the donor and acceptor groups showed larger overall two-photon absorption cross-sections within the studied spectral region as compared to their mono-substituted analogues. The combined results of the solvent effect and the 1H-NMR studies indicated that stronger acceptors produce a more efficient intramolecular charge transfer character upon excitation, leading to increased molecular two-photon responses in this model-compound set. A fairly good 2PA based optical power limiting behavior from one of the model chromophores is also demonstrated.

  通过一种基于单个强飞秒白光连续波束的新型非线性吸收光谱技术，测定了系列模型染料在650-1000 nm范围内的双光子吸收（2PA）光谱。实验结果表明，当电子供体或电子受体分别连接到反式-均二苯代乙烯的邻位时，两种情况下都观察到分子双光子吸收性的增强，尤其是在650-800 nm区域。然而，与单取代的类似物相比，同时含有供体和受体基团的推-拉型染料在整个研究光谱范围内表现出更大的双光子吸收截面。溶剂效应和1H-NMR研究的联合结果表明，更强的受体在激发时产生更有效的分子内电荷转移特性，导致该模型化合物系列中的分子双光子响应增强。其中一种模型染料的相当好的2PA基光学功率限制行为也被展示。
• Ketopyrroles useful as ligands in organic iridium compositions
  申请人：Chichak Kelly Scott

  公开号：US20080027028A1

  公开（公告）日：2008-01-31

  The present invention provides novel ketopyrroles having structure XXIV wherein R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cyclcoaliphatic radical; “a” is an integer from 0 to 3; and X 1 and X 2 are independently at each occurrence a bromine atom, a hydroxy group, or the group OR 10 , and wherein the group R 10 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cyclcoaliphatic radical. Ketopyrroles XXIV are useful ligands for the preparation of Type (1) and Type (2) organic iridium compositions. In one aspect, the present invention provides deuterated analogs of XXIV. Organic iridium compositions are useful in the preparation optoelectronic devices, such as OLED devices and photovoltaic devices exhibiting enhanced performance characteristics.

  本发明提供了具有结构XXIV的新型酮吡咯，其中R2在每次出现时独立地是氘原子、卤素、硝基、氨基、C3-C40芳香基、C1-C50脂肪基或C3-C40环脂基；“a”是从0到3的整数；X1和X2在每次出现时独立地是溴原子、羟基或基团OR10，其中基团R10在每次出现时独立地是氘原子、卤素、硝基、氨基、C3-C40芳香基、C1-C50脂肪基或C3-C40环脂基。酮吡咯XXIV是用于制备类型（1）和类型（2）有机铱配合物的有用配体。在一个方面，本发明提供了XXIV的氘代物。有机铱配合物在制备光电子器件方面很有用，例如OLED器件和光伏器件，表现出增强的性能特征。
• COMPOUND COMPRISING PHENYL PYRIDINE UNITS
  申请人：Ye Qing

  公开号：US20090289547A1

  公开（公告）日：2009-11-26

  Organic compounds of formula I may be used in optoelectronic devices wherein R 1 is, independently at each occurrence, a C 1 -C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical; R2 is, independently at each occurrence, a C 1 -C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical; a is, independently at each occurrence, an integer ranging from 0-4; b is, independently at each occurrence, an integer ranging from 0-3; Ar 1 is a direct bond or heteroaryl, aryl, or alkyl or cycloalkyl; Ar 2 is heteroaryl, aryl, or alkyl or cycloalkyl; c is 0, 1 or 2; and n is an integer ranging from 2-4.

  化学式I的有机化合物可用于光电子器件，其中R1在每次出现时独立地是C1-C20脂肪基、C3-C20芳香基或C3-C20环脂肪基；R2在每次出现时独立地是C1-C20脂肪基、C3-C20芳香基或C3-C20环脂肪基；a在每次出现时独立地是0-4之间的整数；b在每次出现时独立地是0-3之间的整数；Ar1是直接键或杂环芳基、芳基、烷基或环烷基；Ar2是杂环芳基、芳基、烷基或环烷基；c为0、1或2；n是2-4之间的整数。
• [EN] POLYMERS FOR USE IN ELECTRONIC DEVICES<br/>[FR] POLYMÈRES DESTINÉS À ÊTRE UTILISÉS DANS DES DISPOSITIFS ÉLECTRONIQUES
  申请人：DUPONT ELECTRONICS INC

  公开号：WO2020018617A1

  公开（公告）日：2020-01-23

  In Formula I: Qa is CRX, SiRx, GeRx, PRX, or N; Qb is CRy, SiRy, GeRy, PRy, or N; R1, R2, and R3 are the same or different at each occurrence and are F, CN, alkyl, fluoroalkyl, unsubstituted or substituted hydrocarbon aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, or siloxy, where adjacent R1 groups can be joined together to form a fused aromatic ring; Rx is H, F, CN, alkyl, fluoroalkyl, unsubstituted or substituted hydrocarbon aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, siloxy, or R6; Ry is H, F, CN, alkyl, fluoroalkyl, unsubstituted or substituted hydrocarbon aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, siloxy, or R7; R6 and R7 are the same or different and are NH2 ArNH2, or OArNH2; Ar is the same or different at each occurrence and is an unsubstituted or substituted C6-18 hydrocarbon aryl; m and n are the same or different and are an integer from 0-2, such that m + n < 2; x is an integer from 0-4; y and z are the same or different and are an integer from 0 to the maximum available.

  在公式I中：Qa是CRX，SiRx，GeRx，PRX或N；Qb是CRy，SiRy，GeRy，PRy或N；R1、R2和R3在每次出现时相同或不同，并且是F，CN，烷基，氟烷基，未取代或取代的碳氢基芳基，未取代或取代的杂环芳基，烷氧基，氟烷氧基，未取代或取代的芳氧基，硅烷基或硅氧基，其中相邻的R1基团可以结合在一起形成融合的芳香环；Rx是H，F，CN，烷基，氟烷基，未取代或取代的碳氢基芳基，未取代或取代的杂环芳基，烷氧基，氟烷氧基，未取代或取代的芳氧基，硅烷基，硅氧基或R6；Ry是H，F，CN，烷基，氟烷基，未取代或取代的碳氢基芳基，未取代或取代的杂环芳基，烷氧基，氟烷氧基，未取代或取代的芳氧基，硅烷基，硅氧基或R7；R6和R7相同或不同，并且是NH2 ArNH2或OArNH2；Ar在每次出现时相同或不同，并且是未取代或取代的C6-18碳氢基芳基；m和n相同或不同，并且是0-2的整数，使得m + n < 2；x是0-4的整数；y和z相同或不同，并且是0到最大可用的整数。
• SOLVENT-FREE CROSS-COUPLING REACTION, AND PRODUCTION METHOD USING SAID REACTION
  申请人：NATIONAL UNIVERSITY CORPORATION HOKKAIDO UNIVERSITY

  公开号：US20210387994A1

  公开（公告）日：2021-12-16

  Disclosed is a cross-coupling reaction method which forms a chemical bond selected from C—N, C—B, C—C, C—O and C—S bonds, the method comprising: preparing an aromatic compound (1) having a leaving group; preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic amino compound (2-1), a diboronic acid ester or the like (2-2), an aromatic boronic acid or the like (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; and performing a cross-coupling reaction of the compound (1) with the compound (2) in the presence of a palladium catalyst, a base and a compound (4) having a carbon-carbon double bond or a carbon-carbon triple bond, in the absence of a solvent.

  揭示了一种交叉偶联反应方法，形成所选的C—N、C—B、C—C、C—O和C—S键中的化学键，该方法包括：准备具有离去基团的芳香化合物（1）；准备能够发生交叉偶联反应的化合物（2），所选自芳香胺化合物（2-1）、二硼酸酯或类似物（2-2）、芳香硼酸或类似物（2-3）、具有羟基的芳香化合物（2-4）和具有硫醇基的芳香化合物（2-5）；在钯催化剂、碱和具有碳-碳双键或碳-碳三键的化合物（4）的存在下，在无溶剂的情况下，对化合物（1）与化合物（2）进行交叉偶联反应。