3-methoxy-N-(3-methoxyphenyl)-N-phenylaniline

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-methoxy-N-(3-methoxyphenyl)-N-phenylaniline
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: UJAAHRLTTNJBPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-N-(3-methoxyphenyl)-N-phenylaniline 在 哌啶 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 11.0h， 生成 (2Z,2'Z)-diethyl 2,2'-(((1E,1'E)-((phenylazanediyl)bis(2-methoxy-4,1-phenylene))bis(ethene-2,1-diyl))bis(5,5-dimethylcyclohex-2-en-3-yl-1-ylidene))bis(2-cyanoacetate)
  参考文献：
  名称：

  Methoxy supported, deep red emitting mono, bis and tris triphenylamine-isophorone based styryl colorants: Synthesis, photophysical properties, ICT, TICT emission and viscosity sensitivity

  摘要：

  A novel strategy for the synthesis of triphenylamine based and methoxy supported deep red emitting push-pull chromophores is developed. The methoxy groups though not in conjugation with the acceptor exhibited a red shifted absorption and emissions (670 nm) as compared to the unsubstituted analogues due to the improved donating ability of triphenylamine. The dyes show high molar extinction coefficients (1, 65,800 M-1 cm(-1)) and as the number of withdrawing groups increases the molar extinction coefficient and emission intensity increase. Positive solvatochromism (96 nm) was observed which is well supported by linear and multi-linear regression. The mono styryl dyes showed enhancement of fluorescence while the di and tri-styryl dyes show quenching of fluorescence in polar solvents, which is correlated with the intramolecular charge transfer and twisted intramolecular charge transfer. Viscosity induced emission enhancement has also been observed. The experimental. findings were correlated theoretically by using Density Functional theory computations. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.08.025
• 作为产物：
  描述：

  苯胺 、 三氟甲烷磺酸3-甲氧基-2-(三甲基硅基)苯酯 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以94%的产率得到3-methoxy-N-(3-methoxyphenyl)-N-phenylaniline
  参考文献：
  名称：

  胺和磺酰胺的简便N-芳基化以及苯酚和亚芳基羧酸的O-芳基化

  摘要：

  通过使这些底物在存在下与多种邻甲硅烷基芳基三氟甲磺酸酯反应，已实现了一种有效的，无过渡金属的胺，磺酰胺和氨基甲酸酯的N-芳基化以及酚和羧酸的O-芳基化方法。的CsF。在非常温和的反应条件下，芳基化产物的收率好至极好。这种化学反应易于耐受各种官能团。

  DOI：

  10.1021/jo0602221

文献信息

• [EN] SMALL-MOLECULE ORGANIC DYES<br/>[FR] COLORANTS ORGANIQUES À PETITES MOLÉCULES
  申请人：UNIV BASEL

  公开号：WO2019057451A1

  公开（公告）日：2019-03-28

  The present invention relates to compounds of formula (A), wherein Z is NR10 or O. These compounds represent novel acridinium and xanthylium salts having an unprecedented substituted heterocyclic core. They are useful as fluorescent dyes or precursors thereof in different applications including various imaging and sensing techniques, and, in particular, as photosensitizers and hereby preferably as photocatalysts. The present invention further relates to processes for preparing the inventive compounds via 1,5-organodimetallic reagents from double directed ortho-metalation reactions or combined halogen-metal exchange/ directed ortho-metalation reactions.

  本发明涉及式(A)的化合物，其中Z为NR10或O。这些化合物代表具有前所未有的取代杂环核的新型吖啶和黄色素盐。它们可用作不同应用中的荧光染料或其前体，包括各种成像和传感技术，特别是作为光敏剂，最好作为光催化剂。本发明还涉及通过1,5-有机二金属试剂从双向导向的邻金属化反应或联合卤素金属交换/导向的邻金属化反应制备创新化合物的方法。
• Synthesis of 1,5-bifunctional organolithium reagents by a double directed ortho-metalation: Direct transformation of esters into 1,8-dimethoxy-acridinium salts
  作者：Christian Fischer、Christof Sparr

  DOI：10.1016/j.tet.2018.04.060

  日期：2018.9

  electrophilic aromatic substitution amounts to several limitations in accessing specific substitution patterns. Nucleophiles generated by directed metalation represent an effective alternative for the preparation of various distinctly substituted arenes and heterocyclic scaffolds to overcome these restraints. Herein, we report the direct synthesis of specifically substituted heterocyclic fluorophores from esters

  电子和位阻因素对亲电子芳族取代度选择性的影响达到了访问特定取代方式的几个限制。通过定向金属化生成的亲核试剂是制备各种明显取代的芳烃和杂环骨架以克服这些限制的有效替代方法。在此，我们从酯通过加入从双定向1,5-双官能的有机金属试剂报告特定取代的杂环荧光团的直接合成邻-metalation（DD ÒM）。双（3-甲氧基苯基）胺被有效地二锂化，并用于合成具有独特的光物理和电化学性质的1,8-二甲氧基-啶鎓盐。这些新染料的单个还原电势，水溶性和亮度，有望在催化，成像和材料科学中有不同的应用。
• Novel triphenylamine based rhodamine derivatives: synthesis, characterization, photophysical properties and viscosity sensitivity
  作者：Shantaram Kothavale、Nagaiyan Sekar

  DOI：10.1039/c6ra19899f

  日期：——

  triphenylamine substituted derivatives showed larger Stokes shift and emission in the NIR region. All these newly synthesized rhodamine derivatives show comparatively larger Stokes shift (44–135 nm) than the commercially available Rhodamine B and Rhodamine 101. In their open form they are found to exhibit different emission color from pink (619 nm) to dark blue (719 nm) in day as well as UV-light.

  合成了五种新的基于三苯胺的深红色至近红外发射的若丹明衍生物，并通过1 H和13 C NMR光谱学和元素分析对其进行了表征。所有这些衍生物的光物理性质都以其螺环形式和开放形式进行了研究。与普通罗丹明衍生物相比，发现羟基取代的衍生物显示出红移排放，而三苯胺取代的衍生物在近红外区显示出更大的斯托克斯位移和发射。所有这些新合成的若丹明衍生物都比市售的若丹明B和若丹明101表现出相对更大的斯托克斯位移（44–135 nm）。在开放状态下，它们在白天以及紫外光下会显示出从粉红色（619 nm）到深蓝色（719 nm）的不同发射颜色。我们还研究了染料RH-2的加成酸（甲苯中的TFA）从螺环到开环形式的相互转化。对它们的粘度敏感性进行了研究，发现它们在极性粘性介质（如乙醇-甘油）中以开放形式显示出非常高的荧光增强作用。
• Yellow-red emitting, methoxy substituted triphenylamine-based styryl derivatives: Synthesis, photophysical properties, viscosity sensitivity, aggregation induced emission, NLO properties, and DFT study
  作者：Sulochana Bhalekar、Shantaram Kothavale、Nagaiyan Sekar

  DOI：10.1016/j.jphotochem.2019.112027

  日期：2019.11

  designed and synthesized to study the effect of auxiliary methoxy substituent on aggregation induced emission (AIE) and viscosity sensitivity. Instead of elongated, short conjugated dicyanovinyl derivatives are preferred for the improved AIE and viscosity sensitivity properties. The sensitivity study of fluorescence emission towards viscosity and polarity of organic solvents was investigated by UV visible

  设计并合成了三种新型的基于三苯胺的荧光分子转子（FMR），以研究辅助甲氧基取代基对聚集诱导发射（AIE）和粘度敏感性的影响。为了改善AIE和粘度敏感性，优选使用长的，短的共轭二氰基乙烯基衍生物代替长的。通过紫外可见溶剂变色研究对荧光发射对有机溶剂的粘度和极性的敏感性进行了研究，而AIE研究则在DMF-水的混合溶剂中进行。所有化合物的特征在于1 H和1313 C NMR，质谱IR以及元素分析。它们在544–620 nm之间表现出非常好的固态发射。观察到它们的一阶和二阶超极化率较高（378-1755х10^ -36 esu）。“双光子吸收截面”在168-229 GM为范围3.有效电荷转移是使用马利肯静寂分析阐明。
• Photoelectric conversion element, dye-sensitized solar cell, metal complex dye, dye composition, and oxide semiconductor electrode
  申请人：FUJIFILM Corporation

  公开号：US11094474B2

  公开（公告）日：2021-08-17

  A photoelectric conversion element includes a conductive support, a photoconductor layer including an electrolyte, a charge transfer layer including an electrolyte, and a counter electrode, in which the photoconductor layer has semiconductor fine particles carrying a metal complex dye represented by a specific formula.

  一种光电转换元件包括导电支架、包括电解质的光电导体层、包括电解质的电荷转移层和对电极，其中光电导体层具有携带以特定公式表示的金属络合染料的半导体微粒。