(5-(4-(diphenylamino)phenyl)thiophen-2-yl)boronic acid | 1352915-40-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (5-(4-(diphenylamino)phenyl)thiophen-2-yl)boronic acid
• 英文别名: 4-(5-boronic acid thiophen-2-yl)triphenylamine
• CAS: 1352915-40-2
• 化学式: C₂₂H₁₈BNO₂S
• 分子量: 371.267
• InChiKey: QPAOXJYEYNCFFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  589.4±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.7
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5-(4-(diphenylamino)phenyl)thiophen-2-yl)boronic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 5.25h， 生成
  参考文献：
  名称：

  From Terminal to Spiro‐Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes

  摘要：

  摘要 磷基化合物作为一种前景广阔的光功能材料备受关注。作为对这一新兴领域的贡献，我们介绍了一系列供体-受体离子染料，它们是通过将膦（A）和扩展的 π-NR2 （D）片段定制到蒽框架上而构建的。在二氯甲烷中，改变带有末端 -+PPh2Me 基团的物种中的电子供体的 π-间隔物会显示出长吸收波长（λabs=527 nm），并将发射转移到近红外（NIR）区域（噻吩基苯胺供体的发射波长为 λ=805 nm），但量子产率较低（Φ<0.01）。反过来，P-杂环受体的引入大大缩小了光带隙，提高了荧光效率。特别是，磷螺分子可以实现近红外发射（二氯甲烷中 797 纳米），荧光效率高达 Φ=0.12。磷-螺成分的电子接受特性优于单环和端基鏻成分，为设计新型电荷转移发色团指明了方向。

  DOI：

  10.1002/chem.202301073
• 作为产物：
  描述：

  4-溴三苯胺 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.75h， 生成 (5-(4-(diphenylamino)phenyl)thiophen-2-yl)boronic acid
  参考文献：
  名称：

  强可见光吸收环金属化铱 (III) 配合物的开发，用于稳健高效的光驱动制氢

  摘要：

  强和宽带 UV-Vis 吸收在基于铱 (III) 的光敏剂中用于光催化制氢很重要。该研究揭示了在 C^N 配体上选择合适的电子供体以提高性能的重要性。使用基于三苯胺的 Ir(III) PSs 在提高光催化性能方面显示出巨大的潜力。

  DOI：

  10.1002/chem.202104575

文献信息

• 三苯胺偶联的氟硼吡咯衍生物及其制备方法
  申请人：江苏大学

  公开号：CN107573368B

  公开（公告）日：2020-07-31

  本发明涉及氟硼吡咯衍生物，特指一类新的二氟硼二吡咯甲川化合物及其制备方法和运用荧光染料，属于荧光探针方面的内容，具体在于将三苯胺基团与氟硼吡咯结合，获得四种新型氟硼吡咯衍生物，都是很好的荧光染料，尤其是BODIPY‑TTPA2和3，其激发和发射都是在600nm以上，这两个化合物都是近红光吸收和近红外荧光发射的化合物，可望应用于荧光探针作为细胞或生物体内成像，减少了背景干扰。
• Sequential Coupling Approach to the Synthesis of Nickel(II) Complexes with <i>N</i>-aryl-2-amino Phenolates
  作者：Shinichiro Fuse、Hiroaki Tago、Masato M. Maitani、Yuji Wada、Takashi Takahashi

  DOI：10.1021/co3000665

  日期：2012.10.8

  A sequential multicomponent coupling approach is a powerful method for the construction of combinatorial libraries because structurally complex and diverse molecules can be synthesized from simple materials in short steps. In this paper, an efficient synthesis of nickel(II) complexes with N-aryl-2-amino phenols via a sequential three-step coupling approach is described, for potential use in nonlinear optical materials, bioinspired catalytic systems, and near-infrared absorbing filters. Seventeen N-aryl-2-amino phenolates were successfully synthesized in high yields based on the coupling of 3,5-di-tertbutylbenzene-1,2-diol with a pivotal aromatic scaffold, 4-bromo-2-iodo-aniline, followed by sequential Suzuki-Miyaura coupling with aryl boronates. A total of 16 analytically pure nickel(II) complexes with N-aryl-2-amino phenolates were obtained from 17 complexation trials. The procedure allowed us to assemble 4 components in high yields without protection, deprotection, oxidation or reduction steps. Various building blocks that included electron-donating, electron-withdrawing, and basic were used, and readily available, nontoxic and environmentally benign substrates and reagents were employed with no generation of toxic compounds. No strict anhydrous or degassed conditions were required. Absorption spectroscopic measurement of the synthesized nickel(II) complexes revealed that the ortho-substituent Ar-1 exerted more influence on the absorption wavelength of the complexes than the para-substituent Ar-2. On the other hand, both substituents Ar-1 and Ar-2 influenced the molar absorptivity values. These observations should be useful for the design of new and useful nickel(II) complexes as near-infrared chromophores.
• Dipolar organic pyridyl dyes for dye-sensitized solar cell applications
  作者：Hsien-Hsin Chou、Chih-Yu Hsu、Ying-Chang Hsu、Yu-Sheng Lin、Jiann T. Lin、Chiitang Tsai

  DOI：10.1016/j.tet.2011.10.038

  日期：2012.1

  New dipolar dyes containing arylamine as the electron donor, 2-cyanoacrylic acid as the acceptor, and a conjugated spacer with incorporation of 2,5-pyridyl entity have been synthesized. Photophysical and electrochemical measurements, and theoretical computation were carried on these dyes. The solar cell devices using these dyes as the sensitizers exhibited light-to-electricity efficiencies in the range of 4.28-5.27%, which reaches 60-72% of N719-based device fabricated and measured under similar conditions. Better DSSC performance can be achieved with the dye where pyridine group is attached to thienyl or fluorenyl group because of favorable resonance energy and/or coplanarity for more effective charge transfer. (C) 2011 Elsevier Ltd. All rights reserved.