2-[[4-(Diethylamino)phenyl]methylideneamino]-5-nitrophenol | 389612-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[[4-(Diethylamino)phenyl]methylideneamino]-5-nitrophenol
• 英文别名: 2-[[4-(diethylamino)phenyl]methylideneamino]-5-nitrophenol
• CAS: 389612-91-3
• 化学式: C₁₇H₁₉N₃O₃
• 分子量: 313.356
• InChiKey: FOBSAPSFJXNMMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二苯基二烃基硼酸 、 2-[[4-(Diethylamino)phenyl]methylideneamino]-5-nitrophenol 反应 2.0h， 以74%的产率得到N,N-diethyl-4-((2,2-diphenyl-6-nitrobenzo[d][1,3,2]oxazaborol-3(2H)-ylidene)methyl) benzenamine
  参考文献：
  名称：

  Synthesis, X-ray diffraction analysis, and chemical–optical characterizations of boron complexes from bidentate ligands

  摘要：

  Herein is reported the synthesis and X-ray diffraction analysis for three boron complexes (2a-2c) prepared from the reaction of bidentate ligands (1a-1c) and diphenylborinic acid. Chemical characterization for the borinates is completed with IR. UV-Vis and NMR techniques, particularly B-11 NMR spectra confirmed the formation of boron complexes. X-ray diffraction analysis showed that for compounds 2a and 2c a non-planar conformation for the main pi-backbone is acquired after boron complexation; for compound 2b the planar conformation is preserved. Additionally, cubic nonlinear optical (NLO) properties were evaluated, through the optical susceptibility chi((3)) (-3 omega, omega, omega, omega), using the THG Maker-Fringes technique. Results showed that chi((3)) response decreases from ligands to boron complexes: this behavior could be attributed to a structural conformation or deformation of the electronic pi-system after boron complexation. The demonstrated electronic and structural features of these borinates could be useful for new strategies in the design of novel NLO dyes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.06.043
• 作为产物：
  描述：

  N,N-二乙基-4-氨基苯甲醛 、 2-氨基-5-硝基苯酚 以 甲醇 为溶剂， 反应 5.0h， 生成 2-[[4-(Diethylamino)phenyl]methylideneamino]-5-nitrophenol
  参考文献：
  名称：

  Synthesis and Spectrophotometric PH Sensing Applications of Poly-2-[4-(diethylaminophenyl)imino]-5-nitro-phenol and its Schiff Base Monomer for Two Different PH Ranges

  摘要：

  制备了聚-2-[4-(二乙基氨基苯基)亚氨基]-5-硝基酚（PEAPINP）和 2-[4-(二乙基氨基苯基)亚氨基]-5-硝基酚（EAPINP）作为新型 pH 传感器。研究了新型传感器在不同 pH 值下的分光光度和分光荧光响应。EAPINP 在 PH 值为 8 至 9 的碱性环境下具有线性响应能力，可用于吸收和波长辐射测量法。PEAPINP 在较低的 PH 值（6 至 7）下具有线性响应能力，可用作该范围内的另一种 pH 传感器。新传感器在酸性和中性介质中呈黄色，在碱性 PH 值中呈红色。EAPINP 和 PEAPINP 在不同 pH 值范围内的比色反应可用于开发颜色可调的 PH 传感器。

  DOI：

  10.1007/s10895-011-0983-3

文献信息

• Synthesis and Spectrophotometric PH Sensing Applications of Poly-2-[4-(diethylaminophenyl)imino]-5-nitro-phenol and its Schiff Base Monomer for Two Different PH Ranges
  作者：İsmet Kaya、Aysel Aydın、Mehmet Yıldırım

  DOI：10.1007/s10895-011-0983-3

  日期：2012.1

  Poly-2-[4-(diethylaminophenyl)imino]-5-nitro-phenol (PEAPINP) and 2-[4-(diethylaminophenyl)imino]-5-nitro-phenol (EAPINP) were prepared as new pH sensors. Spectrophotometric and spectrofluorometric response of the novel sensors in various pH values were investigated. EAPINP has the ability to respond linearly at alkaline PH values, 8 to 9, and can be utilized in absorption and wavelength radiometric methods. PEAPINP has the ability to respond linearly at lower pH values, 6 to 7, and can be used as an alternative pH sensor in this range. The new sensors are yellow-colored in acidic and neutral media and red-colored in alkaline PHs. With their colorimetric responses at different pH ranges EAPINP and PEAPINP can be used to develop color-tunable PH sensors.

  制备了聚-2-[4-(二乙基氨基苯基)亚氨基]-5-硝基酚（PEAPINP）和 2-[4-(二乙基氨基苯基)亚氨基]-5-硝基酚（EAPINP）作为新型 pH 传感器。研究了新型传感器在不同 pH 值下的分光光度和分光荧光响应。EAPINP 在 PH 值为 8 至 9 的碱性环境下具有线性响应能力，可用于吸收和波长辐射测量法。PEAPINP 在较低的 PH 值（6 至 7）下具有线性响应能力，可用作该范围内的另一种 pH 传感器。新传感器在酸性和中性介质中呈黄色，在碱性 PH 值中呈红色。EAPINP 和 PEAPINP 在不同 pH 值范围内的比色反应可用于开发颜色可调的 PH 传感器。
• Synthesis, X-ray diffraction analysis, and chemical–optical characterizations of boron complexes from bidentate ligands
  作者：Mario Rodríguez、José Luis Maldonado、Gabriel Ramos-Ortíz、Oscar Domínguez、Ma. Eugenia Ochoa、Rosa Santillan、Norberto Farfán、Marco-Antonio Meneses-Nava、Oracio Barbosa-García

  DOI：10.1016/j.poly.2012.06.043

  日期：2012.8

  Herein is reported the synthesis and X-ray diffraction analysis for three boron complexes (2a-2c) prepared from the reaction of bidentate ligands (1a-1c) and diphenylborinic acid. Chemical characterization for the borinates is completed with IR. UV-Vis and NMR techniques, particularly B-11 NMR spectra confirmed the formation of boron complexes. X-ray diffraction analysis showed that for compounds 2a and 2c a non-planar conformation for the main pi-backbone is acquired after boron complexation; for compound 2b the planar conformation is preserved. Additionally, cubic nonlinear optical (NLO) properties were evaluated, through the optical susceptibility chi((3)) (-3 omega, omega, omega, omega), using the THG Maker-Fringes technique. Results showed that chi((3)) response decreases from ligands to boron complexes: this behavior could be attributed to a structural conformation or deformation of the electronic pi-system after boron complexation. The demonstrated electronic and structural features of these borinates could be useful for new strategies in the design of novel NLO dyes. (C) 2012 Elsevier Ltd. All rights reserved.