2-(4-hydroxy-3-methoxystyryl)-1-methylquinolinium 4-hydroxybenzenesulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-hydroxy-3-methoxystyryl)-1-methylquinolinium 4-hydroxybenzenesulfonate
• 英文别名: 4-Hydroxybenzenesulfonate;2-methoxy-4-[2-(1-methylquinolin-1-ium-2-yl)ethenyl]phenol；4-hydroxybenzenesulfonate;2-methoxy-4-[2-(1-methylquinolin-1-ium-2-yl)ethenyl]phenol
• 化学式: C₆H₅O₄S*C₁₉H₁₈NO₂
• 分子量: 465.527
• InChiKey: FOZYXDXQCXFWCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-[(E)-2-(4-hydroxy-3-methoxystyryl)-1-methyl]quinolinium iodide 、 sodium p-hydroxybenzenesulfonate 以 甲醇 为溶剂， 以45%的产率得到2-(4-hydroxy-3-methoxystyryl)-1-methylquinolinium 4-hydroxybenzenesulfonate
  参考文献：
  名称：

  Crystal Engineering of Acentric Styryl Quinolinium Crystals with Strongly Hydrogen-Bonded Phenolic Anions

  摘要：

  We report on new acentric styryl quinolinium crystals with phenolic sulfonate counteranions and investigate their supramolecular interactions that affect their quadratic non-linear optical properties. The phenolic group acting as an electron-donor as well as hydrogen-bond donor site is located at one end of the anion, while the sulfonate group acting as an electron-acceptor as well as hydrogen-bond acceptor site is located at the opposite end of the anion. New styryl quinolinium crystals with 4-hydroxybenzenesulfonate and 6-hydroxynaphthalene-2-sulfonate counteranions exhibit a large macroscopic optical nonlinearity with very efficient second harmonic generation (SHG) efficiency. In styryl quinolinium 4-hydroxybenzenesulfonate crystals, the styryl quinolinium cation chromophores exhibit an acentric ordering with a high order parameter close to 1.0, which is optimal for electro-optic applications or THz-wave generation. The 4-hydroxybenzenesulfonate counteranions form strong head-to-tail hydrogen bonds, and they are also packed in acentric layers. The direction of the polar axes in cation and anion layers is practically identical. Therefore, the introducing phenolic group acting as an electron-donor as well as hydrogen-bond donor to the sulfonate counteranion is a potential technique for crystal engineering to tailor molecular ordering as well as the physical properties of salt-type quinolinium derivatives.

  DOI：

  10.1021/cg401261z

文献信息

• QUINOLINIUM SINGLE CRYSTALS FOR USE IN NONLINEAR OPTICS
  申请人：AJOU UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION

  公开号：US20140204457A1

  公开（公告）日：2014-07-24

  The present invention relates to quinolinium-derived single crystals for use in nonlinear optics, which exhibit high molecular orientation and macroscopic optical nonlinearity. When the quinolinium-derived crystals according to the present invention are applied to THz wave light sources, higher THz wave generating efficiency may be obtained as compared with inorganic crystals or existing organic M crystals.

  本发明涉及用于非线性光学的喹啉衍生物单晶，其具有高分子取向和宏观光学非线性性。当根据本发明的喹啉衍生物晶体应用于THz波光源时，与无机晶体或现有有机M晶体相比，可以获得更高的THz波产生效率。
• US9057929B2
  申请人：——

  公开号：US9057929B2

  公开（公告）日：2015-06-16
• Crystal Engineering of Acentric Styryl Quinolinium Crystals with Strongly Hydrogen-Bonded Phenolic Anions
  作者：Ji-Soo Kim、Jae-Hyeok Jeong、Hoseop Yun、Mojca Jazbinsek、Jun Wan Kim、Fabian Rotermund、O-Pil Kwon

  DOI：10.1021/cg401261z

  日期：2013.11.6

  We report on new acentric styryl quinolinium crystals with phenolic sulfonate counteranions and investigate their supramolecular interactions that affect their quadratic non-linear optical properties. The phenolic group acting as an electron-donor as well as hydrogen-bond donor site is located at one end of the anion, while the sulfonate group acting as an electron-acceptor as well as hydrogen-bond acceptor site is located at the opposite end of the anion. New styryl quinolinium crystals with 4-hydroxybenzenesulfonate and 6-hydroxynaphthalene-2-sulfonate counteranions exhibit a large macroscopic optical nonlinearity with very efficient second harmonic generation (SHG) efficiency. In styryl quinolinium 4-hydroxybenzenesulfonate crystals, the styryl quinolinium cation chromophores exhibit an acentric ordering with a high order parameter close to 1.0, which is optimal for electro-optic applications or THz-wave generation. The 4-hydroxybenzenesulfonate counteranions form strong head-to-tail hydrogen bonds, and they are also packed in acentric layers. The direction of the polar axes in cation and anion layers is practically identical. Therefore, the introducing phenolic group acting as an electron-donor as well as hydrogen-bond donor to the sulfonate counteranion is a potential technique for crystal engineering to tailor molecular ordering as well as the physical properties of salt-type quinolinium derivatives.