有机化学 ›› 2014, Vol. 34 ›› Issue (2): 382-386.DOI: 10.6023/cjoc201307040 上一篇    下一篇

研究论文

吡啶并[2,3-d]嘧啶衍生物受体的合成及对阴离子识别研究

黄志斌, 刘学成, 胡明华, 林伟, 史达清   

  1. 苏州大学材料与化学化工学部 江苏省有机合成重点实验室 苏州 215123
  • 收稿日期:2013-07-25 修回日期:2013-10-12 发布日期:2013-10-16
  • 通讯作者: 史达清 E-mail:dqshi@suda.edu.cn
  • 基金资助:

    江苏省高校自然科学基金(No.11KJB150014)资助项目.

Synthesis of Receptors Based on Pyridio[2,3-d]pyrimidines and Their Anion Recognition

Huang Zhibin, Liu Xuecheng, Hu Minghua, Lin Wei, Shi Daqing   

  1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123
  • Received:2013-07-25 Revised:2013-10-12 Published:2013-10-16
  • Supported by:

    Project supported by the Natural Science Fundation of Jiangsu Higher Education Institutions (No. 11KJB150014).

通过6-氨基嘧啶、取代苯甲醛与丙二腈的三组分反应合成了4种吡啶并[2,3-d]嘧啶受体分子,利用紫外-可见吸收光谱考察了其与F-,Cl-,Br-,AcO-,等阴离子的作用. 结果表明该类受体分子与阴离子形成氢键配合物,导致吡啶并[2,3-d]嘧啶受体的光谱发生变化. 测定了配合物的结合比和稳定常数,发现受体化合物对AcO-离子具有良好的选择性,对其它多种阴离子无影响. Job曲线表明受体分子与阴离子间形成1:1型的配合物. 1H NMR滴定进一步证实了氢键作用的存在及参与类型.

关键词: 吡啶并[2,3-d]嘧啶, 阴离子识别, 氢键作用

Four new receptors containing pyridio[2,3-d]pyrimidines were synthesized via three-component reaction of 6-aminopyrimidine, substituted benzaldehydes and malononitrile. The properties of the receptors with anions such as F-, Cl-, Br-, AcO-, HSO4- and H2PO4-were examined by UV-Vis spectroscopy. The results showed that receptors have good selectivity to AcO-. However, no obvious changes were observed on the other anions. The Job plot indicated that a 1:1 stoichiometry complex was formed between receptors and anions. The results also showed that hydrogen-bonding interaction was formed between the receptors and anions. The combination assumed above was confirmed by the results of 1H NMR titration.

Key words: pyridio[2,3-d]pyrimidines, anion recognition, hydrogen-bonding interaction