有机化学 ›› 2014, Vol. 34 ›› Issue (12): 2499-2504.DOI: 10.6023/cjoc201407012 上一篇    下一篇

研究论文

含1,8-萘酰亚胺单元的咔唑磺酰肼受体的合成及对阴离子的识别研究

张峰, 谭赞, 闫柏任, 潘顶伍, 鲍小平   

  1. 贵州大学精细化工研究开发中心 绿色农药与农业生物工程国家重点实验室培育基地 教育部绿色农药与农业生物工程重点实验室 贵阳 550025
  • 收稿日期:2014-07-09 修回日期:2014-08-18 发布日期:2014-08-29
  • 通讯作者: 鲍小平 E-mail:baoxp_1980@aliyun.com
  • 基金资助:

    国家自然科学基金(No.21161005)资助项目.

Synthesis of A Novel Carbazole Sulfonohydrazide Receptor Bearing the 1,8-Naphthalimide Units and Its Anion Recognition Properties

Zhang Feng, Tan Zan, Yan Boren, Pan Dingwu, Bao Xiaoping   

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
  • Received:2014-07-09 Revised:2014-08-18 Published:2014-08-29
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21161005).

设计合成了一个新型的含1,8-萘酰亚胺信号单元的咔唑磺酰肼类阴离子受体1, 荧光和UV-vis光谱滴定实验表明, 1在DMSO中能选择性识别具有重要生物学意义的F-, AcO-和H2PO4-; 受体1与这些阴离子形成1:1的配合物, 且它们的结合常数均大于103 L·mol-1. 有趣的是, 在含水10% (V/V)的DMSO中1对F-表现出了专一性识别. DMSO-d6中的核磁滴定表明, 在F-浓度较低时, 受体1通过五重分子间氢键作用与其产生了有效结合.

关键词: 咔唑, 磺酰肼, 1,8-萘酰亚胺, 阴离子识别

A novel carbazole sulfonohydrazide receptor (1) bearing the 1,8-naphthalimide units was designed and synthesized, which selectively recognized biologically important F-, AcO- and H2PO4- in DMSO, as evidenced by fluorescence and UV-vis titration experiments. Receptor 1 formed 1:1 complexes with these anions, affording the binding constants larger than 103 L·mol-1. Interestingly, receptor 1 displayed a specific recognition towards F- in DMSO containing 10% H2O (V/V). The 1H NMR titration experiments in DMSO-d6 proved that five-fold intermolecular H-bonding interactions were responsible for effective complexation between 1 and F- (at a low concentration).

Key words: carbazole, sulfonohydrazide, 1,8-naphthalimide, anion recognition