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

doi:10.6023/cjoc201407012

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2499-2504.DOI: 10.6023/cjoc201407012 Previous Articles Next Articles

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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

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

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).

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

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Zhang Feng, Tan Zan, Yan Boren, Pan Dingwu, Bao Xiaoping. Synthesis of A Novel Carbazole Sulfonohydrazide Receptor Bearing the 1,8-Naphthalimide Units and Its Anion Recognition Properties[J]. Chin. J. Org. Chem., 2014, 34(12): 2499-2504.

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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

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

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