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2022 , Vol. 42 >Issue 8: 2551 - 2558

DOI: https://doi.org/10.6023/cjoc202203005

研究论文

碳硼烷基苯并咪唑鎓环蕃的合成及核苷酸识别性质研究

  • 林炳涵 ,
  • 卓继斌 ,
  • 林彩霞 ,
  • 高勇 ,
  • 袁耀锋
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  • a 福州大学化学学院 福州 350108
    b 福建省计量科学研究院 福州 350003
    c 福建师范大学化学与材料科学学院 福州 350117

收稿日期: 2022-03-01

  修回日期: 2022-04-03

  网络出版日期: 2022-04-22

基金资助

国家自然科学基金(21772023); 国家自然科学基金(22071025)

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Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane

  • Binghan Lin ,
  • Jibin Zhuo ,
  • Caixia Lin ,
  • Yong Gao ,
  • Yaofeng Yuan
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  • a College of Chemistry, Fuzhou University, Fuzhou 350108
    b Fujian Metrology Institute, Fuzhou 350003
    c College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350117
* E-mail: ;

Received date: 2022-03-01

  Revised date: 2022-04-03

  Online published: 2022-04-22

Supported by

National Natural Science Foundation of China(21772023); National Natural Science Foundation of China(22071025)

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摘要

以1,2-双(4-苄溴苯基)-邻碳硼烷为原料合成了两种新型的碳硼烷基苯并咪唑鎓类荧光探针4a和4b, 通过IR, 1H NMR, 13C NMR, 11B NMR和ESI-MS对其结构进行表征, 并通过荧光、紫外光谱研究了探针4a和4b对核苷酸的识别性能. 荧光滴定结果表明: 探针4a和4b可以对单磷酸尿苷(UMP)实现on-off型响应, 并具有良好的选择性和灵敏度, 其中探针4b对于UMP的检测限可以达到3.41×10–8 mol/L. 通过Job’s曲线和1H NMR滴定对探针4b的识别机理进行了初步的研究.

关键词： 碳硼烷; 苯并咪唑; 识别; 荧光淬灭; 单磷酸尿苷

本文引用格式

林炳涵 , 卓继斌 , 林彩霞 , 高勇 , 袁耀锋 . 碳硼烷基苯并咪唑鎓环蕃的合成及核苷酸识别性质研究[J]. 有机化学, 2022 , 42(8) : 2551 -2558 . DOI: 10.6023/cjoc202203005

Abstract

Two novel carborane-based benzimidazolium fluorescent probes 4a and 4b were synthesized using 1,2-bis(4-benzylbromophenyl)-o-carborane as starting materials. The structures were characterized by IR, 1H NMR, 13C NMR, 11B NMR and ESI-MS, and the recognition properties of probes 4a and 4b for nucleotides were studied by fluorescence and ultraviolet spectroscopy. The results of fluorescence titration showed that probes 4a and 4b could achieve on-off response to uridine monophosphate (UMP), and had good selectivity and sensitivity. The detection limit of probe 4b for UMP could reach 3.41×10–8 mol/L. The recognition mechanism of the probe 4b was studied by Jobʼs curve and 1H NMR titration.

Key words： carborane; benzimidazole; recognition; fluorescence quenching; uridine monophosphate

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