Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane

doi:10.6023/cjoc202203005

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2551-2558.DOI: 10.6023/cjoc202203005 Previous Articles Next Articles

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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^a, 卓继斌^b, 林彩霞^a, 高勇^a^,^c^,^*(), 袁耀锋^a^,^*()

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 发布日期:2022-09-06
通讯作者: 高勇, 袁耀锋
基金资助:
国家自然科学基金(21772023); 国家自然科学基金(22071025)

Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane

Binghan Lin^a, Jibin Zhuo^b, Caixia Lin^a, Yong Gao^a^,^c(), Yaofeng Yuan^a()

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

Received:2022-03-01 Revised:2022-04-03 Published:2022-09-06
Contact: Yong Gao, Yaofeng Yuan
Supported by:
National Natural Science Foundation of China(21772023); National Natural Science Foundation of China(22071025)

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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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Binghan Lin, Jibin Zhuo, Caixia Lin, Yong Gao, Yaofeng Yuan. Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2551-2558.

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Fig. & Tab. 8

Scheme 1. Synthesis of probes 4a and 4b

Figure 1. Fluorescence emission spectra of probes 4a and 4b (10 μmol/L) in the presence of different nucleotdes (100 μmol/L) (a, b); Comparison of fluorescence intensity of 4a and 4b (10 μmol/L) at the maximum emission wavelength of 367 nm in the absence and presence of single nucleotides (100 μmol/L) (c, d)

Figure 2. (a) Fluorescence emission spectra of different concentration of UMP (100 μmol/L) added to the solution of probe 4a (10 μmol/L) (Inset: the B-H equation of 4a complexed with UMP and fluorescence quenching exposed to 254 nm light); (b) Fluorescence emission spectra of different concentration of UMP (80 μmol/L) added to the solution of probe 4b (10 μmol/L) (Inset: the B-H equation of 4b complexed with UMP and fluorescence quenching exposed to 254 nm light)

Figure 3. (a) Anti-interference ability of probe 4a to UMP in the presence of different monophosphate nucleotides or anions; (b) anti-interference ability of probe 4b to UMP in the presence of different monophosphate nucleotides or anions

Figure 4. Job’s plot between the probe 4a or 4b and UMP

Figure 5. 1H NMR spectra of different concentration of UMP added to 4b solution

Scheme 2. Proposed mechanism of probe 4b interacted with UMP

主体	客体	K/(L•mol^–1)	检测限/(mol•L^–1)
4a	UMP	2.87×10³	7.62×10^–7
4b	UMP	2.81×10⁴	3.41×10^–8

Table1. Recognition performance of probes 4a and 4b for UMP

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碳硼烷基苯并咪唑鎓环蕃的合成及核苷酸识别性质研究

Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane

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