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A ketone-functionalized carbazolic porous organic framework for sensitive fluorometric determination of p-nitroaniline

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Abstract

A novel ketone-functionalized carbazolic porous framework named PBPMCz is presented for fluorometric determination of p-nitroaniline (PNA). PBPMCz was prepared by FeCl3-promoted oxidative coupling polymerization of 1,3,5-tris((4-(9H-carbazol-9-yl)phenyl)methanone-1-yl)benzene. The polymer possesses a BET surface area of above 907 m2∙g−1 with a pore volume of 0.72 cm3∙g−1. Compared to the ketone-free framework, the green fluorescence of the probe PBPMCz is more strongly quenched by PNA. Figures of merit include (a) excitation/emission wavelengths of 366/540 nm; (b) a Stern-Volmer constant (Ksv) of 2.2 × 104 M−1, and (c) a detection limit of 1.1 μM. Furthermore, PBPMCz shows different quenching behaviors of PNA compared with o-nitroaniline and m-nitroaniline. The excellent performance of the fluorescent probe is ascribed to the abundant carbazole sites and ketone groups in PBPMCz. These facilitate the electron transfer and hydrogen-bonding interactions between PNA and the polymer.

Schematic presentation of a luminescent carbazolic porous organic framework (CzPOF) modified with keto groups. It shows ultra-sensitivity to quenching by PNA over other nitroaniline isomers.

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Acknowledgements

This work was supported by the financial support from the National Natural Science Foundation of China (Grant Nos. 51703031 and 21401053).

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Authors and Affiliations

  1. College of Materials Science and Engineering, Fuzhou University, Fuzhou, 350108, Fujian, People’s Republic of China

    Li Qian, Haitao Hong, Mingxi Han, Congying Xu & Zhiyong Guo

  2. Hubei Key Laboratory of Low Dimensional Optoelectronic Materials and Devices, Hubei University of Arts and Science, Xiangyang, 441053, Hubei, People’s Republic of China

    Song Wang

  3. Testing Center, Fuzhou University, Fuzhou, 350108, Fujian, People’s Republic of China

    Dan Yan

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  1. Li Qian
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  2. Haitao Hong
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  3. Mingxi Han
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  4. Congying Xu
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  5. Song Wang
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  6. Zhiyong Guo
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  7. Dan Yan
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Correspondence to Zhiyong Guo or Dan Yan.

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Qian, L., Hong, H., Han, M. et al. A ketone-functionalized carbazolic porous organic framework for sensitive fluorometric determination of p-nitroaniline. Microchim Acta 186, 457 (2019). https://doi.org/10.1007/s00604-019-3581-8

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