A bis-benzimidazole PMO ratiometric fluorescence sensor exhibiting AIEE and ESIPT for sensitive detection of Cu.

Xiafan Hao, Shuhua Han, Jingtao Zhu, Yongfeng Hu, Lo Yueh Chang, Chih-Wen Pao, Jeng-Lung Chen, Jin-Ming Chen, Shu-Chih Haw
Author Information
  1. Xiafan Hao: Key Lab of Colloid and Interface Chemistry, Ministry of Education, Shandong University Jinan 250100 P. R. China shuhhan@sdu.edu.cn.
  2. Shuhua Han: Key Lab of Colloid and Interface Chemistry, Ministry of Education, Shandong University Jinan 250100 P. R. China shuhhan@sdu.edu.cn. ORCID
  3. Jingtao Zhu: MOE Key Laboratory of Advanced Micro-structured Materials, School of Physics Science and Engineering, Tongji University Shanghai 200092 P. R. China.
  4. Yongfeng Hu: Canadian Light Source 44 Innovation Boulevard Saskatoon SK S7N 2V3 Canada.
  5. Lo Yueh Chang: Institute of Functional Nano & Soft Materials (FUNSOM), Soochow University-Western University Centre for Synchrotron, Radiation Research Suzhou 215006 P. R. China.
  6. Chih-Wen Pao: National Synchrotron Radiation Research Center 101, Science-Based Industrial Park Hsinchu 30076 Taiwan.
  7. Jeng-Lung Chen: National Synchrotron Radiation Research Center 101, Science-Based Industrial Park Hsinchu 30076 Taiwan.
  8. Jin-Ming Chen: National Synchrotron Radiation Research Center 101, Science-Based Industrial Park Hsinchu 30076 Taiwan. ORCID
  9. Shu-Chih Haw: National Synchrotron Radiation Research Center 101, Science-Based Industrial Park Hsinchu 30076 Taiwan.

Abstract

A novel bis-benzimidazole organic siloxane precursor (BBM-Si) was prepared, and was combined with tetraethylorthosilicate (TEOS) as a mixed Si source. Then, bridged periodic mesoporous organosilica (BBM-PMO) spherical nanoparticles were synthesized by co-condensation using cetyltrimethylammonium bromide (CTAB) as structure directing agent. The optical properties showed that BBM qualifies as an "aggregation induced emission enhanced" (AIEE) molecule, exhibiting characteristics of excited-state intramolecular proton transfer (ESIPT), such as a large Stokes shift and dual fluorescence emission. For the BBM-PMO materials, the silica skeleton provides a rigid environment that limits molecular rotation, resulting in improved fluorescence emission. In particular, the BBM-PMOs exhibited dual emission of the enol and keto forms, achieving a ratiometric response to Cu with high sensitivity and selectivity in a broad pH range. Additionally, the limit of detection was as low as 7.15 �� 10 M in aqueous solution. The X-ray absorption near-edge spectroscopy (XANES) showed the coordination structure through the interaction between copper ions and N atoms of benzimidazole in the BBM-PMO coordinated to Cu. These results demonstrate that BBM-PMO hybrid materials have potential applications in the fields of bio-imaging and environmental monitoring.

References

  1. Chem Commun (Camb). 2015 Oct 4;51(77):14501-4 [PMID: 26280034]
  2. J Fluoresc. 2017 Mar;27(2):745-754 [PMID: 28070795]
  3. J Mater Chem B. 2015 Jul 14;3(26):5182-5188 [PMID: 32262593]
  4. Adv Mater. 2011 Aug 23;23(32):3615-42 [PMID: 21780312]
  5. J Mater Chem B. 2015 Aug 21;3(31):6456-6461 [PMID: 32262553]
  6. Mikrochim Acta. 2018 Feb 19;185(3):188 [PMID: 29594520]
  7. Talanta. 2018 Oct 1;188:708-713 [PMID: 30029436]
  8. J Am Chem Soc. 2011 Nov 9;133(44):17738-45 [PMID: 21957929]
  9. Chem Commun (Camb). 2017 Dec 21;54(2):168-171 [PMID: 29218354]
  10. J Phys Chem A. 2017 Aug 10;121(31):5773-5784 [PMID: 28686446]
  11. Luminescence. 2016 May;31(3):614-25 [PMID: 26910188]
  12. ACS Biomater Sci Eng. 2018 Jan 8;4(1):175-183 [PMID: 33418687]
  13. Faraday Discuss. 2017 Feb 1;196:71-90 [PMID: 27942653]
  14. J Mater Chem B. 2016 Aug 21;4(31):5194-5216 [PMID: 32263600]
  15. Anal Chem. 2011 Apr 15;83(8):3126-32 [PMID: 21425862]
  16. Phys Chem Chem Phys. 2016 Apr 28;18(16):11081-90 [PMID: 27051888]
  17. Environ Sci Technol. 2002 Jul 15;36(14):3050-6 [PMID: 12141481]
  18. Analyst. 2018 Jul 23;143(15):3741-3748 [PMID: 29995040]
  19. ACS Sens. 2018 May 25;3(5):920-928 [PMID: 29667395]
  20. Anal Chem. 2018 Feb 6;90(3):1628-1634 [PMID: 29275622]
  21. Anal Chem. 2013 Jul 2;85(13):6461-8 [PMID: 23745782]
  22. ACS Appl Mater Interfaces. 2014 Sep 24;6(18):16065-70 [PMID: 25153019]
  23. Talanta. 2016 Jan 1;146:575-84 [PMID: 26695306]

Word Cloud

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