Novel quinoline-derived chemosensors: synthesis, anion recognition, spectroscopic, and computational study†

Authors

Tahira Saleem, Institute of Chemical Sciences, Bahauddin Zakariya University, Multan
Samra Khan, Department of Chemistry, The Women University Multan, Multan
Muhammad Yaqub, Institute of Chemical Sciences, Bahauddin Zakariya University, Multan
Muhammad Khalid, Institute of Chemistry, Khawaja Fareed University of Engineering & Information Technology, Rahim Yar Khan
Muhammad Islam, nstitute of Chemical Sciences, Bahauddin Zakariya University, Multan
Muhammad Yousaf ur Rehman, Institute of Chemical Sciences, Bahauddin Zakariya University, Multan
Muhammad Rashid, Institute of Chemical Sciences, Bahauddin Zakariya University, Multan
Iqra Shafiq, Institute of Chemistry, Khawaja Fareed University of Engineering & Information Technology, Rahim Yar Khan
Ataualpa A. C. Braga, Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo
Asad Syed, Department of Botany and Microbiology, College of Science, King Saud University
Ali H. Bahkali, Department of Botany and Microbiology, College of Science, King Saud University
John F. Trant, Department of Chemistry and Biochemistry, University of Windsor,
Zahid Shafiq, Institute of Chemical Sciences, Bahauddin Zakariya University, MultanFollow

Author ORCID Identifier

https://orcid.org/0000-0002-1899-5689 : Muhammad Khalid

https://orcid.org/0000-0001-7392-3701: Ataualpa Braga

https://orcid.org/0000-0002-2824-7721 : Asad Syed

https://orcid.org/0000-0002-4780-4968 : John F. Trant

https://orcid.org/0000-0003-4088-8297 : Zahid Shafiq

Document Type

Article

Publication Date

8-30-2022

Publication Title

New Journal of Chemistry

Volume

2022

First Page

18233

Last Page

18243

Abstract

Fluorescent-small molecules offer an excellent source of chemosensors when optimized for detection of anions with sensitivity and selectivity, low-cost and robust synthesis. In the present study we synthesized new quinoline-based chemosensors (4a–e) via the one-pot multi component reaction and confirmed their potential for chemosensory via cyclic voltammetry. 4a–e were tested for ligand–anion interaction against F−, OAc−, Br−, ClO3, I−, HSO4−, CN−, ClO4− and SCN-ions, by using UV-visible, colorimetry and Fluorescence. The NH deprotonation was observed as the mechanism of anion interaction via FTIR and H1NMR spectroscopies. Benesi–Hildebrand plot was drawn to calculate binding constants and limit of detection was also computed which showed agreement in theoretical and experimental results. Lastly, computational studies were conducted to investigate the ligand–anion interaction in three-dimensional setting by performing frontier molecular orbital (FMO), UV-Vis, natural bond orbital (NBO) analysis and global reactivity parameters (GRPs) elucidation. Study showed that chemosensors’ chemical reactivity and charge transfer phenomena is explained by the band gap of orbitals. A relatively stable HOMO/LUMO orbitals with grater values of hardness is examined. Further, NBO study described that the intermolecular charge transfer and hyper-conjugation played a significant role in stabilizing the compounds. The findings demonstrated that (4a–e) quinoline-based chemosensors are viable for advance assessment in optimizing excellent chemosensors for fluoride ions.

DOI

10.1039/D2NJ02666J

ISSN

1144-0546

Recommended Citation

Saleem, Tahira; Khan, Samra; Yaqub, Muhammad; Khalid, Muhammad; Islam, Muhammad; ur Rehman, Muhammad Yousaf; Rashid, Muhammad; Shafiq, Iqra; Braga, Ataualpa A. C.; Syed, Asad; Bahkali, Ali H.; Trant, John F.; and Shafiq, Zahid. (2022). Novel quinoline-derived chemosensors: synthesis, anion recognition, spectroscopic, and computational study†. New Journal of Chemistry, 2022, 18233-18243.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/335