Development of AIE active carbazole based fluorescent probe for rapid detection of 4-nitrotoluene in solution and solid phases: experimental and DFT insights
- 1Department of Chemistry, Faculty of Science, King Khalid University P.O. Box 960 Abha 61421 Saudi Arabia
- 2Department of Chemistry, COMSATS University Islamabad Abbottabad Campus, University Road Abbottabad 22060 Pakistan
- 3School of Mathematical and Physical Sciences, Faculty of Science, University of Technology Sydney Sydney New South Wales Australia
Abstract
A fluorescent probe CPT has been strategically designed and synthesized via Ullmann and Claisen–Schmidt condensation reactions, and its photophysical properties were systematically investigated. Aggregation-induced emission (AIE) with a 25 nm hypsochromic shift, was attributed to aggregate formation. Further, probe CPT exhibited distinct solvatochromic behavior with a 31 nm bathochromic shift. Owing to these unique optical properties, probe CPT serves as an efficient sensing tool for 4-nitrotoluene (4-NT), exhibiting a fluorescence-quenching response via a twisted intramolecular charge transfer (TICT) and photoinduced electron transfer (PET) mechanism. Probe CPT exhibited a hypsochromic shift of 39 nm upon treating with 4-NT. The interaction mechanism was investigated using 1H NMR, FTIR, mass spectrometry titration, DLS, and DFT calculations. CPT exhibited excellent selectivity and high sensitivity toward 4-NT, with an LOD of 0.16 nM and an LOQ of 0.55 nM. Furthermore, probe CPT exhibited remarkable efficacy in solid and solution-phase sensing of 4-NT, highlighting its potential applicability for monitoring 4-NT in real industrial effluents.
Related
- Tyrosinase–SWCNT Electrochemical Biosensor for Tyramine Detection: Experimental Development and Molecular Dynamics Insights
- A bifunctional ER-targeting fluorescent probe for the detection of SO2 and polarity in living cell and animals
- Rapid detection of major Gram-positive pathogens in ocular specimens using a novel fluorescent vancomycin-based probe
- A multi-valent polymyxin-based fluorescent probe for the detection of Gram-negative infections
- Recent Advances in Near-Infrared Fluorescent Probes Based on Organic Small Molecules for the Detection and Imaging of Heavy Metal Ions
BibTeX
@article{alarfaji2026development,
title = {{Development of AIE active carbazole based fluorescent probe for rapid detection of 4-nitrotoluene in solution and solid phases: experimental and DFT insights}},
author = {Saleh S. Alarfaji and Alam Shabbir and Huda Khalid and Qudsia Sajid and Asad Muhammad Khan and Umar Farooq and Sohail Anjum Shahzad},
journal = {RSC Advances},
year = {2026},
month = nov,
doi = {10.1039/d6ra08681k},
url = {https://doi.org/10.1039/d6ra08681k},
note = {CC BY 3.0},
}
RIS
TY - JOUR
TI - Development of AIE active carbazole based fluorescent probe for rapid detection of 4-nitrotoluene in solution and solid phases: experimental and DFT insights
AU - Saleh S. Alarfaji
AU - Alam Shabbir
AU - Huda Khalid
AU - Qudsia Sajid
AU - Asad Muhammad Khan
AU - Umar Farooq
AU - Sohail Anjum Shahzad
PY - 2026
DA - 2026/11/04
JO - RSC Advances
DO - 10.1039/d6ra08681k
UR - https://doi.org/10.1039/d6ra08681k
AB - A fluorescent probe CPT has been strategically designed and synthesized via Ullmann and Claisen–Schmidt condensation reactions, and its photophysical properties were systematically investigated. Aggregation-induced emission (AIE) with a 25 nm hypsochromic shift, was attributed to aggregate formation. Further, probe CPT exhibited distinct solvatochromic behavior with a 31 nm bathochromic shift. Owing to these unique optical properties, probe CPT serves as an efficient sensing tool for 4-nitrotoluene (4-NT), exhibiting a fluorescence-quenching response via a twisted intramolecular charge transfer (TICT) and photoinduced electron transfer (PET) mechanism. Probe CPT exhibited a hypsochromic shift of 39 nm upon treating with 4-NT. The interaction mechanism was investigated using 1H NMR, FTIR, mass spectrometry titration, DLS, and DFT calculations. CPT exhibited excellent selectivity and high sensitivity toward 4-NT, with an LOD of 0.16 nM and an LOQ of 0.55 nM. Furthermore, probe CPT exhibited remarkable efficacy in solid and solution-phase sensing of 4-NT, highlighting its potential applicability for monitoring 4-NT in real industrial effluents.
SN - 2046-2069
ER -