Performance of 4,5‐diphenyl‐1H‐imidazole derived highly selective ‘Turn‐Off’ fluorescent chemosensor for iron(III) ions detection and biological applications

Abstract

AbstractTwo fluorescent chemosensors, denoted as chemosensor 1 and chemosensor 2, were synthesized and subjected to comprehensive characterization using various techniques. The characterization techniques employed were Fourier‐transform infrared (FTIR), proton (1H)‐ and carbon‐13 (13C)‐nuclear magnetic resonance (NMR) spectroscopy, electrospray ionization (ESI) mass spectrometry, and single crystal X‐ray diffraction analysis. Chemosensor 1 is composed of a 1H‐imidazole core with specific substituents, including a 4‐(2‐(4,5‐c‐2‐yl)naphthalene‐3‐yloxy)butoxy)naphthalene‐1‐yl moiety. However, chemosensor 2 features a 1H‐imidazole core with distinct substituents, such as 4‐methyl‐2‐(4,5‐diphenyl‐1H‐imidazole‐2‐yl)phenoxy)butoxy)‐5‐methylphenyl. Chemosensor 1 crystallizes in the monoclinic space group C2/c. Both chemosensors 1 and 2 exhibit a discernible fluorescence quenching response selectively toward iron(III) ion (Fe3+) at 435 and 390 nm, respectively, in dimethylformamide (DMF) solutions, distinguishing them from other tested cations. This fluorescence quenching is attributed to the established mechanism of chelation quenched fluorescence (CHQF). The binding constants for the formation of the 1 + Fe3+ and 2 + Fe3+ complexes were determined using the modified Benesi–Hildebrand equation, yielding values of approximately 2.2 × 103 and 1.3 × 104 M−1, respectively. The calculated average fluorescence lifetimes for 1 and 1 + Fe3+ were 2.51 and 1.17 ns, respectively, while for 2 and 2 + Fe3+, the lifetimes were 1.13 and 0.63 ns, respectively. Additionally, the applicability of chemosensors 1 and 2 in detecting Fe3+ in live cells was demonstrated, with negligible observed cell toxicity.