Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation

Abstract

The use of small molecules as chemosensors for ion detection is rapidly gaining popularity by virtue of the advantages it offers over traditional ion sensing methods. Herein we have synthesized a series of acridine(1,8)diones (7a-7l) and explored them for their potential to act as chemosensors for the detection of various anions such as fluoride (F À ), acetate (OAc À ), bromide (Br À ), iodide (I À ), bisulfate (HSO 4 À ), chlorate (ClO 3 À ), perchlorate (ClO 4 À ), cyanide (CN À ), and thiocyanate (SCN À ). Acridinediones were found to be highly selective chemosensors for fluoride ions only. To investigate in detail the mechanism of selective fluoride ion sensing, detailed spectroscopic studies were carried out using UVvisible, fluorescence and 1 H NMR spectroscopy. Fluoride mediated (NH) proton abstraction of acridinedione was found to be responsible for the observed selective fluoride ion sensing. Quantum mechanical computational studies, using time dependent density functional theory (TDDFT) were also carried out, whereupon comparison of acridinedione interaction with fluoride and acetate ions explained the acridinedione selectivity for the detection of fluoride anions. Our results provide ample evidence and rationale for further modulation and exploration of acridinediones as non-invasive chemosensors for fluoride ion detection in a variety of sample types.An oven dried round bottom ask was charged with N-alkyl (Me/ Et) morpholine (1 g, 10 mmol, 1 equiv.) and toluene (5 mL). Subsequently, corresponding alkyl (C 5 , C 7 ) bromide (1.5 equiv.) Fig. 8 Overlay UV-vis absorption spectrum of 7i and fluoride complex 7i-F À , calculated at TD-B3LYP/6-31G(d,p).This journal is

New Hydrogen-Bond-Enriched 1,3,5-Tris(2-hydroxyethyl) Isocyanurate Covalently Functionalized MCM-41: An Efficient and Recoverable Hybrid Catalyst for Convenient Synthesis of Acridinedione Derivatives

“…A series of acridinediones containing aromatic substituents are generally known as antibacterial or antiparasitic agents that are capable of intercalating into DNA base pairs. 63 Furthermore, there are several pharmacological properties associated with these compounds, including antimalarial, 64 antifungal, 65 anticancer, 66 or GCN5 inhibitor 67 properties as well as selective flouride-ion chemosensor 68 and fluorescence enhancement. 69 Due to the biological importance of the acridinedione derivatives, synthesis of these compounds is an interesting research challenge for both organic and medicinal chemists.…”

Receptor‐Spacer‐Fluorophore Based Coumarin‐Thiosemicarbazones as Anion Chemosensors with “Turn on” Response: Spectroscopic and Computational (DFT) Studies

“…And while many such instrument‐based methods exist, the area of small molecule chemosensors for selective fluoride ion detection is relatively under‐explored. A range of different types of molecules having urea, imidazole, pyrrole, indole and thiourea moiety have been reported as chemosensors for various type of anions/cations ,. Thiosemicarbazone moiety, by virtue of having acidic NH protons, shows a very strong binding interaction with small anions particularly F̄ ions.…”

Lansoprazole-Based Colorimetric Chemosensor for Efficient Binding and Sensing of Carbonate Ion: Spectroscopy and DFT Studies

“…The molecular orbital (MO) energy level and distribution of the Lansoprazole was carried out by density functional theory (DFT) calculation at the B3LYP/6-311+G(2d,2p) level (Ishtiaq et al, 2016 ; Iqbal et al, 2018 ; Isaac et al, 2018 ; Islam et al, 2018 ). As we can see from Figure 7 , the electron clouds of LUMO+1, LUMO+2 level of energy for chemosensor L were mainly distributed on the pyridine, and for LUMO level cloud was distributed on the C=N bond of benzimidazole group.…”

“…Developing anionic chemosensors is one of the most important topics nowadays. The optical sensor systems based on light usage as a most valuable and versatile output signal and several chromatographic and fluorogenic anion sensors have been recently established (Fabbrizzi et al, 2001 , 2003 ; Ghorai et al, 2016a ; Iqbal et al, 2018 ; Isaac et al, 2018 ; Wasim et al, 2018 ; Mahmudi et al, 2019 ; Mobed et al, 2019 ). Carbonate is one of these anions which is extensively used in the production of cosmetics, rubber, glass, printing ink, rayon, food, toothpaste, and rechargeable Li-ion batteries (Tas, 2009 ; Zhao et al, 2014 ; Ghorai et al, 2016a ; Kordi et al, 2019 ; Darroudi et al, 2020 ).…”