Abstract
In this work, we describe the synthesis of a novel 9-aminoacridine derivative that presents surprisingly different colors when exposed to neutral, acidic or basic mediums with potential application as pH indicator in organic solvents. Furthermore, pKa and molar absorptivity values were determined and theoretical studies supported by density functional theory (DFT) calculations were performed to elucidate the different structures of this compound.
Highlights
9-Aminoacridine (9-AA) is a polycyclic heteroaromatic compound with three fused rings that can be used as specific fluorescent.[1,2] Its derivatives, which have fluorescence properties and are typically colored, have a wide range of applications such as biological activity[3] against neurodegenerative diseases and protozoal parasites.[4]
The anticancer effect of nitro-9-aminoacridine derivatives is reported in the literature.[5,6]
The mass of the molecular ion was identified through analysis by matrix assisted laser desorption/ionization - time of flight mass spectrometer (MALDI-TOF MS) using a pulsed nitrogen ultraviolet laser (λ = 337 nm) of an AXIMA Performance MALDI-TOF MS (Shimadzu Biotech, Japan)
Summary
9-Aminoacridine (9-AA) is a polycyclic heteroaromatic compound with three fused rings that can be used as specific fluorescent.[1,2] Its derivatives, which have fluorescence properties and are typically colored, have a wide range of applications such as biological activity[3] against neurodegenerative diseases and protozoal parasites.[4]. The pKa value is an important physicochemical parameter to predict the ionization state of a substance for the measurements of pH-dependent molecular properties (solubility and lipophilicity, for example). In this work, it was synthesized the compound 2,4,5,7-tetranitro-9-aminoacridine (TNA), introducing four nitro groups in the aromatic rings of 9-AA (Figure 1), and the new derivative presented different colorations when exposed to neutral, acidic or basic mediums. We performed a potentiometric titration to determine its pKa values in different mediums and we confirmed the structures present in each medium through density functional theory (DFT) calculations
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