New naphthoquinone-imidazole hybrids: Synthesis, anion recognition properties, DFT studies and acid dissociation constants

摘要: Abstract The two new naphthoquinone-imidazole based dyes containing indole and pyrene moiety were synthesized their molecular structures confirmed by FT-IR, 1H/13C NMR, HRMS. anion selectivity sensitivity of studied with selected TBA salts in DMSO binary mixture DMSO:Water (1:1, v/v). These interaction mechanisms verified spectrophotometric, spectrofluorometric, 1H NMR titration methods. While the both interact F−, AcO−, CN−, H2PO4− DMSO, only CN− aqueous solution. In addition, experimental results explained DFT calculations. acid dissociation constants determined 25.0 ± 0.1 °C, 0.1 M NaCl ionic strength 40% (v/v) DMSO-Water solution, relating protonated carbonyl group nitrogen atoms for each dye.