A Calix[4]arene-Functionalized Perylene Imide and Its Luminescence Properties

In this study, new perylene-derived molecules were synthesized as perylene-3,4,9,10-tetracarboxylic acid monoanhydride monopotassium carboxylate 1; N-(3-propanol)perylene-3,4,9,10-tetracarboxylic-3,4-(monoimide)anhydride-9,10-acid potassium carboxylate 2; 5,11,17,23-tetra(tert-butyl)-25,27-bis(3 ’ -bromopropoxy)-26,28-(dihydroxy)calix[4]arene 3; 5,11,17,23-tetra(tert)butyl)-25-(3 ’ -bromopropoxy)-27-(N-[3 ’ (3 ’ -propoxy)propyl]perylene-(3 ’ ,4 ’ ,9 ’ ,10 ’ -tetracarboxylic-3 ’ ,4 ’ -(monoimide)anhydride-9 ’ ,10 ’ -acid potassium carboxylate)-26,28-(dihydroxy)calix[4]arene 4. They were characterized by nuclear magnetic resonance (1H NMR, 1H-1H correlation spectroscopy (COSY), 1H-13C heteronuclear single quantum coherence spectroscopy (HSQC), 1H-13C heteronuclear multiple bond correlation (HMBC)), Fourier transform infrared (FTIR), UV-Vis, and luminescence spectroscopies, besides elemental analysis. Cyclic voltammetry and spectroelectrochemical behavior techniques showed a well-defined one-electron reversible process. The compounds have high emission quantum yield and are very stable electron-receptors. Ligand 4 has a broad emission shifted to 540 nm based on its precursor 2, shown at 531 nm. However, ligand 4 ( φ = 0.31) depicted a quantum yield lower than compound 2 ( φ = 0.57), indicating that association with calixarene slightly decreases quantum yield. Nevertheless, it improves solubility significantly in organic solvents, which renders it usef...
Source: Journal of the Brazilian Chemical Society - Category: Chemistry Source Type: research