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

Author(s)

Giulia Murbach-Oliveira ; Izilda A. Bagatin ^[2]

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 31, n. 11, p. 2385-2395, 2020-10-30.

Abstract

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 useful for applications in the development of organic light-emitting diode (OLEDs) or biological markers. (AU)

• FAPESP's process: 15/20485-4 - Calixarenes and iminic ligands developed for sensors, luminescent and bioinorganic compounds
• Grantee: Izilda Aparecida Bagatin
• Support Opportunities: Regular Research Grants
• FAPESP's process: 17/15083-0 - Studies and Application of luminescent compounds based on calix[4]arenes
• Grantee: Giulia Murbach de Oliveira
• Support Opportunities: Scholarships in Brazil - Scientific Initiation