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.
Highlights
Calixarenes are macrocycles resulting from the condensation of p-substituted phenols and formaldehyde groups.[1,2] A wide range of synthesis strategies arise from the possibilities of functionalization and combination of phenolic groups, as well as of association between different calixarenes
New applications have been outlined for calixarenes, such as fluorescent biological markers and in light-emitting devices,[7,8,9,10] as the OLEDs, organic light-emitting diodes
Ligand 4 is soluble in organic solvents
Summary
Calixarenes are macrocycles resulting from the condensation of p-substituted phenols and formaldehyde groups.[1,2] A wide range of synthesis strategies arise from the possibilities of functionalization and combination of phenolic groups, as well as of association between different calixarenes. As both upper and lower calixarene rims can be functionalized with various groups, the introduction of one group to the aromatic ring could alter its reactivity, and planning is required to respect this condition.[3] due to these numerous possibilities, some properties are commonly observed, such as high melting points; low solubility in water, good solubility in organic solvents; excellent flexibility and different cavity sizes; possibility of forming coordination compounds with metals and neutral molecules; well-defined oligomers and thermal stability.[1]. As a result of their structure associated with different functionalizations and their physicochemical properties, calixarenes are considered for an assortment of industrial applications, such as stabilizers for organic polymers and neutral organic molecules separation,[4,5] besides the already observed selective complexes formation with certain metals, as hazardous metal sequestrations such as uranium and cesium, phase transfer agents, accelerators for instant adhesives, Langmuir-Blodgett films membranes, and catalysts.[4,5,6] In addition to these, new applications have been outlined for calixarenes, such as fluorescent biological markers and in light-emitting devices,[7,8,9,10] as the OLEDs, organic light-emitting diodes
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