Abstract
In this study, the synthesis and structure of 4-aminocoumarin derivatives of resorcin[4]arene were investigated. Spectroscopic analysis and quantum mechanical calculations showed that this molecule undertakes a crown-in conformation in chloroform. The conformations of the aminocoumarin derivative of resorcin[4]arene were compared with a hydroxycoumarin derivative of resorcin[4]arene, and the effect of the substituent on the conformational selectivity of the coumarin derivatives of resorcin[4]arene was demonstrated. Both UV-VIS and fluorescence spectroscopy for the coumarin derivative of resorcin[4]arene (3) were performed, and a strong fluorescence quenching of derivative 3 compared to 4-aminocoumarin was observed.
Highlights
New methods for designing and synthesizing supramolecular systems that can be applied to highly functional materials are desirable and applied to macrocyclic compounds, such as cyclodextrins [1], crown ethers [2], pillararenes [3], cucurbitulirs [4], and calixarenes [5]
A conformational analysis was performed based on NMR spectroscopy (CDCl3) observation and by quantum-mechanical calculations
Both experimental and analytical methods suggest the formation of a crown-in type conformation in CHCl3
Summary
New methods for designing and synthesizing supramolecular systems that can be applied to highly functional materials are desirable and applied to macrocyclic compounds, such as cyclodextrins [1], crown ethers [2], pillararenes [3], cucurbitulirs [4], and calixarenes [5]. Calixarenes, which are rigid vase-like molecules, are widespread throughout supramolecular chemistry. Their large-scale synthesis is relatively simple and requires cheap starting materials. They can be selectively functionalised at different positions which render them attractive starting materials from a synthetic standpoint. Resorcin[4]arenes can be functionalised, especially at their upper rim, to provide selective structural, physical, and chemical properties [8]. Functionalised resorcin[4]arenes have been used in supramolecular host–guest (H–G) chemistry [9], nanoparticle synthesis [10], optical [11], chemosensors [12], and for separation applications [13]. Larger supramolecular systems with attractive molecular architecture, such as cavitands [14], carcaplexes [15], dimers [16], and hexamers, have been constructed [17]
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