Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 18, Pages 9113-9119Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo401307c
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Funding
- Ministerio de Economia y Competitividad [CTQ2011-22436]
- Xunta de Galicia [PGIDIT10-PXIB209113PR, 2007/085]
- Fundacao para a Ciencia e Tecnologia (FCT) [REEQ/717/QUI/2005]
- FCT (Portugal) [SFRH/BPD/84805/2012]
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p-Sulfonatocalix[4]arene (SC4) interacts with the aromatic dye crystal violet (CV) to form complexes with stoichiometries ranging from SC4:CV = 1:1 up to 1:5 both in solution and in the gas phase. While the 1:1 complex is of the inclusion type, as frequently observed for other guests, in the higher-order complexes the CV molecules interact with SC4 in a peripheral manner. The formation of such complexes is driven by ionic interactions established between the dye and the calixarene and by CV-CV stacking interactions. The application of an advanced fitting procedure made possible a quantitative analysis of the UV-vis data and allowed the determination of the stepwise binding constants. This unprecedented approach provides evidence that the formation of the highest-order complexes occurs through a cooperative mechanism. Moreover, the development of a quantitative analytical model enables the possibility of using this type of system for water-soluble sensing assays, as is also exemplified in the present work.
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