Cooperative Assembly of Discrete Stacked Aggregates Driven by Supramolecular Host-Guest Complexation

Nuno Basílio, Luis García-Río

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

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.}
Original languageEnglish
Pages (from-to)9113-9119
JournalJournal of Organic Chemistry
Volume78
Issue number18
DOIs
Publication statusPublished - 20 Sep 2013

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