A study of the interaction between inverted cucurbit[7]uril and symmetric viologens

Abstract

The interaction between inverted cucuribit [7]uril (iQ [7]) and a series of symmetric viologen derivatives bearing aliphatic substituents of variable length, namely dicationic dialkyl-4,4 0 -bipyridinium guests where the alkyl is CH 3 (CH 2 ) n with n ¼ 0 to 6, has been studied in aqueous solution by

A New Member of the Inverted Cucurbit[n]uril Family

“…In addition, the interaction between i Q[7] and 2N2 was found to be dominated by a portal interaction, whereas an inclusion interaction model dominated in the Q[7]‐ 2N2 interaction system . More recently, Xiao and co‐workers reported a series of interaction of i Q[6] and i Q[7] with various guests and metal ions, amongst i Q[7] can easily form dumbbell‐type host–guest supramolecular assemblies with dicationic dialkyl or dipenzyl‐4,4′‐bipyridiniums, the binding interactions between i Q[7] and 10 essential l ‐α‐amino acid guests not only enhance our knowledge of the molecular recognition of amino acids but may also be of significance for the design and synthesis of new macrocyclic compounds for biological identification and simulation …”

Solvent Effects on the Spectral and Electrochemical Properties of Some Pyridinium Quaternary Compounds

“…* email: rboscencu@yahoo.com Several other N-heterocyclic compounds have been reported in the literature and found to behave as efficient electron acceptors. These species share the nature of electron-poor p-systems but possess quite distinct physicochemical properties [16]. There is a range of the redox potentials values for viologens reported in literature [17,18] and many of them confirm the biological applications.…”

Binding and Selectivity of Essential Amino Acid Guests to the Inverted Cucurbit[7]uril Host

“…33−35 To investigate the host–guest chemistry of the iQ[7], we investigated the binding interaction of an inverted cucurbit[7]uril with α,ω-alkyldiammonium guests 36 and 4,4′-bipyridine derivatives. 37,38 In a continuation of this research, herein, we explored the binding of essential amino acids to the iQ[7] host to expand our knowledge of the supermolecular chemistry of iQ[ n ]s. We studied the binding interactions of iQ[7] with 10 essential amino acids (Scheme 1) in buffered solution by 1 H NMR spectroscopy, isothermal titration calorimetry (ITC), and matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS). Meanwhile, we also characterized the interaction between iQ[7] and basic amino acids at pD = 3 by 1 H NMR spectroscopy.…”

“…In 2005, Isaacs and Kim reported the isolation, characterization, and recognition properties of inverted cucurbit­[ n ]­urils (iQ­[ n ]­s, where n = 6 and 7), and some related properties of iQ­[ n ]­s were also described. − However, to date, few reports have focused on the newest member of the Q­[ n ]­s, iQ[7]. Our group studied the coordination chemistry of an iQ[7] with a series of metal ions. − To investigate the host–guest chemistry of the iQ[7], we investigated the binding interaction of an inverted cucurbit[7]­uril with α,ω-alkyldiammonium guests and 4,4′-bipyridine derivatives. , In a continuation of this research, herein, we explored the binding of essential amino acids to the iQ[7] host to expand our knowledge of the supermolecular chemistry of iQ­[ n ]­s. We studied the binding interactions of iQ[7] with 10 essential amino acids (Scheme ) in buffered solution by 1 H NMR spectroscopy, isothermal titration calorimetry (ITC), and matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS).…”