Preferential Molecular Encapsulation of an ICT Fluorescence Probe in the Supramolecular Cage of Cucurbit[7]uril and β-Cyclodextrin: An Experimental and Theoretical Approach
- 10 November 2014
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Physical Chemistry B
- Vol. 118 (46), 13279-13289
- https://doi.org/10.1021/jp5079339
Abstract
Supramolecular interaction between an intramolecular charge transfer (ICT) probe, N,N-dimethylaminonaphthyl-(acrylo)-nitrile (DMANAN), and two well-recognized macrocyclic hosts, cucurbit[7]uril (CB7) and β-cyclodextrin (β-CD), has been studied in aqueous medium by absorption, emission, time-resolved measurements, and (1)H NMR spectroscopic methods. The changes in the profiles of the fluorescence spectra illustrate significant modifications in fluorescence intensity, decay time, and quantum yield upon confinement of probe within the hydrophobic cavity of the hosts. Using the Benesi-Hildebrand relationship, the stoichiometric ratio as well as the binding constant of the host-guest complexation has been estimated. The stable inclusion complexes of the probe with different hosts have been supported by DFT and ONIOM based quantum chemical calculations. These methods of measurement establish that the acceptor group of the probe resides inside the hydrophobic cavity of the macrocycle. The competitive binding of metal ions and cationic surfactants to CB7 has been excellently mapped with this guest fluorosensor.Keywords
Funding Information
- University Grants Commission
This publication has 43 references indexed in Scilit:
- Complexation of acridine orange by cucurbit[7]uril and β-cyclodextrin: photophysical effects and pKa shiftsPhotochemical & Photobiological Sciences, 2007
- Cucurbituril Encapsulation of Fluorescent DyesSupramolecular Chemistry, 2007
- Analysis of Host‐Assisted Guest Protonation Exemplified for p‐Sulfonatocalix[4]arene—Towards Enzyme‐Mimetic pKa ShiftsChemistry – A European Journal, 2006
- Photophysical Properties and Rotational Relaxation Dynamics of Neutral Red Bound to β-CyclodextrinThe Journal of Physical Chemistry A, 2004
- Two Mechanisms of Slow Host-Guest Complexation between Cucurbit[6]uril and Cyclohexylmethylamine: pH-Responsive Supramolecular KineticsAngewandte Chemie, 2001
- An Exceedingly Long-Lived Fluorescent State as a Distinct Structural and Dynamic Probe for Supramolecular Association: An Exploratory Study of Host−Guest Complexation by CyclodextrinsJournal of the American Chemical Society, 1999
- Environmental and magnetic field effects on exciplex and twisted charge transfer emissionChemical Reviews, 1993
- The X-ray crystal structure of a 1:1 adduct between α-cyclodextrin and cyclobutane-1,1-dicarboxylatodiammineplationum(II)Journal of the Chemical Society, Chemical Communications, 1985
- The binding of cyclobutane-1,1-dicarboxylatodiamineplatinum(II) by α-cyclodextrin in aqueous solutionJournal of the Chemical Society, Chemical Communications, 1985
- A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic HydrocarbonsJournal of the American Chemical Society, 1949