Jump to main content
Jump to site search

Issue 23, 2020
Previous Article Next Article

Multimode binding and stimuli responsive displacement of acridine orange dye complexed with p-sulfonatocalix[4/6]arene macrocycles

Author affiliations

Abstract

Interaction of acridine orange (AOH+) dye with water soluble anionic p-sulfonatocalix[n]arene (SCXn) hosts, SCX4 and SCX6, having different cavity dimensions, has been investigated using multispectroscopic techniques. Intriguing modulation in the photophysical properties of AOH+ upon interaction with SCXn hosts indicate the formation of different host–guest complexes at different regions of the host concentrations. At lower host concentrations, AOH+ undergoes SCXn assisted aggregation, causing a drastic reduction in fluorescence intensity. At higher host concentrations, aggregated-AOH+–SCXn complexes disintegrate and monomeric-AOH+–SCXn exo and inclusion complexes are eventually formed, leading to a huge fluorescence enhancement finally. Observed effects are more pronounced with SCX6 as compared to SCX4 host. Time-resolved fluorescence studies indicate that at very high host concentrations, there is also a diffusion-controlled dynamic quenching for both monomeric-AOH+–SCXn exo and inclusion complexes, caused by the free SCXn present in the solution, a phenomenon not reported before for such host–guest systems. The aggregated-AOH+–SCXn complexes at lower host concentration were employed to investigate displacement study using an antiviral drug, 1-adamantanamine (AD) and a neurotransmitter, acetylcholine (AcCh), as the competitive binders cum external stimuli, which resulted in a drastic recovery of the fluorescence reduced initially due to aggregation process. Though both the AOH+–SCXn systems act as efficient supramolecular assemblies in sensing AD and AcCh as the analytes through fluorescence “OFF–ON” mechanism, the effect is more pronounced for AOH+–SCX4 system as compared to AOH+–SCX6. SCXn induced interesting modulation in the photophysical properties of AOH+ and the stimulus responsive dye displacement observed for aggregated-AOH+–SCXn systems can expectedly find applications in fluorescence OFF–ON sensing, supramolecular functional materials and similar others.

Graphical abstract: Multimode binding and stimuli responsive displacement of acridine orange dye complexed with p-sulfonatocalix[4/6]arene macrocycles

Back to tab navigation

Supplementary files

Article information


Submitted
03 Jan 2020
Accepted
01 Jun 2020
First published
01 Jun 2020

Phys. Chem. Chem. Phys., 2020,22, 13306-13319
Article type
Paper

Multimode binding and stimuli responsive displacement of acridine orange dye complexed with p-sulfonatocalix[4/6]arene macrocycles

M. Sayed, D. M. Tom and H. Pal, Phys. Chem. Chem. Phys., 2020, 22, 13306
DOI: 10.1039/D0CP00030B

Social activity

Search articles by author

Spotlight

Advertisements