Resonance-assisted hydrogen bonding induced nucleophilic addition to hamper ESIPT: ratiometric detection of cyanide in aqueous media

Abstract

For ratiometric "naked eye" detection of CN(-), an ESIPT exhibiting benzothiazole receptor (BHI) is designed having one aldehyde group ortho and the other aldehyde para to the OH group respectively. Due to RAHBs, the ortho aldehyde group is highly reactive undergoing nucleophilic cyanide addition selectively, which hampered ESIPT. This is also supported by DFT and TD-DFT calculations.

Interplay of micro- and macroscopic solvation in spectral responses of PACO in 1,4-dioxane–water mixtures: A combined experimental and quantum chemical analysis

“…Secondly, the polar solvent molecules can surround the polar probe leading to what is known as dielectric enrichment [6][7][8][9]. The site specific interaction, that is, the hydrogen-bonding interaction controls the structure and reactivities of many chemical and biological processes [10][11][12][13][14][15][16][17][18][19][20][21]. The molecule under investigation, 3-(phenylamino)-2-cyclohexen-1-one, abbreviated as PACO (Scheme 1) is one of the recently studied molecules that shows RAHB in the excited state [22].…”

Fluorogenic ratiometric dipodal optode containing imine-amide linkages: Exploiting subtle thorium (IV) ion sensing

“…The interest in the development of sensors is due to the apprehension related to perilous effect of these ions on the environment and also due to their adverse effects on physiological processes when they exceed the cellular needs [6][7][8][9]. The reported sensors reveals that now a day noncyclic compounds having array of binding sites for noncovalent interactions are converging for complexation towards respective cationic/anionic or neutral substances.…”

A fluorescent probe for alkaline phosphatase via excited state intramolecular proton transfer

“…And this technique has been extensively applied in the research of various enzyme-catalyzed processes [51][52][53][54][55]. [56][57][58][59][60][61][62][63][64][65][66][67]. In comparison with the other fluorescent processes, such as electron transfer and energy transfer, ESIPT process can occur at a much faster rate [68].…”