Competitive hydrogen bonding influences of fluorophore- urea-adenine system in water: Photophysical and photochemical approaches

Sumita, Anupurath; Krishnan, Anju; Dhenadhayalan, Namasivayam; Rajaraman, Vasanthi; Rajendran, Kumaran

doi:10.1016/j.saa.2020.118409

Cited by 3 publications

(1 citation statement)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Acridinedione (AD) dyes belong to a class of extrinsic fluorescent probes, wherein enormous studies confined to the photophysical studies in the presence of hydrogen-bonding and hydrophobic solutes have been carried out both in aqueous medium and to a certain extent in nonaqueous solvents. AD dyes act as the host molecule, and the nonfluorophoric solutes such as urea derivatives, guanidine hydrochloride, amides, proteins, amino acids, and sugars behave as the guest molecule. − Furthermore, these dyes exhibit characteristic adsorption, emission, fluorescence lifetime, and oxidation potential properties that are based on the substituents in the ninth and tenth position [Scheme ] and are very much solvent-mediated.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Investigation and Molecular Docking Techniques on the Interaction of Acridinedione Dyes with Water-Soluble Nonfluorophoric Simple Amino Acids

et al. 2021

Self Cite

View full text Add to dashboard Cite

Electrochemical studies of resorcinol-based acridinedione (AD) dyes with nonfluorophoric simple amino acids, glycine, alanine, and valine, were carried out in water. AD probes are classified into photoinduced electron transfer (PET) and non-PET-based dyes, wherein the electrochemical properties and photophysical and photochemical behavior vary significantly based on the nature of substituent groups and the nature of the solute. The oxidation potential of PET dye (ADR1) to that of non-PET-based dye (ADR2) differs significantly such that the addition of amino acids results in a shift of the oxidation peak to a less positive potential and the reduction peak to a lesser negative potential. The extent of shift of oxidation and reduction potential in PET dye is more pronounced than that of non-PET dye on the addition of valine rather than glycine. The variation in the shift is attributed to the presence of an electron-donating moiety (OCH3) group in the ninth position of ADR1 dye. Consequently, the quenching of fluorescence is observed in ADR2 with non fluorophoric amino acids that are authenticated by the shift of the anodic and cathodic peaks toward a lesser positive potential. Molecular docking (MD) studies of PET and non-PET dye with amino acids portray that neither hydrophobic interactions nor electrostatic or weak interactions such as van der Waals and pi–pi interactions govern the electrochemical nature of dye on the addition of amino acids. Furthermore, the formation of a conventional hydrogen bond between dye and amino acid is established from MD studies. The existence of dye–water–amino acid competitive hydrogen-bonding interactions is presumably well-oriented throughout the aqueous phase as observed through photophysical studies which support our electrochemical investigation.

show abstract