Effect of hydrogen bonding interaction on the photophysics of α-amino-orcein

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
C ClementiFausto Elisei

Abstract

This paper reports for the first time a detailed spectroscopic investigation into the ground- and excited-state properties of α-amino-orcein (α-AO), one of the main components of the orcein dye, in solvents of different proticity and water at different pHs. In order to gain insight into the nature of the involved transitions and excited state deactivation pathways, the study was carried out by means of UV-Visible steady state and ultrafast spectroscopic techniques with the support of quantum mechanical calculations (DFT and TDDFT). The results highlight that the photophysical and photodynamic behaviour of α-AO are highly sensitive to the solvent proticity and pH. In particular, protic environment induces a red shift (55 nm) of the absorption spectrum together with a relevant decrease of the fluorescence quantum yield (from 0.19 in acetonitrile to 6.6 × 10-3 in methanol) and radiative rate constant (two orders of magnitude). A notable red shift is also caused by increasing the pH leading the molecule from monocationic to neutral and then monoanionic form through two deprotonation steps (pKa = 3.539 ± 0.006 and 11.180 ± 0.006). Following deprotonation, the molecule assumes spectral and photophysical properties very similar to tho...Continue Reading

Citations

Jul 14, 2021·Physical Chemistry Chemical Physics : PCCP·Catia ClementiFrancesca Nunzi

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