Hydrogen bonding effects in the photophysics of a drug, Piroxicam, in homogeneous media and dioxane–water mixtures

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Publication Date
DOI 10.1039/A906213K
Impact Factor 3.676
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Abstract

The fluorescence emission of Piroxicam, an anti-inflammatory drug exhibiting excited-state intramolecular proton transfer (ESIPT), was studied in pure solvents and in dioxane–water mixtures. The solvent proticity was seen to play a key role in the ground-state promoting the existence of different conformers (open and closed form), and in the excited-state where it is responsible for a pronounced quenching of the tautomer emission in the aforementioned mixtures. A derived Stern–Volmer relation shows the diffusive control of the process (kq≈4.3×109 M-1 s-1). The values of polarity (π*), proticity (α) and ET(30) of dioxane–water mixtures assessed by the solvatochromism of this molecule, are in agreement with a “critical’' concentration ≈22 M above which water presents the characteristics of the free solvent. Below that concentration, Piroxicam adopts a closed conformation through an intramolecular hydrogen bond in a six-membered ring, which is very stable and thus insensitive to microenvironmental changes.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
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Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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