Spectroscopic properties and singlet oxygen production by the compound ethyl 3,12-dioxopyran[3,2-a]xanthone-2-carboxylate

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 115; pp. 610 - 616
• Main Authors: da Hora Machado, Antonio Eduardo, Ferreira de Paula, Lucas, de Oliveira-Campos, Ana Maria Ferreira, de Jesus Gomes, Anderson, de Paula, Rodrigo, Barbosa Neto, Newton Martins
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 01-11-2013
• Subjects: Absorption; Computer Simulation; DFT and TD-DFT; Electrons; Emission; PUVA therapy; Quantum Theory; Singlet oxygen; Singlet Oxygen - chemistry; Solvents; Spectrometry, Fluorescence; Static Electricity; Thermodynamics; Xanthone; Xanthones - chemistry; Emission; Xanthone; Absorption; Singlet oxygen; DFT and TD-DFT; PUVA therapy
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2013.06.087

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•The compound ethyl 3,12-dioxopyran[3,2-a]xanthone-2-carboxylate was studied.•This study involved experimental measurements and quantum-mechanical calculations.•Spectroscopic and quantum-mechanical data agree very well.•High efficiency in the generation of singlet oxygen.•This compound can be a promising phototherapeutic agent for PUVA therapy.
The steady state and time resolved experiments together with absorption and emission spectroscopies and quantum chemical calculations have been employed to investigate spectroscopic properties of a xanthone-type compound (ethyl 3,12-dioxopyran[3,2-a]xanthone-2-carboxylate). The spectroscopic data show good agreement with results obtained from quantum chemical calculations. Additionally, this compound shows expressive quantum efficiency for triplet population and a quantum efficiency of singlet oxygen generation very close to unity. Correlations between the nature of singlet and triplet excited states and spectroscopic properties were performed in order to understand the high quantum efficiency of singlet oxygen generation by this compound.