Solvent Dependence of the Photophysical Properties of 2-Chlorothioxanthone, the Principal Photoproduct of Chlorprothixene

Authors

  • Luis E. Piñero Santiago,

    1. Instituto de Tecnología Química UPV-CSIC, Universidad Politécnica de Valencia, Avenida de los Naranjos, Valencia, Spain
    2. Department of Chemistry, University of Puerto Rico at Humacao, Humacao, Puerto Rico
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  • Carmelo García,

    Corresponding author
    1. Department of Chemistry, University of Puerto Rico at Humacao, Humacao, Puerto Rico
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  • Virginie Lhiaubet-Vallet,

    1. Instituto de Tecnología Química UPV-CSIC, Universidad Politécnica de Valencia, Avenida de los Naranjos, Valencia, Spain
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  • Miguel A. Miranda,

    Corresponding author
    1. Instituto de Tecnología Química UPV-CSIC, Universidad Politécnica de Valencia, Avenida de los Naranjos, Valencia, Spain
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  • Rolando Oyola

    1. Department of Chemistry, University of Puerto Rico at Humacao, Humacao, Puerto Rico
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Corresponding authors email: carmelo.garcia@upr.edu (Carmelo García); mmiranda@qim.upv.es (Miguel A. Miranda)

Abstract

2-chlorothioxanthone (CTX) is used as photoinitiator for the reticulation of synthetic resins and for the preparation of pharmaceuticals. It was previously determined that CTX is the primary photoproduct of z-chlorprothixene (CPTX) when irradiated at 313 nm and is formed in an autocatalyzed reaction through an energy-transfer mechanism (Piñero et al. [2009] Photochem. Photobiol., 85, 895–900). In this work, the photophysical properties of CTX were measured in acetonitrile/water solutions to determine if their magnitude can affect the side effects of CPTX. The results show that CTX has higher absorption coefficients in the visible region (400–420 nm) and higher triplet quantum yields than its parent compound. Similar to TX, both properties strongly depend on the solvent polarity/hydroxylicity. The quantum yield of the triplet intermediate is very close to the value of the phenothiazine triplets. The phenothiazines are the most phototoxic antidepressants. Therefore, given the appropriate microenvironment, the photosensitization side effects of CPTX can be intensified on the production of CTX.

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