Chuchawin Changtong1, Christopher Schuster1, John L. Lombardi2, and Robert E. Connors1. (1) Worcester Polytechnic Institute, Worcester, MA, (2) Ventana Research Corporation, South Tucson, AZ
It is well known that excited singlet oxygen (
1Δ
g) shows chemical reactivity that differs significantly from that of ground state molecular oxygen (
3Σ
g-). This has led to a range of applications that include photodynamic therapy, novel chemical synthesis, and chemical/biological decontamination. Singlet oxygen is commonly generated by energy transfer from a photosensitizer. Previous work has established that a number of organic ring compounds are capable of reversibly trapping and storing singlet oxygen with high efficiency. These storage molecules decompose to the original molecule by releasing oxygen in the reactive singlet form. This work describes the preparation and characterization of composite molecules that have several singlet oxygen storage moieties bonded directly to a photosensitizer dye. These materials, under the action of light and ambient oxygen, have the capacity to generate, trap, and release singlet oxygen.
1H-NMR reveals that this cycle can be repeated a number of times without detectable degradation or formation of side products. Unlike conventional photosensitizers, the reversible storage capacity of these materials ensures that singlet oxygen will continue to be produced after the source of light has been removed. Kinetic and spectroscopic properties will be discussed.
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