Abstract
Three new 2-component unsubstituted ( 4P ), diiodo- ( 5P ), and dibromo- ( 6P ) distyryl-BODIPY-bridged cyclotriphosphazene dimers were designed and synthesized. The newly synthesized BODIPY-cyclotriphosphazene systems were characterized by 1 H, 13 C, and 31 P NMR spectroscopy. The photophysical properties of the distryl-BODIPYs (4–6) and BODIPY-cyclotriphosphazene dyads ( 4P – 6P ) were studied by UV-Vis absorption and fluorescence emission spectroscopy. In these derivatives, the bino-type cyclotriphosphazene derivative bearing unsubstituted BODIPY unit 4P exhibited high fluorescence and no singlet oxygen generation due to the lack of spin converter. The attachment of heavy atoms (iodine and bromine) enabled the production of singlet oxygen. The bino-type BODIPY-cyclotriphosphazenes ( 5P and 6P ) were also used as triplet photosensitizers in the photooxidation of 1,3-diphenylisobenzofuran to endoperoxide via generation of the singlet oxygen in dichloromethane. The singlet oxygen production of these compounds was also investigated via a direct method and produced a singlet oxygen phosphorescence peak at 1270 nm.
Highlights
Phosphazenes are one of the most studied classes of inorganic heterocyclic molecules [1]
Synthesis and structural characterization The synthetic pathways to prepare the BODIPYs (4–6) and BODIPY-bridged cyclotriphosphazenes (4P–6P) in this study are shown in the Scheme
BODIPYs (4–6) in tetrahydrofuran solutions were reacted with an excess of hexachlorocyclotriphosphazene in the presence of Cs 2 CO 3 to prepare BODIPY-bridged cyclotriphosphazenes (4P–6P) from nucleophilic displacement reactions
Summary
Phosphazenes are one of the most studied classes of inorganic heterocyclic molecules [1] The significance of this class is due to their wide application areas, such as medicine, biology, flame-retardant additives, membranes, microlithography, and ionic crystals [2,3,4,5]. In these studies, cyclotriphosphazenes are widely used as a core platform to develop tailor-made systems, because cyclotriphosphazene can be tuned by nucleophilic substitution reactions [6]. The photophysical properties of BODIPYs (4–7) and BODIPY-bridged cyclotriphosphazenes (4P–6P) were studied via UV-Vis and fluorescence emission techniques. Singlet oxygen generation abilities of BODIPY-bridged cyclotriphosphazenes (4P–6P) were investigated via both indirect and direct methods
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