Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 40, Pages 12655-12662Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201202438
Keywords
aza-BODIPY; dyes/pigments; photooxidation; singlet oxygen; triplet excited states
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Funding
- Department of Science and Technology (DST), the Government of India
- National Institute for Interdisciplinary Science and Technology (NIIST), CSIR, Trivandrum
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A new series of aza-BODIPY derivatives (4a-4c, 5a, c, and 6b, c) were synthesized and their excited-state properties, such as their triplet excited state and the yield of singlet-oxygen generation, were tuned by substituting with heavy atoms, such as bromine and iodine. The effect of substitution has been studied in detail by varying the position of halogenation. The core-substituted dyes showed high yields of the triplet excited state and high efficiencies of singlet-oxygen generation when compared to the peripheral-substituted systems. The dye 6c, which was substituted with six iodine atoms on the core and peripheral phenyl ring, showed the highest quantum yields of the triplet excited state (Phi(T)=0.86) and of the efficiency of singlet-oxygen generation (Phi(Delta)=0.80). Interestingly, these dyes were highly efficient as photooxygenation catalysts under artificial light, as well as under normal sunlight conditions. The uniqueness of these aza-BODIPY systems is that they are stable under irradiation conditions, possess strong red-light absorption (620-680 nm), exhibit high yields of singlet-oxygen generation, and act as efficient and sustainable catalysts for photooxygenation reactions.
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