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Synthesis of BIII Suboxochlorins
Xiaorong Jin1, Boyu Xiao1, Yutao Rao1
1Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China.
Abstract:
As a new core-modified variant of BIII subporphyrins, BIII suboxochlorins were synthesized from BIII meso-2-formylphenylsubporphyrins via addition reaction with mesitylmagnesium bromide, Friedel-Crafts type cyclization effected with BF3·OEt2, and oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or AgPF6. The synthesized BIII suboxochlorins are equipped with a fused and conjugated benzocyclohexene unit at the periphery and display broad and blue-shifted Soret bands and red-shifted and vibronic structured Q-bands as compared with the usual BIII triarylsubporphyrins. These BIII suboxochlorins emit fluorescence, showing a peak over 700 nm and a tail reaching 1000 nm with ca. 2.8% quantum yield.
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