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Synthesis and spectroscopic properties of ?-triazoloporphyrin-xanthone dyads.

ABSTRACT: A novel series of ?-triazoloporphyrin-xanthone conjugates and xanthone-bridged ?-triazoloporphyrin dyads has been synthesized in moderate to good yields through Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of copper(II) 2-azido-5,10,15,20-tetraphenylporphyrin or zinc(II) 2-azidomethyl-5,10,15,20-tetraphenylporphyrin with various alkyne derivatives of xanthones in DMF containing CuSO4 and ascorbic acid at 80 °C. Furthermore, these metalloporphyrins underwent demetalation under acidic conditions to afford the corresponding free-base porphyrins in good to excellent yields. After successful spectroscopic characterization, these porphyrins have been evaluated for their photophysical properties. The preliminary results revealed a bathochromic shift in the UV-vis and fluorescence spectra of these porphyrin-xanthone dyads.

SUBMITTER: Singh DK

PROVIDER: S-EPMC4578393 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Synthesis and spectroscopic properties of β-triazoloporphyrin-xanthone dyads.

Singh Dileep Kumar DK Nath Mahendra M

Beilstein journal of organic chemistry 20150817

A novel series of β-triazoloporphyrin-xanthone conjugates and xanthone-bridged β-triazoloporphyrin dyads has been synthesized in moderate to good yields through Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of copper(II) 2-azido-5,10,15,20-tetraphenylporphyrin or zinc(II) 2-azidomethyl-5,10,15,20-tetraphenylporphyrin with various alkyne derivatives of xanthones in DMF containing CuSO4 and ascorbic acid at 80 °C. Furthermore, these metalloporphyrins underwent demetalation under acidi ...[more]

PMID: 26425199

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