Chinese Journal of Organic Chemistry >
Synthesis of (Pyro)pheophorbide Derivatives with Long Wavelength Absorption and Their Electronic Spectra
Received date: 2012-09-06
Revised date: 2012-09-23
Online published: 2012-10-11
Supported by
Project supported by the Technology Cooperation between Governments of China and Hungary and the Shandong Applied Research Centre of Gold Nanotechnology (2011).
Methyl pheophorbide-a and b were used as starting material. The different carbonyl groups were built along the periphery of methyl pheophorbide-a by modifing for C(3)-vinyl group, exocyclic E-ring and 20-meso-position. Making use of these carbonyl groups or original C(7)-formyl group of pheophorbide-b introduced β,β-dicyanomethylene moiety at different positions by Knoevenagel condensation with malononitrile to synthesize a series of chlorophyllous chlorin derivatives with long wavelength absorption. The effect on the electronic spectra and chemical activities of macrocycle molecule due to introduction of β,β-dicyanomethylene moiety were discussed, and the possible mechanisms about corresponding reactions were tentatively proposed. The structures of all new chlorin derivatives were characterized by 1H NMR, UV, IR spectra and elemental analysis.
Key words： chlorophyll; (pyro)pheophorbide; chlorin; synthesis; electronic spectra
Yang Ze , Wang Zhen , Liu Yang , Xu Xisen , Qi Caixia , Wang Jinjun . Synthesis of (Pyro)pheophorbide Derivatives with Long Wavelength Absorption and Their Electronic Spectra[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 116 -124 . DOI: 10.6023/cjoc201209009
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