Water-soluble porphyrins with long wavelength absorption: The cyclic sulfone bridge

ORGN 792

Dabney W. Dixon, ddixon@gsu.edu and Yu Cao, ycao6@student.gsu.edu. Department of Chemistry, Georgia State University, University Plaza, Atlanta, GA 30303
Water-soluble sulfonated tetraarylporphyrins are studied in a wide variety of contexts including as analytical reagents and as possible agents in cancer photodynamic therapy as well as in antiviral and antidiabetic applications. Treatment of 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin (TPPS4) with fuming H2SO4 gave a structure consistent with initial sulfonation followed by dehydration to give a sulfone bridge between an ortho-position of one of the phenyl groups and a β-pyrrole position on the porphine ring (TPPS4Sc). The structure was established by electrospray mass spectrometry and 1H NMR. The Soret UV-visible absorption band is red shifted by about 32 nm compared to that of TPPS4. This cyclic sulfone structure also explains the spectra of sulfonated difluoroTPP derivatives, for which the spectral characteristics of members of this class are strongly dependent on the positions of the fluorine substituents. These water soluble sulfonated porphyrins with red-shifted spectra may be useful in a variety of contexts.

 

Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009