meso-Aryl-substituted free-base porphyrins: formation, structure and photostability of diprotonated species

meso-Aryl-substituted free-base porphyrins: formation, structure and photostability of... Susceptibility to interact with trifluoroacetic acid (TFA) of selected free-base porphyrins, including a novel lipophilic 3-n-pentadecyl(phenoxy)-ethoxy-phenyl-substituted porphyrin, and photostability of their diprotonated compounds was explored in benzene and N,N-dimethylformamide (DMF). Results have been discussed in terms of the commonly applied pK a -based procedure and confronted with a simple approach derived from experimentally-determined correlations reflecting the porphyrins affinity for TFA. Density functional theory (DFT) has proved the porphyrin moiety creates stable diprotonated species involving two TFA molecules, in which the fluorine atoms effectively contribute to the overall interaction of the acid with the porphyrin macrocycle. The relevance of the meso-substituent and ambient medium to the reactivity and photostability of diverse porphyrin derivatives was emphasized and referred to structural features of the investigated diprotonated porphyrins. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

meso-Aryl-substituted free-base porphyrins: formation, structure and photostability of diprotonated species

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Publisher
Springer Netherlands
Copyright
Copyright © 2015 by The Author(s)
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-015-2245-5
Publisher site
See Article on Publisher Site

Abstract

Susceptibility to interact with trifluoroacetic acid (TFA) of selected free-base porphyrins, including a novel lipophilic 3-n-pentadecyl(phenoxy)-ethoxy-phenyl-substituted porphyrin, and photostability of their diprotonated compounds was explored in benzene and N,N-dimethylformamide (DMF). Results have been discussed in terms of the commonly applied pK a -based procedure and confronted with a simple approach derived from experimentally-determined correlations reflecting the porphyrins affinity for TFA. Density functional theory (DFT) has proved the porphyrin moiety creates stable diprotonated species involving two TFA molecules, in which the fluorine atoms effectively contribute to the overall interaction of the acid with the porphyrin macrocycle. The relevance of the meso-substituent and ambient medium to the reactivity and photostability of diverse porphyrin derivatives was emphasized and referred to structural features of the investigated diprotonated porphyrins.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Sep 4, 2015

References

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