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- Title
meso-Aryl-substituted free-base porphyrins: formation, structure and photostability of diprotonated species.
- Authors
Dyrda, Gabriela; Słota, Rudolf; Broda, Małgorzata; Mele, Giuseppe
- 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-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.
- Subjects
MESO compounds; AROMATIC compounds; SUBSTITUTION reactions; PORPHYRINS; PROTON transfer reactions; CHEMICAL species; POLYMER structure
- Publication
Research on Chemical Intermediates, 2016, Vol 42, Issue 4, p3789
- ISSN
0922-6168
- Publication type
Article
- DOI
10.1007/s11164-015-2245-5