Basicity of para-substituted tetraphenylporphyrins studied by two-phase spectropotentiometric titration

Старікова, А. А.; Valiotti, A. B.; Pendin, A. A.

doi:10.1134/s1070363214010150

Cited by 2 publications

(1 citation statement)

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“…As it turned out, the order of magnitude, but also most of the pK a values, when addressed to the same porphyrin compounds, were similar to those reported elsewhere [5,10,18,37,57]. Moreover, the sequence of the pK a values collected in Table 3 appeared convergent with that of the b coefficient assigned to the porphyrin affinity for TFA ( Table 2).…”

Section: The Acid-base Equilibriumsupporting

confidence: 67%

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

et al. 2015

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Susceptibility to interact with trifluoroacetic acid (TFA) of selected freebase porphyrins, including a novel lipophilic 3-n-pentadecyl(phenoxy)-ethoxyphenyl-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 mesosubstituent and ambient medium to the reactivity and photostability of diverse porphyrin derivatives was emphasized and referred to structural features of the investigated diprotonated porphyrins.

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