β-Functionalized Dibenzoporphyrins with Mixed Substituents Pattern: Facile Synthesis, Structural, Spectral, and Electrochemical Redox Properties
Inorganic Chemistry, 2019•ACS Publications
A new series of mixed β-substituted dibenzoporphyrins were synthesized, and the effect of β-
substitution on the spectral and electrochemical redox properties of the macrocycle was
elucidated. The synthetic route to β-tetrasubstituted dibenzoporphyrins begins with the
regioselective bromination of NiTPP (Benzo) 2 to afford NiTPP (Benzo) 2Br4, followed by Pd
catalyzed coupling reaction to access NiTPP (Benzo) 2 (R) 4 (R= phenyl (Ph) and
phenylethynyl (PE)). Synthesized benzoporphyrins exhibited red-shifted absorption spectral …
substitution on the spectral and electrochemical redox properties of the macrocycle was
elucidated. The synthetic route to β-tetrasubstituted dibenzoporphyrins begins with the
regioselective bromination of NiTPP (Benzo) 2 to afford NiTPP (Benzo) 2Br4, followed by Pd
catalyzed coupling reaction to access NiTPP (Benzo) 2 (R) 4 (R= phenyl (Ph) and
phenylethynyl (PE)). Synthesized benzoporphyrins exhibited red-shifted absorption spectral …
A new series of mixed β-substituted dibenzoporphyrins were synthesized, and the effect of β-substitution on the spectral and electrochemical redox properties of the macrocycle was elucidated. The synthetic route to β-tetrasubstituted dibenzoporphyrins begins with the regioselective bromination of NiTPP(Benzo)2 to afford NiTPP(Benzo)2Br4, followed by Pd catalyzed coupling reaction to access NiTPP(Benzo)2(R)4 (R = phenyl (Ph) and phenylethynyl (PE)). Synthesized benzoporphyrins exhibited red-shifted absorption spectral features with tunable redox properties. These benzoporphyrins displayed pronounced electronic effects of β-substituents on the macrocyclic skeleton. NiTPP(Benzo)2(PE)4 exhibited the lowest HOMO–LUMO gap among the series due to extended π-conjugation. Intrestingly, metal-centered oxidation of Ni(II)/Ni(III) was observed for NiOPP(Benzo)2 and NiOPP(Benzo)Br2 after an initial conversion of the neutral porphyrin to its dicationic form under electrochemical conditions.
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