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• W2084158850 endingPage "10483" @default.
• W2084158850 startingPage "10474" @default.
• W2084158850 abstract "A homologous set of porphyrin derivatives possessing an isocyclic five-membered ring appended with an amidinium functionality has been used to examine proton-coupled electron transfer (PCET) through well-characterized amidine−carboxylic acid interfaces. Conjugation between the porphyrin chromophore and the amidinium interface can be altered by selective reduction of the isocyclic ring of an amidinium−purpurin to produce an amidinium−chlorin. The highly conjugated amidinium−purpurin displays large spectral shifts in the visible region upon alteration of the amidinium/amidine protonation state; no such change is observed for the chlorin homologue. Analysis of the UV−vis absorption and emission profiles of the amidinium−purpurin upon deprotonation allows for the measurement of the porphyrinic-amidinium acidity constant for the ground state (pKa = 9.55 ± 0.1 in CH3CN) and excited state (pKa* = 10.40 ± 0.1 in CH3CN). The absorption spectrum of the purpurin also provides a convenient handle for determining the protonation state of assembled interfaces. In this way, the purpurin macrocycle provides a general tool for PCET studies because it can be used to determine the location of a proton within PCET interfaces formed from carboxylic acid electron acceptors including dinitrobenzenes (DNBs) and naphthalenediimide (NI), which have been used extensively in previous PCET studies. An amidine−carboxylic acid interface is observed for electron-rich acceptors, whereas the ionized amidinium−carboxylate interface is observed for electron-poor acceptors. The PCET kinetics for purpurin/chlorin associated to NI are consistent with an amidine−carboxylic acid interface, which is also verified spectrally." @default.
• W2084158850 created "2016-06-24" @default.
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• W2084158850 date "2006-07-26" @default.
• W2084158850 modified "2023-10-17" @default.
• W2084158850 title "Spectroscopic Determination of Proton Position in the Proton-Coupled Electron Transfer Pathways of Donor−Acceptor Supramolecule Assemblies" @default.
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• W2084158850 doi "https://doi.org/10.1021/ja062430g" @default.
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