ChemInform Abstract: Regiospecifically α-13C-Labeled Porphyrins for Studies of Ground-State Hole Transfer in Multiporphyrin Arrays

Autor: James R. Diers, Ana Z. Muresan, Dewey Holten, David F. Bocian, Patchanita Thamyongkit, Jonathan S. Lindsey
Rok vydání: 2008
Předmět:
Zdroj: ChemInform. 39
ISSN: 1522-2667
0931-7597
DOI: 10.1002/chin.200851114
Popis: Insight into the electronic communication between the individual constituents of multicomponent molecular architectures is essential for the rational design of molecular electronic and/or photonic devices. To clock the ground-state hole/electron-transfer process in oxidized multiporphyrin architectures, a p-diphenylethyne-linked zinc porphyrin dyad was prepared wherein one porphyrin bears two 13C atoms and the other porphyrin is unlabeled. The 13C atoms are located at the 1- and 9-positions (α-carbons symmetrically disposed to the position of linker attachment), which are sites of electron/spin density in the a1u HOMO of the porphyrin. The 13C labels were introduced by reaction of KS13CN with allyl bromide to give the allyl isothiocyanate, which upon Trofimov pyrrole synthesis followed by methylation gave 2-(methylthio)pyrrole-2-13C. Reaction of the latter with paraformaldehyde followed by hydrodesulfurization gave dipyrromethane-1,9-13C, which upon condensation with a dipyrromethane-1,9-dicarbinol bearin...
Databáze: OpenAIRE
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