Regiospecifically alpha-13C-labeled porphyrins for studies of ground-state hole transfer in multiporphyrin arrays

The Journal of Organic Chemistry
Ana Z MuresanDavid F Bocian

Abstract

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 (13)C atoms and the other porphyrin is unlabeled. The (13)C atoms are located at the 1- and 9-positions (alpha-carbons symmetrically disposed to the position of linker attachment), which are sites of electron/spin density in the a(1u) HOMO of the porphyrin. The (13)C labels were introduced by reaction of KS(13)CN with allyl bromide to give the allyl isothiocyanate, which upon Trofimov pyrrole synthesis followed by methylation gave 2-(methylthio)pyrrole-2-(13)C. Reaction of the latter with paraformaldehyde followed by hydrodesulfurization gave dipyrromethane-1,9-(13)C, which upon condensation with a dipyrromethane-1,9-dicarbinol bearing three pentafluorophenyl groups gave the tris(pentafluorophenyl)porphyrin bearing (13)C labels at the 1,9-positions and an unsubstituted meso (5-) position. Zinc insertion, bromination at the 5-position, and ...Continue Reading

References

Nov 15, 2000·The Journal of Organic Chemistry·P D RaoJ S Lindsey
May 10, 2003·The Journal of Organic Chemistry·Leng Leng ChngDaniel G Nocera
Jan 31, 2004·The Journal of Organic Chemistry·Shun-ichi TamaruJonathan S Lindsey
May 22, 2004·The Journal of Organic Chemistry·Patchanita ThamyongkitJonathan S Lindsey
Jun 25, 2004·Analytical and Bioanalytical Chemistry·Mario Rivera, Gregori A Caignan
Jan 28, 2006·The Journal of Organic Chemistry·Patchanita ThamyongkitJonathan S Lindsey
Jan 28, 2006·The Journal of Organic Chemistry·Patchanita ThamyongkitJonathan S Lindsey
Jun 21, 2007·The Journal of Organic Chemistry·Patchanita ThamyongkitJonathan S Lindsey
Aug 7, 2003·The Journal of Physical Chemistry. B·Nagarajan SrivatsanJames R Norris

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Citations

Oct 3, 2012·Inorganic Chemistry·Christopher J HondrosDavid F Bocian
Mar 26, 2015·Journal of Fluorescence·Gülsiye Öztürk ÜrütChandan Maity
Jan 17, 2020·ChemPlusChem·Elia MatteucciNicola Armaroli
Dec 25, 2019·Journal of the American Chemical Society·Pritam Mondal, Gayan B Wijeratne
Oct 30, 2009·Accounts of Chemical Research·Jonathan S Lindsey
May 1, 2010·The Journal of Organic Chemistry·Elías J Nieves-BernierJonathan S Lindsey
Feb 10, 2010·Organic Letters·Dilek K DogutanDaniel G Nocera
Aug 10, 2010·Journal of the American Chemical Society·James R DiersDavid F Bocian

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