ORGANIC
LETTERS
2011
Vol. 13, No. 17
4742–4745
Diporphyrinylamines: Synthesis and
Electrochemistry
†
†
Ana M. V. M. Pereira,†,‡ Maria G. P. M. S. Neves, Jose A. S. Cavaleiro,
Christophe Jeandon,‡ Jean-Paul Gisselbrecht,‡ Sylvie Choua,‡ and
Romain Ruppert*,‡
ꢀ
Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro,
ꢀ
Portugal, and Institut de Chimie, UMR 7177 du CNRS, Universite de Strasbourg,
1 rue Blaise Pascal, 67000 Strasbourg, France
Received July 29, 2011
ABSTRACT
The synthesis of three possible diporphyrinylamines is described. All compounds were obtained by using the BuchwaldꢀHartwig aromatic
amination reaction. The electronic spectra of the three porphyrin dimers showed characteristic features found in highly delocalized systems. The
first oxidation of these compounds took place on the connecting amine function.
Highly π-extended molecules, or molecules in which
electron delocalization is found over a large space or
length, are still the subject of numerous studies because
these compounds might lead to new molecular materials.1
In the particular case of porphyrin chemistry, covalent
conjugated connections have been intensively studied lead-
ing to species with improved electronic properties.2 More
recently, coordination bonds were used as connectors, and
similar electron delocalization over two or several por-
phyrins linked by metal ions was reported.3
A few years ago, Arnold et al. prepared the dipor-
phyrinylamine 1, in which the amino function cova-
lently linked the meso positions of the two porphyrinic
units.4 Although the connecting bonds were exclusively
† University of Aveiro.
(4) Esdaile, L. J.; Senge, M. O.; Arnold, D. P. Chem. Commun. 2006,
4192.
‡
ꢀ
Universite de Strasbourg.
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r
10.1021/ol2020658
Published on Web 08/11/2011
2011 American Chemical Society