Haas Marco, Liu Shi-Xia, Kahnt Axel, Leiggener Claudia, Guldi Dirk M, Hauser Andreas, Decurtins Silvio
Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern, Switzerland.
J Org Chem. 2007 Sep 28;72(20):7533-43. doi: 10.1021/jo0710477. Epub 2007 Sep 7.
An unsymmetric, peripherally octasubstituted phthalocyanine (Pc) 1, which contains a combination of dipyrido[3,2-f:2',3'-h] quinoxaline and 3,5-di-tert-butylphenoxy substituents, has been obtained via a statistical condensation reaction of two corresponding phthalonitriles. Synthetic procedures for the selective metalation of the macrocyclic cavity and the periphery of 1 were developed, leading to the preparation of the key precursor metallophthalocyanines 3-5 in good yields. Two different strategies were applied to the synthesis of compact dyads MPc-Ru(II) 6-8 (M = Mg(II), Co(II), Zn(II)). Intramolecular electronic interactions in these dyads were studied by absorption, emission, and transient absorption spectroscopy. Upon photoexcitation, these dyads exhibit efficient intramolecular energy transfer from the Ru(II) chromophore to the MPc moiety.
