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Towards a molecular assembly based on
1,10-phenanthroline-functionalized phthalocyanines
Martynov A.G. 1,2 , Gorbunova Yu.G. 1,2 , Tsivadze A.Yu. 1,2 , Sauvage J.-P. 3
1
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS, Moscow,
Russia, martynov.alexandre@gmail.com, 2 N.S. Kurnakov Institute of General and
Inorganic Chemistry RAS, Moscow, Russia yulia@igic.ras.ru,
3
Institut de Science et d'Ingénierie Supramoléculaires, Strasbourg, France,
jpsauvage@unistra.fr
With the aim to broaden the family of molecular assemblies based on
tetrapyrrolic scaffold, we designed and synthesized a novel phthalocyanine complex,
[(MC)4Pc]Zn, bearing four lateral macrocycles containing each a phenanthroline group.
The compound turned to be almost insoluble in common organic solvents due to strong
aggregation. However, introduction of Cu(I) in the macrocycle coordination sites
afforded soluble a complex which does not aggregate in chloroform-acetonitrile mixture
as evidenced by UV-Vis spectroscopy. The attempt was made to use this complex as a
precursor to synthesize a molecular assembly with novel topological properties – two
phthalocyanine platforms held together by four linear ditopic ligands – “rails”. Bulky
“stoppers” were introduced via click-chemistry to prevent dissociation of the assembly
to individual molecular components when copper ions are removed. The target [6]rotaxane
is particularly interesting as an adaptable receptor with variable size of the
binding site located between the two phtalocyanine "plates".
Acknowledgements: This work was performed in the framework of European Research
Association “SUPRACHEM” and supported by ARCUS Alsace - Russia/Ukraine
project, RFBR (grant 09-03-93117), CNRS and the Grant of the President of Russian
Federation (МК-3595.2011.3).