Self-assembled molecular networks

 

Nature uses weak non-covalent interactions to build complex biomolecules and whole organisms through a process of self-assembly. We would like to employ such self-assembly properties of organic matter for bottom-up construction of complex (opto)electronic devices based on organic semiconducting molecules.

We design and synthesize (hetero)aromatic molecules with weakly binding functionalities (hydrogen bonding, halogen bonding, etc) which can be used as "nanoscopic bricks" to build a nanopattern of a given symmetry and periodicity. In collaboration with the group of Prof. Rosei (INRS), we use scanning tunneling microscopy (STM) to directly observe how molecular associations are formed and transformed in real time, both in Ultra-High Vacuum (at INRS) and at solid-liquid interface (at McGill and INRS). Density Functional Calculations are actively employed to interpret the STM images and to understand the molecular interactions in such systems.

Figure below shows the STM studies of host-guest self-assembly of terthienobenzenetricarboxylic acid with C60 fullerene, as a model "bulk heterojunction" system for organic photovoltaics (solar cells).

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Published papers:

Mastering Fundamentals of the Supramolecular Design with Carboxylic acids. Common lessons from X-ray cryslallography and scanning tunneling microscopy,
O. Ivasenko, D.F. Perepichka*, Chem. Soc. Rev. 2011, 40, 191-206.

Supramolecular ordering in oligothiophene-filerene monolayers studied by STM,
J.M. MacLeod, O. Ivasenko, C. Fu, T. Taerum, F. Rosei*, D.F. Perepichka*, J.Am. Chem. Soc. 2009, 131, 16844-16850.

Supramolecular assembly of heterocirculenes in 2D and 3D,
O. Ivasenko, J. M. MacLeod, K. Yu. Chernichenko, E. Balenkova, R. V. Shpachenko, V. G. Nenajdenko, F. Rosei, D. F. Perepichka, Chem. Commun., 2009, 1192-1194.

Molecular assembly of rubrene on a metal/metal oxide nanotemplate,
F. Cicoira, J. A. Miwa, D. F. Perepichka, F. Rosei, J. Phys. Chem. A 2007, 111, 12674-12678.

Crystal engineering in two dimensions: an approach to molecular nanopatterning,
K.G. Nath, O. Ivasenko, J.L. Macleod, J.A. Miwa, J.D. Wuest, A. Nanci, D.F. Perepichka, F. Rosei, J. Phys. Chem. C 2007, 111, 16996-1700.

Stabilization of exotic minority phases in a multicomponent self-assembled molecular network,
J. M. Macleod, O. Ivasenko, D. F. Perepichka, F. Rosei, Nanotechnology 2007, 18, 424031.

Rational Modulation of the Periodicity in Linear Hydrogen-Bonded Assemblies of Trimesic Acid on Surfaces,
K. Nath, O. Ivasenko, J. A. Miwa, H. Dang, J. D. Wuest, A. Nanci, D. F. Perepichka, F. Rosei, J. Am. Chem. Soc. 2006, 128, 4212-4213.

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