From Self-Assembled Photoactive Architectures to Molecular Electronics

from Self-Assembled Photoactive Architectures to Molecular Electronics

Dario M. Bassani

Université Bordeaux 1

Talence, France

Supramolecular self-assembly has played a major role in the move from isolated molecules to complex, interactive ensembles, and a wide variety of well-defined supramolecular architectures have been prepared to date. In this area, our approach is characterized by the combination of photochemical and supramolecular perspectives. By combining molecular recognition units with chromophores, it is possible to use complementary molecules to bind and orient the photoactive units prior to excitation. The ensuing control of the photoinduced process is reminiscent of topochemical transformations occurring in the solid and has been demonstrated for cinnamates, stilbenes chromophore, and fullerenes. The templates serve to direct the preferential formation of specific photodimers with accrued yield and regioselectivity. By combining different recognition motifs (eg metal ion complexation and hydrogen-bonding), one can construct systems responding to multiple chemical imputs. The supramolecular structures thus prepared can themselves serve as templates for the subsequent assembly of polymeric systems, as well as for the construction of photonic devices in which the active centers are juxtaposed in a linear arrangement.

REFERENCES

(1)  N.D. McClenaghan, C. Abselon, D. M. Bassani; “Facile Synthesis of a Fullerene-Barbituric Acid Derivative and Supramolecular Catalysis of Its Photoinduced Dimerization” J. Am. Chem. Soc. 2003, 125, 13004 – 13005.

(2)  Y. Molard, D. M. Bassani, J.-P. Desvergne, P. N. Horton, M. B. Hursthouse, J. H. R. Tucker "Photorelease of an Organic Molecule in Solution: Light-triggered Blockage of a Hydrogen-bonding Receptor Site" Angew. Chemie, Int. Ed. 2005, 44, 2 - 5.

(3)  Y. V. Pol, R. Suau, E. Perez-Inestrosa, D. M. Bassani "Synergistic effects in controlling excited-state photodimerisation using multiple supramolecular interactions" Chem. Commun. 2004, 1270 – 1271.

(4)  N. D. McClenaghan, Z. Grote, K. Darriet, M. Zimine, R. M. Williams, L. De Cola, D. M. Bassani Org. Lett. 2005, 7, 807 – 810.

(5)  R. Baron, C.-H. Huang, D. M. Bassani, A. Onopriyenko, M. Zayats, I. Willner "H-Bonded CdS Nanoparticle Assemblies on Electrodes for Photoelectrochemical Applications" Angew. Chemie, Int. Ed. 2005, , 44, 4010.

(6)  Chih-Hao Huang, Nathan D. McClenaghan, Alexander Kuhn, Georges Bravic, Dario M. Bassani. "Hierarchical self-assembly of all-organic photovoltaic devices", Tetrahedron (Special issue on fullerenes) 2006, 62, 2050 - 2059.

(7)  Cheng-Che-Chu, Dario M. Bassani. "Challenges and Opportunities for Photochemists on the Verge of Solar Energy Conversion", Photochem. Photobiol Sci. 2008, 7, 521 – 530.

Dario Bassani was born in Milan, Italy, and after obtaining a Licence en Chimie degree from the Université Catholique de Louvain (Belgium), completed a doctoral degree in the field of organic photochemistry in 1993 under the guidance of Professor F. D. Lewis at Northwestern University (USA). He then undertook a postdoctoral position as a Hoffmann-La Roche fellow with Professor J. Wirz (Basel University, Switzerland), followed by a second postdoctoral position as a Marie Curie Fellow with Professor J.-M. Lehn in Strasbourg (France). He joined the Centre National de la Recherche Scientifique in 1997 as research scientist appointed to the Institut des Sciences Moléculaires (CNRS UMR 5255) at Bordeaux University, where he conducts research bridging photochemistry and supramolecular chemistry. He serves on the editorial board for Photochem. Photobiol. Sci. and is the recipient of the Inter-American Photochemical Society Young Investigator Award (2003), the French Chemical Society Award (Physical Chemistry Division, 2004) and the Grammaticakis-Neuman Prize of the Swiss Chemical Society (2005).