Molecular probes and recognition processes

Keywords : Polyaromatic probes, macrocyclic and cage receptors, fluorescence signalling

We are interested in the recognition of biological targets in water (neurotransmitters, carbohydrates), using multivalent ionic receptors. Flat Triphenylene-based structures as well as fluorescent macrocycles and molecular containers are developed.

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Previous ground-breaking work from the group on the design and synthesis of photoactive supramolecular receptors for ions and neutral molecules has provided numerous examples in which binding affinity, selectivity, and photoresponse can be controlled using various inputs. [4-5] These results lay the foundations for systems exploiting substrate-induced receptor synthesis protocols, or that are capable of distinguishing between nucleobases as similar as thymine and uracil. [6] Different fundamental and applied aspects of analyte-modulated signalling pathways are being developed and employed, including photoinduced electron transfer as a means to give "off-on" fluorescence switching accompanying a molecular recognition event.[7]

We are also developing new methodologies to reversibly switch non-fluorinated compounds between aqueous/organic phases and perfluorinated phases such as perfluorocarbons. Our approach, based on coordination chemistry, exploits the reversible binding of pyridyl groups on the accessible coordination sites of highly fluorophilic copper(II)-carboxylates complexes. [8,9] We are now employing such systems in practical applications for the detection/titration of analytes such as ethanol or aqueous contaminants.

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Principle of a multiphasic colorimetric ethanol assay

Contacts :

Bassani, Dario ; Bibal, Brigitte ; Desvergne, Jean-Pierre ; McClenaghan, Nathan ; Vincent, Jean-Marc

Selected Publications :
[1] "A Fluorescent Cyclotriveratrylene : Synthesis, Emission properties and Acetylcholine recognition in water" Dumartin, M.-L. ; Givelet, C. ; Meyrand, P. ; Bibal, B. ;* Gosse, I.* Org. Biomol. Chem. 2009, 7, 2725-2728. Click Here

[2] "A hydrosoluble triphenylene that preferentially binds acetylcholine, epibatidine and nicotine" Givelet C., Buffeteau T., Arnaud-Neu F., Hubscher-Bruder V., Bibal B.,* J. Org. Chem. 2009, 74, 5059-5062. Click Here

[3] "A Simple Ionic Triphenylene Receptor for Catecholamines, Serotonin and D-Glucosamine in Buffered Water" Givelet C., Bibal B.,* Org. Biomol. Chem. 2011, 9, 7457-7460. Click Here

4 : Photochemical template-assisted synthesis of a uracil vs. thymine receptor.
D. M. Bassani, X. Sallenave, V. Darcos, J.-P. Desvergne, Chem. Commun. 2001, 1446.

5 : Synergistic effects in controlling excited-state photodimerisation using multiple supramolecular interactions.
Y. V. Pol, R. Suau, E. Perez-Inestrosa, D. M. Bassani, Chem. Commun., 2004, 1270.

6 : Detection of a single DNA base-pair mismatch using an anthracene-tagged fluorescent probe.
N. Moran, D. M. Bassani, J.-P. Desvergne, S. Keiper, P. A. S. Lowden, J. S. Vyle, J. H. R. Tucker, Chem. Commun. 2006, 5003.

7 : Switching between molecular switch types by module rearrangement
J.F. Callan, A.P. de Silva, N.D. McClenaghan, Chem. Commun. 2004, 2048.

8 : The pyridyl-tag strategy applied to the hydrocarbon/perfluorocarbon phase-switching of a porphyrin and a fullerene
M. El Bakkari, N. McClenaghan, J.-M. Vincent, J. Am. Chem. Soc. 2002, 124, 12942.

9 : Reversible fluorous phase-switching of pyridyl-tagged porphyrins : Application to the sensing of histamine in water
M. El Bakkari, B. Fronton, R. Luguya, J.-M. Vincent, J. Fluor. Chem. 12006, 127, 4-5, 558 ; (Special issue : Current Frontiers of fluoroorganic chemistry and recent advances in fluorous chemistry, Eds : D. P. Curran, K. Mikami, V. A. Soloshonok)

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