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Supramolecular Chemistry : A Powerful Tool to create Multi-Stimuli responsive Macromolecular Assemblies

Patrice Woisel ENSCL, Lille

Interlocked structures fabricated from the electron deficient cyclophane cyclobis(paraquat-p-phenylene) (CBPQT4+)1 or cyclodextrines2 have become important building blocks for the synthesis of functional pseudorotaxanes, rotaxanes and catenanes.3 Herein, we report the successful engineering of novel “smart” polymeric systems based on well-defined polymers incorporating TTF (Tétrathiafulvalene) or naphthalene moities that have the propensity to have their self-assembly properties controlled using different external stimuli such as electrochemistry, temperature and host-guest complexation. These polymers were prepared using a RAFT procedure from new RAFT agents or monomers bearing the appropriate electron-rich units. Next, we have exploited the presence of the electron rich unit and its propensity to form pseudorotaxane type architectures with CBPQT4+ or cyclodextrine derivatives to : (i) specifically and reversibly modify, under redox4 or temperature5,6 control in organic or aqueous media, respectively, the terminus or the side chain of polymers, (ii) control the formation and the disruption of micelles7 and (iii) tune the surface wettability of gold surfaces.

1) B. Odell, M.V. Reddington, A.M.Z. Slawin, N. Spencer, J.F. Stoddart, D.J. Williams, Angew. Chem., Int. Ed. Engl.1988, 27 , 1547–1550

2) N. Tomimasu, A. Kanaya, Y. Takashima, H. Yamaguchi, A. Harada, J. Am. Chem.Soc. 2009, 6, 12339-12343.

3) A.H. Flood, Y. Liu and J.F. Stoddart In : H. Hopf and H. Gleiter, Editors, Modern Cyclophane Chemistry, Wiley-VCH, Weinheim (2004), p. 485

4) J. Bigot, M. Bria, S. T. Caldwell, F. Cazaux, A. Cooper, B. Charleux, G. Cooke, B. Fitzpatrick, D. Fournier, J. Lyskawa, M. Nutley, F. Stoffelbach, P. Woisel, Chem. Commun. 2009, 35, 5266-5268.

5) J. Bigot, B. Charleux, G. Cooke, F. Delattre, D. Fournier, J. Lyskawa, F. Stoffelbach, P. Woisel Macromolecules, 2010, 43, 82–90.

6) Bigot,J. ; Fournier, D. ; Lyskwa, J. ; Cazaux, F. ; G. Cooke,Woisel, P. Polymer Chemistry 2010, 1, 1024-1029.

7) Bigot,J. ; Charleux, B. ; Cooke, G. ; Delattre, F. ;Fournier, D. ; Lyskawa,J. ; Sambe, L. ; Stoffelbach,F. ;Woisel,P. J. Am. Chem. Soc., 2010, 132, 10796-10801