[en] Here we present a surfactant molecule (1) containing an ammonium headgroup, in which a bis-ureido group is incorporated in its hydrocarbon chain. Due to strong hydrogen bonding interactions, 1 forms well-defined highly ordered ribbon-like aggregates in water. Moreover, we demonstrate that these ribbons can be functionalized via a modular approach through molecular recognition of other bis-urea containing molecules. The dye disperse orange and biotin were coupled to matching bis-ureido groups and incorporated into the ribbon structure. The anchoring of different functionalities in a modular approach proved to be possible using the molecular recognition capabilities of the bis-ureido moiety, thereby opening possibilities to a wide range of applications.
Disciplines :
Chemistry
Author, co-author :
Vos, M.R.J.
Etxebarria Jardi, G.
Llanes Pallas, A.
Beurken, M.
van Asselen, O.L.J.
Bomans, P.H.H.
Leclère, Philippe ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux
Frederik, P.M.
Nolte, R.J.M
Sommerdijk, N.A.J.M.
Language :
English
Title :
The Bis-Urea Motif as a Tool to Functionalize Self-Assembled Nanoribbons
Publication date :
07 December 2005
Journal title :
Journal of the American Chemical Society
ISSN :
0002-7863
Publisher :
American Chemical Society, United States - District of Columbia
Volume :
127
Issue :
48
Pages :
16768-16769
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
S817 - Chimie des matériaux nouveaux
Research institute :
R400 - Institut de Recherche en Science et Ingénierie des Matériaux
Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319.
(a) Feiters, M. C.; Nolte, R. J. M. Adv. Supramol. Chem. 2000, 6, 41-156.
(b) Shimizu, T.; Masuda, M.; Minamikawa, H. Chem. Rev. 2005, 105, 1401-1444.
(a) Kawasaki, T.; Tokuhiro, M.; Kimizuka, N.; Kunitake, T. J. Am. Chem. Soc. 2001, 123, 6792-6800.
(b) Fuhrhop, J. H.; Helfrich, W. Chem. Rev. 1993, 93, 1565-1582.
(c) Sommerdijk, N. A. J. M.; Buynsters, P. J. J. A.; Akedemir, H.; Geurts, D. G.; Pistorius, A. M. A.; Feiters, M. C.; Nolte, R. J. M.; Zwanenburg, B. Chem.-Eur. J. 1998, 4, 127-136.
(a) Hartgerink, J. D.; Beniash, E.; Stupp, S. I. Science 2001, 294, 1684-1688.
(b) Schnur, J. M. Science 1993, 262, 1669-1676.
(c) van Bommel, K. J. C.; Friggeri, A.; Shinkai, S. Angew. Chem., Int. Ed. 2003, 42, 980-999.
(d) Mann, S. J. Mater. Chem. 1995, 5, 935-946.
(e) Price, R. R.; Dressick, W. J.; Singh, A. J. Am. Chem. Soc. 2003, 125, 11259-11263.
(a) Lowik, D. W. P. M.; van Hest, J. C. M. Chem. Soc. Rev. 2004, 33, 234-245.
(b) Behanna, H. A.; Donners, J. J. J. M.; Gordon, A. C.; Stupp, S. I. J. Am. Chem. Soc. 2005, 127, 1193-1200.
(a) Wilson-Kubalek, E. M.; Brown, R. E.; Celia, H.; Milligan, R. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 8040-8045.
(b) Ringler, P.; Müller, W.; Ringsdorf, H.; Brisson, A. Chem.-Eur. J. 1997, 3, 620-625.
(a) Jung, J. H.; Yoshida, K.; Shimizu, T. Langmuir 2002, 18, 8724-8727.
(b) Archibald, D. D.; Mann, S. Nature 1993, 364, 430-433.
(a) van Esch, J.; Schoonbeek, F.; de Loos, M.; Kooijman, H.; Spek, A. L.; Kellogg, R. M.; Feringa, B. L. Chem.-Eur. J. 1999, 5, 937-950.
(b) Hanabusa, K.; Shimura, K.; Hirose, K.; Kimura, M.; Shirai, H. Chem. Lett. 1996, 885-886.
Estroff, L. A.; Hamilton, A. D. Angew. Chem., Int. Ed. 2000, 39, 3447-3450.
Moreau, J. J. E.; Pichon, B. P.; Wong Chi Man, M.; Bied, C.; Pritzkow, H.; Bantignies, J.; Dieudonn, P.; Sauvajol, J. Angew. Chem., Int. Ed. 2004, 43, 203-206.
(a) Koevoets, R. A.; Versteegen, R. M.; Kooijman, H.; Spek, A. L.; Sijbesma, R. P.; Meijer, E. W. J. Am. Chem. Soc. 2005. 127, 2999-3003.
(b) Chebotareva, N.; Bomans, P. H. H.; Frederik, P. M.; Sommerdijk, N. A. J. M.; Sijbesma, R. P. Chem. Commun. 2005, 39, 4967.
de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. E. Angew. Chem. Int. Ed. 2001, 40, 613-616.