This work focuses on the preparation and application of supramolecular structures based on mono-cinnamyl-α-cyclodextrins (Cin-α-CD). Pure regioisomers of Cin-α-CD having the cinnamyl moiety at the 2-O- or at the 3-O-position, respectively, were prepared, characterized and applied in capillary electrophoresis as additives to the background electrolyte. These new monomer units with a potential to self-organize into supramolecular structures were synthesized via a straightforward one-step synthetic procedure and purified using preparative reversed-phase chromatography allowing a large scale separation of the regioisomers. The ability of the monomers to self-assemble was proved by various methods including NMR spectroscopy and dynamic light scattering (DLS). The light scattering experiments showed that the monomer units have distinguishable ability to form supramolecular structures in different solvents and the size distribution of the aggregates in water can be easily modulated using different external stimuli, such as temperature or competitive guest molecules. The obtained results indicated that the two regioisomers of Cin-α-CD formed different supramolecular assemblies highlighting the fact that the position of the cinnamyl group plays an important role in the intermolecular complex formation.

CycloLab Cyclodextrin R and D Ltd Budapest H 1097 Illatos út 7 Hungary

Department of Analytical Chemistry Faculty of Science Charles University Prague Hlavova 8 128 43 Prague 2 Czech Republic

Department of Organic Chemistry Faculty of Science Charles University Prague Hlavova 8 128 43 Prague 2 Czech Republic

Department of Organic Chemistry Faculty of Science Charles University Prague Hlavova 8 128 43 Prague 2 Czech Republic; CycloLab Cyclodextrin R and D Ltd Budapest H 1097 Illatos út 7 Hungary

Department of Pharmacognosy Semmelweis University Budapest H 1085 Üllői út 26 Hungary

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Brunveld L, Folmer B J B, Meijer E W, Sijbesma R P. Chem Rev. 2001;101:4071–4097. doi: 10.1021/cr990125q. PubMed DOI

Bosman A W, Sijbesma R P, Meijer E W. Mater Today. 2004;7:34–39. doi: 10.1016/S1369-7021(04)00187-7. DOI

Crini G. Chem Rev. 2014;114:10940–10975. doi: 10.1021/cr500081p. PubMed DOI

Szente L, Szemán J. Anal Chem. 2013;85:8024–8030. doi: 10.1021/ac400639y. PubMed DOI

Wenz G, Han B-H, Müller A. Chem Rev. 2006;106:782–817. doi: 10.1021/cr970027+. PubMed DOI

Harada A, Takashima Y, Yamaguchi H. Chem Soc Rev. 2009;38:875–882. doi: 10.1039/b705458k. PubMed DOI

Tran N D, Colesnic D, Adam de Beaumais S, Pembouong G, Portier F, Queijo A A, Tato J V, Zhang Y, Ménand M, Bouteiller L, et al. Org Chem Front. 2014;1:703–706. doi: 10.1039/c4qo00104d. DOI

Miyauchi M, Kawaguchi Y, Harada A. J Inclusion Phenom Macrocyclic Chem. 2004;50:57–62. doi: 10.1007/s10847-004-8839-3. DOI

Tomimasu N, Kanaya A, Takashima Y, Yamaguchi H, Harada A. J Am Chem Soc. 2009;131:12339–12343. doi: 10.1021/ja903988c. PubMed DOI

Řezanka M, Jindřich J. Carbohydr Res. 2011;346:2374–2379. doi: 10.1016/j.carres.2011.08.011. PubMed DOI

Jindřich J, Tislerova I. J Org Chem. 2005;70:9054–9055. doi: 10.1021/jo051339c. PubMed DOI

Eliadou K, Giastas P, Yannakopoulou K, Mavridis M I. J Org Chem. 2003;68:8550–8557. doi: 10.1021/jo034503+. PubMed DOI

Avram L, Cohen Y. J Org Chem. 2002;67:2639–2644. doi: 10.1021/jo016321q. PubMed DOI

González-Gaitano G, Rodríguez P, Isasi J R, Fuentes M, Tardajos G, Sánchez M. J Inclusion Phenom Macrocyclic Chem. 2002;44:101–105. doi: 10.1023/A:1023065823358. DOI

Simic V, Bouteiller L, Jalabert M. J Am Chem Soc. 2003;125:13148–13154. doi: 10.1021/ja037589x. PubMed DOI

Connors K A, Rosanske T W. J Pharm Sci. 1980;69:173–179. doi: 10.1002/jps.2600690215. PubMed DOI

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin