Calix 2015 – 13th International Conference on Calixarenes – Giardini Naxos (Italy) 5-9 July 2015
Nitrobenzylbambusurils
K. Tomasikova,a
M. A. Yawer,a
L. Pavlovec,a
and V. Sindelara
a
Department of Chemistry and Research Centre for Toxic Compounds in the Environment,
Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic.
E-mail: 177422@mail.muni.cz
Glycoluril is a bicyclic molecule used as building block in two classes of synthetic macrocyclic
receptors called cucurbiturils1
and bambusurils2
.Cucurbiturils are known for their molecular
recognition of cations, whereas bambusurils are valuable for the strong complexation of anions.
At this conference, we will present a selective preparation leading to the new type of
bambusurils, namely nitrobenzylbambusurils. Nitrobenzylbambusurils are macrocycles formed
by 2,4-disubstituted glycoluril units linked with methylene bridges. This structural feature
determines bambusurils for the complexation of anions due to hydrogen bonding between
methine hydrogen atoms of the macrocycle and encapsulated anion. Depending on the reaction
conditions we are able to isolate nitrobenzylbambusurils with different sizes. The potential use
of nitrobenzylbambusuril is not only in the complexation of anions, but also in the further
modification of nitrobenzyl-groups giving us broader extension of bambusuril family.
Figure 1. Substituted bambusuril, R = nitrobenzyl group.
Acknowledgments
Support for this work was provided by the Czech Science Foundation (13-15576S) and the
Czech Ministry of Education (projects LM2011028 and LO1214).
1
Lagona, J.; Mukhopadhyay, P.; Chakrabarti; S.; Isaacs, L. Angew. Chem. Int. Ed. 2005, 44, 4844–4870.
2
Havel, V.; Svec J.; Wimmerova, M.; Dusek, M; Pojarova, M; Sindelar, V. Org. Lett. 2011, 13, 4000–
4003.