The synthesis, characterization and behaviour of two novel Leigh-type amide [2]rotaxanes are reported. NMR study shows that fullerosteroidal and disteroidal rotaxanes occur in a peptide co-conformation in CDCl3. [D-6]DMSO induces fast unthreading of disteroidal rotaxane, which includes steroid co-conformers as intermediates. On the other hand, fullerosteroidal rotaxane undergoes predominantly a shuttling process occupying the stacked co-conformation, whereas unthreading is very slow in comparison with its disteroidal analogue (25% after 7 days). Moreover, organogelation and self-organization properties were studied. It was found that disteroidal rotaxane is an organogelator and its SEM image shows that it forms a branched film-like network in a PhMe/EtOAc 1 : 1 mixture.
TY - JOUR
AU - Pavlovic, Radoslav Z
AU - Bjelaković, Mira
AU - Milić, Dragana
PY - 2016
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2029
AB - The synthesis, characterization and behaviour of two novel Leigh-type amide [2]rotaxanes are reported. NMR study shows that fullerosteroidal and disteroidal rotaxanes occur in a peptide co-conformation in CDCl3. [D-6]DMSO induces fast unthreading of disteroidal rotaxane, which includes steroid co-conformers as intermediates. On the other hand, fullerosteroidal rotaxane undergoes predominantly a shuttling process occupying the stacked co-conformation, whereas unthreading is very slow in comparison with its disteroidal analogue (25% after 7 days). Moreover, organogelation and self-organization properties were studied. It was found that disteroidal rotaxane is an organogelator and its SEM image shows that it forms a branched film-like network in a PhMe/EtOAc 1 : 1 mixture.
PB - Royal Soc Chemistry, Cambridge
T2 - RSC Advances
T1 - Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading
VL - 6
IS - 43
SP - 37246
EP - 37253
DO - 10.1039/c6ra03872g
ER -
@article{
author = "Pavlovic, Radoslav Z and Bjelaković, Mira and Milić, Dragana",
year = "2016",
abstract = "The synthesis, characterization and behaviour of two novel Leigh-type amide [2]rotaxanes are reported. NMR study shows that fullerosteroidal and disteroidal rotaxanes occur in a peptide co-conformation in CDCl3. [D-6]DMSO induces fast unthreading of disteroidal rotaxane, which includes steroid co-conformers as intermediates. On the other hand, fullerosteroidal rotaxane undergoes predominantly a shuttling process occupying the stacked co-conformation, whereas unthreading is very slow in comparison with its disteroidal analogue (25% after 7 days). Moreover, organogelation and self-organization properties were studied. It was found that disteroidal rotaxane is an organogelator and its SEM image shows that it forms a branched film-like network in a PhMe/EtOAc 1 : 1 mixture.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading",
volume = "6",
number = "43",
pages = "37246-37253",
doi = "10.1039/c6ra03872g"
}
Pavlovic, R. Z., Bjelaković, M.,& Milić, D.. (2016). Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(43), 37246-37253.
https://doi.org/10.1039/c6ra03872g
Pavlovic RZ, Bjelaković M, Milić D. Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading. in RSC Advances. 2016;6(43):37246-37253.
doi:10.1039/c6ra03872g .
