Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading
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.
Source:
RSC Advances, 2016, 6, 43, 37246-37253Publisher:
- Royal Soc Chemistry, Cambridge
Funding / projects:
DOI: 10.1039/c6ra03872g
ISSN: 2046-2069
WoS: 000374561300119
Scopus: 2-s2.0-84968807628
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IHTMTY - 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 .
Pavlovic, Radoslav Z, Bjelaković, Mira, Milić, Dragana, "Diamide-based fullerosteroidal and disteroidal [2] rotaxanes: solvent-induced macrocycle translocation and/or unthreading" in RSC Advances, 6, no. 43 (2016):37246-37253, https://doi.org/10.1039/c6ra03872g . .