1998
DOI: 10.1002/marc.1998.030190113
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Synthesis of mono-, oligo- and polyamide-cucurbituril rotaxanes

Abstract: SUMMARY Mono-, oligo-and polyamide rotaxanes with the macrocycle cucurbituril are synthesized easily with high yields by interfacial condensation. The complex of cucurbituril with 1,6-hexanediarnmonium ion is used as preorganized structure. With different acid and diacid chlorides a great variety of amiderotaxanes and polyrotaxanes can be synthesized. The characterization is difficult due to the low solubility of cucurbituril and rotaxanes. But with the methods of IR, DTA, 'H NMR and elemental analyses, the ex… Show more

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Cited by 25 publications
(40 citation statements)
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“…Indeed, any CB[n] complex which extends past the rim of the cavity can be considered a pseudorotaxane starting material for reactions leading to the formation of rotaxane, polyrotaxane, and polypseudorotaxanes. [186] CB [6]-based rotaxanes have been prepared in solution by dipolar cycloadditions, [147,[150][151][152]187] stoppering with dinitrophenyl groups, [188] amide-bond formation, [189][190][191][192][193] ionic interactions, [194] and coordination of alkylcobaloximes. [195,196] A variety of polymer backbones and side chains have been threaded with CB [6] beads including polyacrylamides and polystyrenes, [197] poly(hexamethyleneimine), [151,198] di-and polyviologen, [98,199] and poly(propyleneimine) dendrimers.…”
Section: Pseudorotaxanes Rotaxanes and Their Oligomeric Analoguesmentioning
confidence: 99%
“…Indeed, any CB[n] complex which extends past the rim of the cavity can be considered a pseudorotaxane starting material for reactions leading to the formation of rotaxane, polyrotaxane, and polypseudorotaxanes. [186] CB [6]-based rotaxanes have been prepared in solution by dipolar cycloadditions, [147,[150][151][152]187] stoppering with dinitrophenyl groups, [188] amide-bond formation, [189][190][191][192][193] ionic interactions, [194] and coordination of alkylcobaloximes. [195,196] A variety of polymer backbones and side chains have been threaded with CB [6] beads including polyacrylamides and polystyrenes, [197] poly(hexamethyleneimine), [151,198] di-and polyviologen, [98,199] and poly(propyleneimine) dendrimers.…”
Section: Pseudorotaxanes Rotaxanes and Their Oligomeric Analoguesmentioning
confidence: 99%
“…Thus the broad band observed for CB [7] at 3440 cm À1 is shifted to a higher frequency at 3455 cm À1 , and the characteristic carbonyl band of CB [7] at 1728 cm À1 is slightly shifted to 1733 cm À1 (broad band) due to the formation of the inclusion compound (Figure 1 a). [19,23] These frequency shifts of CB [7] indicate weak interactions (probably van der Waals forces) between the host and the guest. [19,23] A distinct IR band is noticed for the inclusion compound at 535 cm À1 , which is assigned to the n CuÀO vibration of copper acetate, in addition to the bands of CB [7]; [19] however, the corresponding band at 535 cm À1 is absent in the physical mixture and also in the spectrum of pure CB [7] ( Figure 1).…”
mentioning
confidence: 99%
“…A complex from cucurbiturile with 1,6-hexanediammoniumion serves as a pre-organized structure. Through variation of the acid chlorides it is possible to synthesize a large number of amidorotaxanes [32]. A new side chain polyrotaxane, acting as a host-guest system, enabled the dissolution of the hydrophobic acrylic acid amide derivative (guest component) using the water soluble cyclodextrine derivative (host) has been reported [33].…”
Section: Polycondensation Polyaddition Supermolecular Structuresmentioning
confidence: 99%