Oriented rotaxanes composed of tris(N-phenylureido) calix[6]arene wheel 1 and N,N′-dialkyl viologen-based axles were synthesized in which the span between the diphenylacetyl stoppers at the wheel upper and lower rim and the bispyridinium cation portion of the axial component is different in length. A sequential synthetic pathway was followed to achieve the selective formation of orientational isomers, wherein the short (or long) chain of the axle is positioned either on the upper or lower rim of the wheel. The synthetic strategy adopted involves the upper rim threading of axles 2a–c to yield oriented pseudorotaxanes, which were then stoppered in situ. The structure of the oriented rotaxanes was unravelled by detailed NMR experiments, and their spectroscopic, electrochemical and dynamic properties were investigated by UV/Vis, cyclic voltammetry, and EPR measurements. The results were compared with those of their symmetric counterparts.

Zanichelli, V., Ragazzon, G., Arduini, A., Credi, A., Franchi, P., Orlandini, G., et al. (2016). Synthesis and characterization of constitutionally isomeric oriented calix[6]arene-based rotaxanes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016(5), 1033-1042 [10.1002/ejoc.201501522].

Synthesis and characterization of constitutionally isomeric oriented calix[6]arene-based rotaxanes

RAGAZZON, GIULIO;CREDI, ALBERTO;FRANCHI, PAOLA;VENTURI, MARGHERITA;LUCARINI, MARCO;SILVI, SERENA
2016

Abstract

Oriented rotaxanes composed of tris(N-phenylureido) calix[6]arene wheel 1 and N,N′-dialkyl viologen-based axles were synthesized in which the span between the diphenylacetyl stoppers at the wheel upper and lower rim and the bispyridinium cation portion of the axial component is different in length. A sequential synthetic pathway was followed to achieve the selective formation of orientational isomers, wherein the short (or long) chain of the axle is positioned either on the upper or lower rim of the wheel. The synthetic strategy adopted involves the upper rim threading of axles 2a–c to yield oriented pseudorotaxanes, which were then stoppered in situ. The structure of the oriented rotaxanes was unravelled by detailed NMR experiments, and their spectroscopic, electrochemical and dynamic properties were investigated by UV/Vis, cyclic voltammetry, and EPR measurements. The results were compared with those of their symmetric counterparts.
2016
Zanichelli, V., Ragazzon, G., Arduini, A., Credi, A., Franchi, P., Orlandini, G., et al. (2016). Synthesis and characterization of constitutionally isomeric oriented calix[6]arene-based rotaxanes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016(5), 1033-1042 [10.1002/ejoc.201501522].
Zanichelli, V.; Ragazzon, G.; Arduini, A.; Credi, A.; Franchi, P.; Orlandini, G.; Venturi, M.; Lucarini, M.; Secchi, A.; Silvi, S.
File in questo prodotto:
Eventuali allegati, non sono esposti

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/561956
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 17
  • ???jsp.display-item.citation.isi??? 16
social impact