Heteroditopic calix[6]arenes are widely employed macrocycles for the synthesis of pseudo-oriented interlocked systems and stimuli-induced molecular machines, among others. Herein, we introduce a new calix[6]arene receptor functionalised with three phenylselenoureido groups. These hydrogen-bonding donor moieties are able to promote the threading of viologen-based organic axles inside the macrocyclic cavity to form a stable pseudorotaxane species. Preliminary investigations using 1H-NMR measurements and semi-empirical and DFT studies suggested its further use as a platform for the synthesis of rotaxanes.We described the synthesis and characterisation of a heteroditopic calix[6]arene receptor functionalised with three phenyl selenoureido groups at the upper rim of the macrocycle. A detailed investigation using NMR, DFT, UV-Vis and cyclic voltammetry suggested its use as a novel platform for pseudorotaxane synthesis. image
Selenoureido Calix[6]arenes: A Novel Platform for Pseudorotaxane Synthesis / Cester Bonati, F.; Andreoni, L.; Cattani, S.; Baccini, C.; Anzellotti, S.; Cera, G.; Silvi, S.; Secchi, A.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 27:27(2024). [10.1002/ejoc.202400237]
Selenoureido Calix[6]arenes: A Novel Platform for Pseudorotaxane Synthesis
Cester Bonati F.Investigation
;Cattani S.Investigation
;Baccini C.Investigation
;Anzellotti S.Investigation
;Cera G.
;Secchi A.
2024-01-01
Abstract
Heteroditopic calix[6]arenes are widely employed macrocycles for the synthesis of pseudo-oriented interlocked systems and stimuli-induced molecular machines, among others. Herein, we introduce a new calix[6]arene receptor functionalised with three phenylselenoureido groups. These hydrogen-bonding donor moieties are able to promote the threading of viologen-based organic axles inside the macrocyclic cavity to form a stable pseudorotaxane species. Preliminary investigations using 1H-NMR measurements and semi-empirical and DFT studies suggested its further use as a platform for the synthesis of rotaxanes.We described the synthesis and characterisation of a heteroditopic calix[6]arene receptor functionalised with three phenyl selenoureido groups at the upper rim of the macrocycle. A detailed investigation using NMR, DFT, UV-Vis and cyclic voltammetry suggested its use as a novel platform for pseudorotaxane synthesis. imageI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.