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. image
2024
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]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2992135
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