Plugging a bipyridinium axle into multichromophoric calix[6]arene wheels bearing naphthyl units at different rims

Orlandini, Guido ; Ragazzon, Giulio ; Zanichelli, Valeria ; Degli Esposti, Lorenzo ; Baroncini, Massimo ; Silvi, Serena ; Venturi, Margherita ; Credi, Alberto ; Secchi, Andrea ; Arduini, Arturo (2017) Plugging a bipyridinium axle into multichromophoric calix[6]arene wheels bearing naphthyl units at different rims. ChemistryOpen, 6 . pp. 64-72.
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Tris-(N-phenylureido)-calix[6]arene derivatives are heteroditopic non-symmetric molecular hosts that can form pseudorotaxane complexes with 4,4'-bipyridinium-type guests. Owing to the unique structural features and recognition properties of the calix[6]arene wheel, these systems are of interest for the design and synthesis of novel molecular devices and machines. We envisaged that the incorporation of photoactive units in the calixarene skeleton could lead to the development of systems whose working modes can be governed and monitored by means of light-activated processes. Here we report on the synthesis, structural characterization, and spectroscopic, photophysical and electrochemical investigation of two calix[6]arene wheels decorated with three naphthyl groups anchored to either the upper or lower rim of the phenylureido calixarene platform. We found that the naphthyl units interact mutually and with the calixarene skeleton in a different fashion in the two compounds, which thus exhibit a markedly distinct photophysical behavior. For both hosts, the inclusion of a 4,4'-bipyridinium guest activates energy- and/or electron-transfer processes that lead to non-trivial luminescence changes.

Document type
Orlandini, GuidoUniversità di Parma
Ragazzon, GiulioUniversità di Bologna
Zanichelli, ValeriaUniversità di Parma
Degli Esposti, LorenzoUniversità di Bologna
Baroncini, MassimoUniversità di Bologna
Silvi, SerenaUniversità di Bologna
Venturi, MargheritaUniversità di Bologna
Credi, AlbertoUniversità di Bologna
Secchi, AndreaUniversità di Parma
Arduini, ArturoUniversità di Parma
Deposit date
30 Mar 2018 10:01
Last modified
30 Mar 2018 10:01
Project name
LEAPS - Light effected autonomous molecular pumps: Towards active transporters and actuating materials
Funding program
EC - H2020

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