Selenoureido Calix[6]arenes: A Novel Platform for Pseudorotaxane Synthesis

Author:

Cester Bonati Federica1ORCID,Andreoni Leonardo23ORCID,Cattani Silvia1ORCID,Baccini Caterina1ORCID,Anzellotti Sara1ORCID,Cera Gianpiero1ORCID,Silvi Serena43ORCID,Secchi Andrea1ORCID

Affiliation:

1. Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale Università di Parma Parco Area delle Scienze 17/A 43124 Parma Italy

2. Dipartimento di Chimica Industriale “Toso Montanari” Università di Bologna viale del Risorgimento 4 40136 Bologna Italy

3. CLAN-Center for Light Activated Nanostructures Istituto per la Sintesi Organica e la Fotoreattività Consiglio Nazionale delle Ricerche Via Gobetti 101 40129 Bologna Italy

4. Dipartimento di Chimica “G. Ciamician” Università di Bologna Via Selmi 2 40126 Bologna Italy

Abstract

AbstractHeteroditopic 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.

Publisher

Wiley

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