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p-(1H-Phenanthro[9,10-d]imidazol-2-yl)- Substituted Calix[4]arene, a Deep Cavity for Guest Inclusion

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journal contribution
posted on 01.04.2004, 00:00 by Enrique Botana, Kalle Nättinen, Pilar Prados, Kari Rissanen, Javier de Mendoza
The reaction of tetra-p-formyltetra-O-propylcalix[4]arene with phenanthrenequinone in the presence of NH4OAc affords compound 2, a new class of calixarene with an expanded aromatic cavity, that could be stabilized by hydrogen-bonded bridges and/or ion pairing, thus preventing collapse into fully stacked pinched cone conformations as depicted. Two partially protonated calixarenes interdigitate in the solid state to give rise to a self-assembled face-to-face dimer, stabilized by π−π stacking interactions.