p-(1H-phenanthro[9,10-d]imidazol-2-yl)- substituted calix[4]arene, a deep cavity for guest inclusion |
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Authors: | Botana Enrique Nättinen Kalle Prados Pilar Rissanen Kari de Mendoza Javier |
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Institution: | Universidad Autónoma de Madrid, Departamento de Química Orgánica, Cantoblanco, 28049-Madrid, Spain. |
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Abstract: | The reaction of tetra-p-formyltetra-O-propylcalix4]arene with phenanthrenequinone in the presence of NH(4)OAc 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 pi-pi stacking interactions. |
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