Self-assembly of tris(2-ureidobenzyl)amines: a new type of capped, capsule-like dimeric aggregates derived from a highly flexible skeleton |
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Authors: | Alajarín Mateo Pastor Aurelia Orenes Raúl-Angel Steed Jonathan W Arakawa Ryuichi |
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Institution: | Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, Murcia-30.100, Spain. alajarin@um.es |
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Abstract: | A set of tris(2-ureidobenzyl)amines 3 was prepared and their dimerization processes thoroughly investigated. In spite of their inherent flexibility, tris(ureas) 3 form dimeric aggregates both in the solid state and in solution. Evidence for the existence of these dimeric species was provided by a combination of techniques (X-ray analysis, NMR and IR spectroscopy, and ESI-MS). The association constants and thermodynamic parameters for the dimerization processes of selected tris(ureas) were determined and show that they are enthalpically driven. Heterodimerization experiments in solution reveal a high degree of self-recognition or narcissistic self-sorting. On the other hand, desymmetrized tris(ureas) derived from 3 self-assemble with modest regioselectivities depending on the terminal substituent of every urea functionality. |
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Keywords: | dimerization hydrogen bonds molecular recognition self‐assembly ureas |
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