Novel Capsular Aggregates from Flexible Tripodal Triureas with Cs Symmetry

Alajarin, Mateo; Orenes, Raul-Angel; Howard, Judith A.K.; Spencer, Elinor C.; Steed, Jonathan W.; Pastor, Aurelia

Abstract

Tris(2‐ and 3‐ureidobenzyl)amines with Cs symmetry self‐assemble in solution forming mixtures of regioisomeric capsular aggregates, one of which is chiral and the other centrosymmetric. Under certain conditions, a predominance of the centrosymmetric regioisomer is found before equilibrium, that is, a mixture close to the statistical ratio of the two species is reached. In the solid state, there is a preference for the centrosymmetric capsules. Molecular models of both regioisomeric aggregates have been built and analyzed for comparison. Guests inside capsules formed by self‐assembly of desymmetrized tris(3‐ureidobenzyl)amines feel different magnetic environments, depending on whether they are inside a chiral or an achiral regioisomeric container. Of special significance are the experiments with a more flexible triurea endowed with an ureidopropylic arm, which self‐assembles with the same efficiency as the more rigid tris(ureidobenzyl)amines.

Citation

Alajarin, M., Orenes, R., Howard, J. A., Spencer, E. C., Steed, J. W., & Pastor, A. (2012). Novel Capsular Aggregates from Flexible Tripodal Triureas with Cs Symmetry. Chemistry - A European Journal, 18(8), 2389-2397. https://doi.org/10.1002/chem.201102246

• Journal Article Type: Article
• Online Publication Date: Jan 19, 2012
• Publication Date: Feb 20, 2012
• Deposit Date: Apr 1, 2021
• Publicly Available Date: Apr 7, 2021
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 18
• Issue: 8
• Pages: 2389-2397
• DOI: https://doi.org/10.1002/chem.201102246