title: Synthesis and preferred all-syn conformation of C3-symmetrical N-(hetero)arylmethyl triindoles.
abstract: A new series of C(3)-symmetrical N-(hetero)arylmethyl triindoles has been synthesized in a straightforward procedure. The structure and conformation in the solid state have been determined for three derivatives (3, 4, and 6) by X-ray crystallographic analysis. In all three cases, the molecules adopt a tripodal conformation with all of the flexible arms directed towards the same side, thereby delimiting an inner cavity. Compound 6 crystallizes and forms C(3)-symmetric dimeric cagelike complexes. Guest molecules of chloroform and water are confined within the resulting cavities with stabilization by different intermolecular interactions; this highlights the potential of these compounds in the construction of supramolecular systems. A computational analysis has been performed to predict the most stable conformers. As a general trend, a preference for a conformation with all branches directed to the same side has been predicted. Comparison between theoretical and experimental results indicates that the computational level selected for the present study, B3LYP/6-31G*, is able to reproduce both the minimum energy conformations and the rotation barriers about the N--CH(2) bond.
authors.affiliation: Instituto de Ciencia de Materiales de Madrid, Consejo Superior de Investigaciones Cientificas, Cantoblanco, Madrid, Spain.
authors.forename: Eva M
authors.initials: EM
authors.lastname: García-Frutos
authors.forename: Berta
authors.initials: B
authors.lastname: Gómez-Lor
authors.forename: Angeles
authors.initials: A
authors.lastname: Monge
authors.forename: Enrique
authors.initials: E
authors.lastname: Gutiérrez-Puebla
authors.forename: Ibon
authors.initials: I
authors.lastname: Alkorta
authors.forename: José
authors.initials: J
authors.lastname: Elguero