On-Demand Cyclophanes: Substituent-Directed Self-Assembling, Folding, and Binding

Pierre-Thomas Skowron (1) , Bernard Dumartin (2) , Bernard Jeamet (3) , Bernard Perret (3) , Christophe Gourlaouen (4) , Anne Baudouin (5) , Bernard Fenet (5) , Jean-Valère Naubron (1) , Frédéric Fotiadu (1) , Laurent Vial (6) , Julien Leclaire (3)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
3 CSAP - Chimie Supramoléculaire Appliquée
4 Laboratoire de Chimie Quantique
5 CCRMN - Centre Commun de Résonance Magnétique Nucléaire, Université Lyon1
6 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

A family of p-cyclophanes based on bis- or tetrafunctionalized 1,4-bisthiophenol units linked by disulfide bridges was obtained by self-assembly on a gram scale and without any chromatographic purification. The nature of the functionalities borne by these so-called dyn[4]arenes plays a crucial role on their structural features as well as their molecular recognition abilities. Tuning these functions on demand yields tailored receptors for cations, anions, or zwitterions in organic or aqueous media.

Domaines: Chimie; Chimie organique; Chimie analytique; Chemo-informatique

Pierre-Thomas Skowron, Bernard Dumartin, Bernard Jeamet, Bernard Perret, Christophe Gourlaouen, et al.. On-Demand Cyclophanes: Substituent-Directed Self-Assembling, Folding, and Binding. Journal of Organic Chemistry, 2016, 81 (2), pp.654 - 661. ⟨10.1021/acs.joc.5b02605⟩. ⟨hal-01861706⟩