Bis-amino maleimides: a new class of dual hydrogen bond donor for anion binding and transport

Dual hydrogen bond donor scaffolds are used in the design of numerous supramolecular receptors and play an important role in the specific recognition, reaction and transport of anionic guests. In this work, we detail the synthesis of symmetrical and unsymmetrical bis-amino maleimides as dual hydrogen bond donors and report their anion recognition and transport properties. DFT studies provide insight into the conformational preferences and binding properties of these receptors. Compared to existing dual hydrogen bond donors, the bis-amino maleimide motif contains an additional handle for synthetic functionalisation and thus offers the opportunity to tune the substituent properties to fit a desired function.