To Cooperate or Not: The Role of Central Functionality in Bisthiourea [6]polynorbornane Hosts

Abstract

Using fused [n]polynorbornane scaffolds functionalised at each end with a thiourea recognition unit a series of anion hosts of increasing length were constructed. The three longest [6]polynorbornyl hosts possessed central functionality to influence the binding cleft. The functional groups comprised (i) two methyl esters (ii) an unfunctionalised imide to introduce an additional N–H hydrogen‐bond donor and (iii) a large p‐anisole group to provide negative steric interactions. The family of bisthiourea hosts were evaluated for their ability to bind five aromatic dicarboxylate guests of varying shapes and lengths.