Double Chalcogen Bonding Recognition Arrays in Solution

N-substituted pyridino-based congeners of Ebselen, named here as Pyrselen, incorporating proximal Se and N atoms, undergo dimerization in solution and the solid state through a dual donor-acceptor arrangement of chalcogen bonding sites. Dimerization constants were measured within the 5-50 M-1 range. Computational studies on the dimers depict a notable charge-transfer contribution to the association, validating Pyrselen as an effective scaffold for designing chalcogen-bonding-based recognition motifs.