Self-Assembly of Diboronic Esters with U-Shaped Bipyridines: “Plug-in-Socket” Assemblies

[Image: see text] Self-assembled complexes utilizing the ditopic dative bond acceptor 1,3-diboronic acid with catechol and complementary U-shaped donors in the form of 1,8-dipyridylnaphthalenes (1,8-bis(4-pyridyl)naphthalene (DPN), 1,8-bis(4-ethylenylpyridyl)naphthalene (DEPN), and 1,8-bis(4-ethynylpyridyl)naphthalene (DAPN)) yielded discrete two-component structures. The assemblies exhibit “plug-in-socket” geometries. DFT calculations are consistent with the donor pyridyl and acceptor catecholate being electron poor and rich, respectively. The assemblies pack via π–π interactions and support the inclusion of a solvent (i.e., DPN, DAPN). The materials may form a basis for the design of complex B-based structures (e.g., supramolecular dyads).