We report on 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)] yielding discrete two-component structures. These 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 inclusion of solvent (i.e. assemblies of DPN, DAPN). The materials may form a basis for the design of complex B-based structures (e.g. supramolecular dyads).

Self-assembly of diboronic esters with u-shaped bipyridines: ‘plug-in-socket’ assemblies

ACS Spring Meeting 2021

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