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

Christopher J Hartwick; Shweta P Yelgaonkar; Eric W Reinheimer; Gonzalo Campillo-Alvarado; Leonard R MacGillivray

doi:10.1021/acs.cgd.1c00382

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

Cryst Growth Des. 2021 Aug 4;21(8):4482-4487. doi: 10.1021/acs.cgd.1c00382. Epub 2021 Jul 13.

Authors

Christopher J Hartwick¹, Shweta P Yelgaonkar¹, Eric W Reinheimer², Gonzalo Campillo-Alvarado¹, Leonard R MacGillivray¹

Affiliations

¹ Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States.
² Rigaku Oxford Diffraction, 9009 New Trails Drive, The Woodlands, Texas 77381, United States.

Abstract

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).