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Self-Assembly of Diboronic Esters with U‑Shaped Bipyridines: “Plug-in-Socket” Assemblies
Journal article   Open access   Peer reviewed

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 and Leonard R MacGillivray
Crystal growth & design, Vol.21(8), pp.4482-4487
08/04/2021
DOI: 10.1021/acs.cgd.1c00382
PMCID: PMC8411870
PMID: 34483748
url
https://doi.org/10.1021/acs.cgd.1c00382View
Published (Version of record) Open Access

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).
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