1,8-Dihydroxy Naphthalene—A New Building Block for the Self-Assembly with Boronic Acids and 4,4′-Bipyridine to Stable Host–Guest Complexes with Aromatic Hydrocarbons

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dc.creatorManankandayalage, Chamila P. (TTU)
dc.creatorUnruh, Daniel K. (TTU)
dc.creatorPerry, Ryan (TTU)
dc.creatorKrempner, Clemens (TTU)
dc.date.accessioned2023-08-16T14:38:10Z
dc.date.available2023-08-16T14:38:10Z
dc.date.issued2023
dc.description© 2023 by the authors. cc-by
dc.description.abstractThe new Lewis acid–base adducts of general formula X(nad)B←NC5H4-C5H4N→B(nad)X [nad = 1,8-O2C10H6, X = C6H5 (2c), 3,4,5-F3-C6H2 (2d)] were synthesized in high yields via reactions of 1,8-dihydroxy naphthalene [nadH2] and 4,4′-bipyridine with the aryl boronic acids C6H5B(OH)2 and 3,4,5-F3-C6H2B(OH)2, respectively, and structurally characterized by multi-nuclear NMR spectroscopy and SCXRD. Self-assembled H-shaped Lewis acid–base adduct 2d proved to be effective in forming thermally stable host–guest complexes, 2d × solvent, with aromatic hydrocarbon solvents such as benzene, toluene, mesitylene, aniline, and m-, p-, and o-xylene. Crystallographic analysis of these solvent adducts revealed host–guest interactions to primarily occur via π···π contacts between the 4,4′-bipyridyl linker and the aromatic solvents, resulting in the formation of 1:1 and 1:2 host–guest complexes. Thermogravimetric analysis of the isolated complexes 2d × solvent revealed their high thermal stability with peak temperatures associated with the loss of solvent ranging from 122 to 147 °C. 2d, when self-assembled in an equimolar mixture of m-, p-, and o-xylene (1:1:1), preferentially binds to o-xylene. Collectively, these results demonstrate the ability of 1,8-dihydroxy naphthalene to serve as an effective building block in the selective self-assembly to supramolecular aggregates through dative covalent N→B bonds.
dc.identifier.citationManankandayalage, C.P., Unruh, D.K., Perry, R., & Krempner, C.. 2023. 1,8-Dihydroxy Naphthalene—A New Building Block for the Self-Assembly with Boronic Acids and 4,4′-Bipyridine to Stable Host–Guest Complexes with Aromatic Hydrocarbons. Molecules, 28(14). https://doi.org/10.3390/molecules28145394
dc.identifier.urihttps://doi.org/10.3390/molecules28145394
dc.identifier.urihttps://hdl.handle.net/2346/95603
dc.language.isoeng
dc.subjectaromatic hydrocarbons
dc.subjectboron
dc.subjectboronic acid
dc.subjectboronic acid ester
dc.subjectdative N→B bonding
dc.subjecthost–guest complex
dc.subjectLewis acid–base adduct
dc.subjectself-assembly
dc.subjectπ–π stacking
dc.title1,8-Dihydroxy Naphthalene—A New Building Block for the Self-Assembly with Boronic Acids and 4,4′-Bipyridine to Stable Host–Guest Complexes with Aromatic Hydrocarbons
dc.typeArticle

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