{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,11]],"date-time":"2026-06-11T13:23:42Z","timestamp":1781184222129,"version":"3.54.1"},"reference-count":38,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2023,7,14]],"date-time":"2023-07-14T00:00:00Z","timestamp":1689292800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000015","name":"U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, Catalysis Science Program","doi-asserted-by":"publisher","award":["DE-SC0019094"],"award-info":[{"award-number":["DE-SC0019094"]}],"id":[{"id":"10.13039\/100000015","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The new Lewis acid\u2013base adducts of general formula X(nad)B\u2190NC5H4-C5H4N\u2192B(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\u2032-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\u2013base adduct 2d proved to be effective in forming thermally stable host\u2013guest complexes, 2d \u00d7 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\u2013guest interactions to primarily occur via \u03c0\u00b7\u00b7\u00b7\u03c0 contacts between the 4,4\u2032-bipyridyl linker and the aromatic solvents, resulting in the formation of 1:1 and 1:2 host\u2013guest complexes. Thermogravimetric analysis of the isolated complexes 2d \u00d7 solvent revealed their high thermal stability with peak temperatures associated with the loss of solvent ranging from 122 to 147 \u00b0C. 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\u2192B bonds.<\/jats:p>","DOI":"10.3390\/molecules28145394","type":"journal-article","created":{"date-parts":[[2023,7,14]],"date-time":"2023-07-14T08:40:06Z","timestamp":1689324006000},"page":"5394","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["1,8-Dihydroxy Naphthalene\u2014A New Building Block for the Self-Assembly with Boronic Acids and 4,4\u2032-Bipyridine to Stable Host\u2013Guest Complexes with Aromatic Hydrocarbons"],"prefix":"10.3390","volume":"28","author":[{"given":"Chamila P.","family":"Manankandayalage","sequence":"first","affiliation":[{"name":"Department of Chemistry & Biochemistry, Texas Tech University, P.O. Box 41061, Lubbock, TX 79409-1061, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel K.","family":"Unruh","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry, Texas Tech University, P.O. Box 41061, Lubbock, TX 79409-1061, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryan","family":"Perry","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry, Texas Tech University, P.O. Box 41061, Lubbock, TX 79409-1061, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Clemens","family":"Krempner","sequence":"additional","affiliation":[{"name":"Department of Chemistry & Biochemistry, Texas Tech University, P.O. Box 41061, Lubbock, TX 79409-1061, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,7,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2311","DOI":"10.1002\/anie.199523111","article-title":"Supramolecular synthons in crystal engineering\u2014A new organic synthesis","volume":"34","author":"Desiraju","year":"1995","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2737","DOI":"10.1021\/ja963905e","article-title":"Molecular tectonics. Porous hydrogen-bonded networks with unprecedented structural integrity","volume":"119","author":"Brunet","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1021\/ar0401799","article-title":"Molecular tectonics: From simple tectons to complex molecular networks","volume":"38","author":"Hosseini","year":"2005","journal-title":"Acc. Chem. 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