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Compound <jats:bold>1<\/jats:bold> was obtained as an equilibrium mixture of a cyclic trimer and a cyclic tetramer in solution, the latter of which was crystallized in benzene by vapor diffusion of hexane at 7\u2009\u00b0C. The dynamic nature of this system was confirmed by solvent\u2010 and concentration\u2010dependent experiments. Notably, the dynamics was verified by using flow NMR spectroscopy, which revealed that the time required to reach equilibrium was influenced by the solvent ratio (&lt;18\u2005s, 24\u201328\u2005s, and 34\u201342\u2005s in 2\u2009:\u20091, 1\u2009:\u20091, and 1\u2009:\u20092 mixtures of [D<jats:sub>6<\/jats:sub>]acetone and C<jats:sub>6<\/jats:sub>D<jats:sub>6<\/jats:sub>, respectively). Compound <jats:bold>1<\/jats:bold> and 3\u2010[4\u2032\u2010(diethylboryl)phenyl]pyridine (<jats:bold>2<\/jats:bold>) exhibited different self\u2010assembly behavior in solution and crystals. Density functional theory calculations suggested that this difference was largely due to enhanced planarity between two consecutive aromatic rings.<\/jats:p>","DOI":"10.1002\/chem.202202882","type":"journal-article","created":{"date-parts":[[2022,11,17]],"date-time":"2022-11-17T00:59:11Z","timestamp":1668646751000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Flow\u2010Chemistry\u2010Enabled Synthesis of 5\u2010Diethylboryl\u20102,3\u2032\u2010bipyridine and Its Self\u2010Assembly Dynamics"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1549-5128","authenticated-orcid":false,"given":"Shigeharu","family":"Wakabayashi","sequence":"first","affiliation":[{"name":"Department of Clinical Nutrition, Faculty of Health Science Suzuka University of Medical Science  Suzuka Mie 510-0293 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masahiro","family":"Takumi","sequence":"additional","affiliation":[{"name":"Department of Synthetic and Biological Chemistry Graduate School of Engineering Kyoto University  Nishikyo-ku Kyoto 615-8510 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shintaro","family":"Kamio","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Hokkaido University  Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masayuki","family":"Wakioka","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  Uji Kyoto 611-0011 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasuhiro","family":"Ohki","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  Uji Kyoto 611-0011 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aiichiro","family":"Nagaki","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Hokkaido University  Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,12,29]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","volume-title":"Organoboranes in Organic Synthesis","author":"Cragg M. 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