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Expedient Synthesis of Oxaboracyclic Compounds Based on Naphthalene and Biphenyl Backbone and Phase‐Dependent Luminescence of their Chelate Complexes

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dc.abstract.enThe approach to a series of six- and seven-membered oxaboraheterocycles based on naphthalene or biphenyl backbones was developed. The key synthetic step involved Br/Li exchange in respective potassium (bromoaryl)trifluoroborates followed by quenching with selected electrophiles (CO2, DMF, Me2Si(H)Cl) and hydrolytic workup. Two ring-expanded benzoxaborole congeners were obtained by an additional reduction step with LiAlH4 or NaBH4. The obtained boracyclic compounds were characterized in detail by NMR spectroscopy and single-crystal X-ray diffraction. Specifically, biphenyl-based systems show dynamic behaviour interpreted in terms of inversion of non-planar seven-membered boraheterocycles. The acidity of the obtained compounds varies very strongly (pKa ranges from 3.1–9.6) depending on their structure. Due to the enhanced boron Lewis acidity, selected compounds were used as a basis for luminescent complexes with 8-hydroxyquinoline. A strong phase-dependent variation of emission-band maximum (480–527 nm) and photoluminescence quantum yield (10–95 %) was observed, which was rationalized in terms of specific aggregation effects.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorLuliński, Sergiusz
dc.contributor.authorWoźniak, Krzysztof
dc.contributor.authorDąbrowski, Marek
dc.contributor.authorGrzelak, Aleksandra
dc.contributor.authorŁaski, Piotr
dc.contributor.authorJarzembska, Katarzyna
dc.contributor.authorDrapała, Jakub
dc.contributor.authorNowicki, Krzysztof
dc.contributor.authorMarek‐Urban, Paulina H.
dc.contributor.authorDurka, Krzysztof
dc.date.accessioned2024-01-25T00:07:39Z
dc.date.available2024-01-25T00:07:39Z
dc.date.issued2022
dc.description.financeNie dotyczy
dc.description.number14
dc.description.volume28
dc.identifier.doi10.1002/CHEM.202104492
dc.identifier.issn0947-6539
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/106736
dc.identifier.weblinkhttps://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202104492
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemistry - A European Journal
dc.relation.pagese202104492
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleExpedient Synthesis of Oxaboracyclic Compounds Based on Naphthalene and Biphenyl Backbone and Phase‐Dependent Luminescence of their Chelate Complexes
dc.typeJournalArticle
dspace.entity.typePublication