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Experimental and Theoretical Insights into Molecular and Solid-State Properties of Isomeric Bis(salicylaldehydes)

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dc.abstract.enA series of five bis(salicylaldehydes), including four isomeric compounds based on a benzene scaffold and a closely related naphthalene derivative, were investigated in order to elucidate the impact of resonance effects and intramolecular hydrogen bonds (HBs) on the macroscopic properties of these systems. Density functional theory (DFT) computations revealed important differences between isomers on the molecular level, which was reflected in different charge distributions, aromatic C–C bond orders, and aromaticity characters. The consequences of these features were evidenced by the UV–vis absorption spectra: for 1,3-diformyl-4,6-dihydroxybenzene (2), the longest wavelength absorption band is observed at 285 nm, while its isomers 1,4-diformyl-2,5-dihydroxybenzene (1), 1,4-diformyl-2,3-dihydroxybenzene (3), and 1,2-diformyl-3,6-dihydroxybenzene (4) are characterized by absorption in the visible range (379–407 nm). The specificity of 2 results from simultaneous lowering and elevation of HOMO and LUMO energy levels, respectively. We have found that the HOMO/LUMO energy variations follow trends observed in isomeric dihydroxybenzenes (HOMO) and phthalaldehydes (LUMO), and these effects operate separately to some extent. Furthermore, theoretical calculations indicate that the UV–vis spectral properties of bis(salicylaldehydes) are directly transferable to the corresponding bis(salicylaldimines) and their boron complexes. Finally, the influence of structural and molecular stabilization effects was analyzed by means of X-ray structural analysis and periodic DFT computations.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorDurka, Krzysztof
dc.contributor.authorGórski, Bartosz
dc.contributor.authorBłocki, Krzysztof
dc.contributor.authorLuliński, Sergiusz
dc.contributor.authorUrban, Mateusz
dc.contributor.authorBarbasiewicz, Michał
dc.contributor.authorWoźniak, Krzysztof
dc.date.accessioned2024-01-25T00:07:51Z
dc.date.available2024-01-25T00:07:51Z
dc.date.issued2019
dc.description.financeNie dotyczy
dc.description.number40
dc.description.volume123
dc.identifier.doi10.1021/ACS.JPCA.9B07360
dc.identifier.issn1089-5639
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/106749
dc.identifier.weblinkhttps://pubs.acs.org/doi/full/10.1021/acs.jpca.9b07360
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Physical Chemistry A
dc.relation.pages8674-8689
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleExperimental and Theoretical Insights into Molecular and Solid-State Properties of Isomeric Bis(salicylaldehydes)
dc.typeJournalArticle
dspace.entity.typePublication