Publication:
BN-Substitution in Dithienylpyrenes Prevents Excimer Formation in Solution and in the Solid State.

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dc.contributor.authorAppiarius, Yannik
dc.contributor.authorGliese, Philipp J
dc.contributor.authorSegler, Stephan A W
dc.contributor.authorRusch, Pascal
dc.contributor.authorZhang, Jiangbin
dc.contributor.authorGates, Paul J
dc.contributor.authorPal, Rumpa
dc.contributor.authorMalaspina, Lorraine
dc.contributor.authorSugimoto, Kunihisa
dc.contributor.authorNeudecker, Tim
dc.contributor.authorBigall, Nadja C
dc.contributor.authorGrabowsky, Simon
dc.contributor.authorBakulin, Artem A
dc.contributor.authorStaubitz, Anne
dc.date.accessioned2024-10-09T17:15:04Z
dc.date.available2024-10-09T17:15:04Z
dc.date.issued2022-03-10
dc.description.abstractBoron-nitrogen substitutions in polycyclic aromatic hydrocarbons (PAHs) have a strong impact on the optical properties of the molecules due to a significantly more heterogeneous electron distribution. However, besides these single-molecule properties, the observed optical properties of PAHs critically depend on the degree of intermolecular interactions such as π-π-stacking, dipolar interactions, or the formation of dimers in the excited state. Pyrene is the most prominent example showing the latter as it exhibits a broadened and strongly bathochromically shifted emission band at high concentrations in solution compared to the respective monomers. In the solid state, the impact of intermolecular interactions is even higher as it determines the crystal packing crucially. In this work, a thiophene-flanked BN-pyrene (BNP) was synthesized and compared with its all-carbon analogue (CCP) in solution and in the solid state by means of crystallography, NMR spectroscopy, UV-vis spectroscopy, and photoluminescence (PL) spectroscopy. In solution, PL spectroscopy revealed the solvent-dependent presence of excimers of CCP at high concentrations. In contrast, no excimers were found in BNP. Clear differences were also observed in the single-crystal packing motifs. While CCP revealed overlapped pyrene planes with centroid distances in the range of classical π-stacking interactions, the BNP scaffolds were displaced and significantly more spatially separated.
dc.description.numberOfPages14
dc.description.sponsorshipDepartement für Chemie, Biochemie und Pharmazie (DCBP)
dc.identifier.doi10.48350/167657
dc.identifier.pmid35299818
dc.identifier.publisherDOI10.1021/acs.jpcc.1c08812
dc.identifier.urihttps://boris-portal.unibe.ch/handle/20.500.12422/69001
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.relation.ispartofJournal of physical chemistry. C
dc.relation.issn1932-7447
dc.relation.organizationDCD5A442C14DE17DE0405C82790C4DE2
dc.subject.ddc500 - Science::570 - Life sciences; biology
dc.subject.ddc500 - Science::540 - Chemistry
dc.titleBN-Substitution in Dithienylpyrenes Prevents Excimer Formation in Solution and in the Solid State.
dc.typearticle
dspace.entity.typePublication
dspace.file.typetext
oaire.citation.endPage4576
oaire.citation.issue9
oaire.citation.startPage4563
oaire.citation.volume126
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oairecerif.author.affiliationDepartement für Chemie, Biochemie und Pharmazie (DCBP)
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oairecerif.author.affiliationDepartement für Chemie, Biochemie und Pharmazie (DCBP)
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unibe.date.licenseChanged2022-03-21 08:52:40
unibe.description.ispublishedpub
unibe.eprints.legacyId167657
unibe.journal.abbrevTitleJ PHYS CHEM C
unibe.refereedTRUE
unibe.subtype.articlejournal

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