BN-Substitution in Dithienylpyrenes Prevents Excimer Formation in Solution and in the Solid State.
View / Open Files
Authors
Gliese, Philipp J
Segler, Stephan AW
Rusch, Pascal
Zhang, Jiangbin
Pal, Rumpa
Malaspina, Lorraine A
Sugimoto, Kunihisa
Publication Date
2022-03-10Journal Title
J Phys Chem C Nanomater Interfaces
ISSN
1932-7447
Publisher
American Chemical Society (ACS)
Language
eng
Type
Article
This Version
VoR
Metadata
Show full item recordCitation
Appiarius, Y., Gliese, P. J., Segler, S. A., Rusch, P., Zhang, J., Gates, P. J., Pal, R., et al. (2022). BN-Substitution in Dithienylpyrenes Prevents Excimer Formation in Solution and in the Solid State.. J Phys Chem C Nanomater Interfaces https://doi.org/10.1021/acs.jpcc.1c08812
Abstract
Boron-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.
Sponsorship
European Research Council (714429)
Identifiers
35299818, PMC8919264
External DOI: https://doi.org/10.1021/acs.jpcc.1c08812
This record's URL: https://www.repository.cam.ac.uk/handle/1810/336179
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International
Licence URL: https://creativecommons.org/licenses/by-nc-nd/4.0/
Statistics
Total file downloads (since January 2020). For more information on metrics see the
IRUS guide.
Recommended or similar items
The current recommendation prototype on the Apollo Repository will be turned off on 03 February 2023. Although the pilot has been fruitful for both parties, the service provider IKVA is focusing on horizon scanning products and so the recommender service can no longer be supported. We recognise the importance of recommender services in supporting research discovery and are evaluating offerings from other service providers. If you would like to offer feedback on this decision please contact us on: support@repository.cam.ac.uk