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Direct observation of structural heterogeneity and tautomerization of single hypericin molecules

  • Tautomerization is a fundamental chemical reaction which involves the relocation of a proton in the reactants. Studying the optical properties of tautomeric species is challenging because of ensemble averaging. Many molecules, such as porphines, porphycenes, or phenanthroperylene quinones, exhibit a reorientation of the transition dipole moment (TDM) during tautomerization, which can be directly observed in single-molecule experiments. Here, we study single hypericin molecules, which is a prominent phenanthroperylene quinone showing antiviral, antidepressive, and photodynamical properties. Observing abrupt flipping of the image pattern combined with time-dependent density functional theory calculations allows drawing conclusions about the coexistence of four tautomers and their conversion path. This approach allows the unambiguous assignment of a TDM orientation to a specific tautomer and enables the determination of the chemical structure in situ. Our approach can be applied to other molecules showing TDM reorientation during tautomerization, helping to gain a deeper understanding of this important process.

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Metadaten
Author of HS ReutlingenHauler, Otto; Brecht, Marc
DOI:https://doi.org/10.1021/acs.jpclett.0c03459
ISSN:1948-7185
Erschienen in:The journal of physical chemistry letters
Publisher:ACS
Place of publication:Washington, DC
Document Type:Article
Language:English
Year of Publication:2021
Volume:12
Issue:3
Page Number:7
First Page:1025
Last Page:1031
PPN:Im Katalog der Hochschule Reutlingen ansehen
DDC classes:530 Physik
Open Access?:Nein
Licence (English):License Logo  Lizenzbedingungen ACS