Tuning the Optical Properties Through Hydrogen Bond-assisted H-aggregate Formation: The ODIN Case.
H-Aggregate
electron diffraction
fluorescence
hydrogen bond
ultrafast pump-probe
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
03 Oct 2023
03 Oct 2023
Historique:
received:
10
08
2023
pubmed:
4
10
2023
medline:
4
10
2023
entrez:
3
10
2023
Statut:
aheadofprint
Résumé
The current work focuses on the investigation of two functionalized naphthyridine derivatives, namely ODIN-EtPh and ODIN-But, to gain insights into the hydrogen bond-assisted H-aggregate formation and its impact on the optical properties of ODIN molecules. By employing a combination of X-ray and electron crystallography, absorption and emission spectroscopy, time resolved fluorescence and ultrafast pump-probe spectroscopy (visible and infrared) we unravel the correlation between the structure and light-matter response, with a particular emphasis on the influence of the polarity of the surrounding environment. Our experimental results and simulations confirm that in polar and good hydrogen-bond acceptor solvents (DMSO), the formation of dimers for ODIN derivatives is strongly inhibited. The presence of a phenyl group linked to the ureidic unit favors the folding of ODIN derivatives (forming an intramolecular hydrogen bond) leading to the stabilization of a charge-transfer excited state which almost completely quenches its fluorescence emission. In solvents with a poor aptitude for forming hydrogen bonds, the formation of dimers is favored and gives rise to H aggregates, with a consequent considerable reduction in the fluorescence emission. The urea-bound phenyl group furtherly stabilizes the dimers in chloroform.
Identifiants
pubmed: 37788976
doi: 10.1002/chem.202302619
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202302619Subventions
Organisme : H2020 Marie Skłodowska-Curie Actions
ID : 101007804
Organisme : Ministero dell'Istruzione, dell'Università e della Ricerca
ID : COMP-HUB
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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