Repozytorium
Wyszukaj
Kolekcje
Inne
Theoretical Insights into the Impact of Pyrrole and Imidazole Substituents on the BODIPY Chromophore
Autorzy
Rok wydania
2025
Czasopismo
Numer woluminu
30
Strony
2209/1-2209/14
DOI
10.3390/molecules30102209
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
This paper concerns the in silico studies of the influence of heterocyclic substituents as well as their protonated and deprotonated forms on the spectral characteristics of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) dyes. Computational studies were carried out in order to reveal the most effective method of modeling of the spectral features of fluorescent BODIPY dyes. To perform these studies, the pyrrole and imidazole derivatives of BODIPY dyes were selected, and their spectral features were investigated with DFT and TD-DFT calculations. The calculations showed that the deprotonation of the substituents leads to a bathochromic shift of the calculated absorption wavelength, while the protonation (imidazole derivative) brings about a hypsochromic shift with respect to the neutral form of the dye. The calculated spectral characteristics, considering the influence of the solvent polarity (PCM model), were correlated with the ENTETN solvatochromic parameter. These correlations show that the increase in the solvent polarity causes a hypsochromic shift of the calculated absorption and emission wavelengths, whereas the bathochromic shift of the wavelengths is observed for the protonated form.
Słowa kluczowe
BODIPY dye, protonation, deprotonation, DFT, TD-DFT
Licencja otwartego dostępu
Licencja na prawach której można swobodnie kopiować, rozprowadzać, zmieniać i remiksować objęty prawem autorskim utwór (Utwór-przedmiot prawa autorskiego) pod warunkiem podania imienia i nazwiska autora utworu pierwotnego oraz źródła pochodzenia utworu.
Pełny tekst licencji: https://creativecommons.org/licenses/by/3.0/pl/legalcode
Adres publiczny
http://dx.doi.org/10.3390/molecules30102209
Strona internetowa wydawcy
Podobne publikacje
The photoinactivation of pathogenic bacteria using synthesized benzodioxole-BODIPY dyes
Tursynova Nurgul, Maliszewska Irena Helena, Jóźwiak Kinga, Sokolnicki Jerzy, Kochel Andrzej, Lipkowski Paweł, Bartkiewicz Stanisław, Filarowski Aleksander
Calculations of BODIPY dyes in the ground and excited states using the M06-2X and PBE0 functionals.
Laine Marina, Barbosa Nuno A., Wieczorek Robert, Melnikov Mikhail Ya., Filarowski Aleksander
Synthesis, structural, spectroscopic, computational and cytotoxic studies of BODIPY dyes.
Laine Marina, Barbosa Nuno A., Kochel Andrzej, Osiecka B. J., Szewczyk G., Sarna T., Ziółkowski Piotr, Wieczorek Robert, Filarowski Aleksander