Naslov
Spectroscopic and computational study of novel pH sensitive probes based on benzo[b]thienopyridil- benzimidazoles

Autori
Vianello, Robert ; Babić, Darko ; Perin, Nataša ; Hranjec, Marijana

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
7th EuCheMS Chemistry Congress: Molecular frontiers & global challenges / - Liverpool, 2018

Skup
7th EuCheMS Chemistry Congress

Mjesto i datum
Liverpool, Ujedinjeno Kraljevstvo, 26.08.2018. - 30.08.2018

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
pH sensitive probes ; benzimidazole fragment ; computational study

Sažetak
We describe the UV-Vis and fluorescence spectroscopic characterization of three new amino substituted benzo[b]thieno[2, 3-b]pyrido[1, 2- a]benzimidazoles 1–3 in order to evaluate their photophysical features and assess their potential chemosensor activity as pH sensors. The general structure of these systems is based on a fused and highly conjugated planar chromophore system that leads to excellent optical properties such as strong fluorescence in the visible spectrum and good photostability. Inspection of the changes in their spectroscopic parameters depending on the pH value revealed that the protonation/deprotonation equilibria of the dyes is accompanied with drastic changes in photophysical properties. For example, the fluorescence intensity of 3 strongly increases upon the exposure to acidic conditions. Computational analysis elucidated the correct protonation forms responsible for the observed spectroscopic trends and showed that the corresponding acid/base changes occur in the range pH = 3–5, in accordance with experiments. It also enabled a consistent interpretation of the measured UV/Vis and fluorescence spectra. In view of their analytical applicability, and based on the agreement between computational and experimental data, we propose two additional promising systems (4 and 5) with improved acid/base (pKa = 7–9) and spectroscopic features, and their synthesis is highly recommended.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA