Naslov
Excited State Intramolecular Proton Transfer From Nitrogen To Carbon Atom In Aminobiphenyls

Autori
Draženović, Josip ; Rožić, Tomislav ; Došlić, Nađa ; Basarić, Nikola

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

Izvornik
27th Croatian Meeting of Chemists and Chemical Engineers and 5th Symposium Vladimir Prelog : Book of Abstracts / Marković, Dean ; Meštrović, Ernest ; Namjesnik, Danijel ; Tomašić, Vesna - Veli Lošinj : Croatian Chemical Society, 2021, 59-59

Skup
27. hrvatski skup kemičara i kemijskih inženjera i 5. Simpozij Vladimir Prelog = 27th Croatian Meeting of Chemists and Chemical Engineers and 5th Symposium Vladimir Prelog

Mjesto i datum
Veli Lošinj, Hrvatska, 05.10.2021. - 08.10.2021

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Excited State Intramolecular Proton transfer (ESPIT) ; Aminobiphenyls ; Photochemistry

Sažetak
Excited-state intramolecular proton transfer (ESIPT) is a fundamental photochemical reaction that has been intensively investigated due to numerous applications in sensing technologies and material science.[1] ESIPT takes place in molecules bearing proton donor and acceptor groups in close proximity, whose acidity and basicity are enhanced upon excitation. Furthermore, example of ESIPT between the phenolic OH and the adjacent carbon atom have been well documented. However, examples where amino functional group acts as a photoacid are scarce. Here we report on the investigation of ESIPT reactivity in o-, m- and p- aminobiphenyl derivatives. The process was investigated by irradiations in D2O-CH3CN whereupon the regiospecific deuterium incorporation took place and indirectly pointed to the ESIPT reaction mechanism. Properties of the excited states leading to the ESIPT were investigated by steady-state and time-resolved fluorescence, and we determined the pKa values of the molecules in the ground and the first singlet excited state by UV-vis and fluorescence titrations. To corroborate the experimental findings, the computations have been performed using the Algebraic Diagrammatic Construction to second order (ADC(2) method, [3] which completely unraveled the reaction mechanism and observed ESIPT photochemical pathways.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA