Nalazite se na CroRIS probnoj okolini. Ovdje evidentirani podaci neće biti pohranjeni u Informacijskom sustavu znanosti RH. Ako je ovo greška, CroRIS produkcijskoj okolini moguće je pristupi putem poveznice www.croris.hr
izvor podataka: crosbi !

Excited State Intramolecular Proton Transfer (ESIPT) in Anthrol Carbaldehydes (CROSBI ID 650713)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija

Basarić, Nikola ; Chaiwongwattana, Sermsiri ; Došlić, Nađa ; Škalamera, Đani ; Bohne, Cornelia Excited State Intramolecular Proton Transfer (ESIPT) in Anthrol Carbaldehydes // 28th International Conference on Photochemistry / ICP 2017 / Strasbourg, Francuska. 2017. str. 54-54

Podaci o odgovornosti

Basarić, Nikola ; Chaiwongwattana, Sermsiri ; Došlić, Nađa ; Škalamera, Đani ; Bohne, Cornelia

engleski

Excited State Intramolecular Proton Transfer (ESIPT) in Anthrol Carbaldehydes

ESIPT has been intensively investigated over five decades because of its fundamental aspect in chemistry and biology, [1] as well as numerous applications in material science, [2] sensing and bioimaging.[3] The most common acidic group in ESIPT reactions is phenolic OH, [4] whereas the basic site is usually a carbonyl group.[5] Thus, among the first molecules that were experimentally found to undergo ESIPT were simple salicaldehyde derivatives. The reaction scope has later been extended to naphthol carbaldehyde derivatives.[6] However, to date, ESIPT in anthrol carbaldehydes has not been documented. Photophysical properties and reactivity in ESIPT for anthrol carbaldehydes 1-5 have been investigated computationally and experimentally by steady-state and time-resolved fluorescence and laser flash photolysis (LFP). Contrary to analogous naphthol derivatives, 1, 2-disubstituted anthrol carbaldehydes 1 and 2 are not ESIPT reactive. The main deactivation channels from S1 for 1 and 2 are fluorescence (ΦF = 0.1-0.2) and ISC to an almost isoenergetic T2 state. The triplet states from 1 and 2 were detected by LFP. On the contrary, 2, 3-disubstituted anthrols 3-5 undergo efficient barrierless ultrafast ESIPT. However, the typical dual emission from locally excited states and ESIPT tautomers were not observed since ESIPT proceeds via a conical intersection with S0 delivering keto-tautomer in the hot ground state. Therefore, anthrols 3-5 are about ten times less fluorescent, and their emission originates from less-populated conformers that cannot undergo ESIPT. Keto-tautomers for 3-5 were detected in CH3CN by LFP (λmax = 370 nm, τ = 30-40 ns). The difference in ESIPT reactivity for 1-3 was fully disclosed by calculations at ADC(2)/aug-cc-pVDZ level of theory, and particularly, by calculating the charge redistribution upon excitation to S1. Only 2, 3-disubstituted anthrols exhibit polarization in S1 that increases electron density on carbonyl and decreases on phenolic OH, setting the stage for ultrafast ESIPT.

excited state intramolecular proton transfer ; fluorescence spectroscopy, laser flash photolysis, qunatum chemical calculation

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

Podaci o prilogu

54-54.

2017.

objavljeno

Podaci o matičnoj publikaciji

28th International Conference on Photochemistry / ICP 2017 / Strasbourg, Francuska

Podaci o skupu

28th International Conference on Photochemistry / ICP 2017

poster

16.07.2017-21.07.2017

Strasbourg, Francuska

Povezanost rada

Kemija