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Pregled bibliografske jedinice broj: 897562

Časopis

Autori: Chaiwongwattana, Sermsiri; Škalamera, Đani; Došlić, Nadja; Bohne, Cornelia; Basarić, Nikola
Naslov: Substitution Pattern on Anthrol Carbaldehydes: Excited State Intramolecular Proton Transfer (ESIPT) with a Lack of Phototautomer Fluorescence
Izvornik: PCCP. Physical chemistry chemical physics (1463-9076) 19 (2017), 41; 28439-28449
Vrsta rada: članak
Ključne riječi: Laser Flash Photolysis (LFP), Excited State Intramolecular Proton Transfer (ESIPT), anthrols, Anthrol Carbaldehydes
Sažetak:
Photophysical properties and excited state intramolecular proton transfer (ESIPT) reactivity for anthrol carbaldehydes 1-5 have been investigated computationally and experimentally by steady-state and time-resolved fluorescence and laser flash photolysis (LFP). 1, 2-Disubstituted anthrol carbaldehydes 1 and 2 are not ESIPT reactive, contrary to naphthol analogues. The main deactivation channels from S1 for 1 and 2 are fluorescence (ΦF = 0.1-0.2) and intersystem crossing (ISC) to almost isoenergetic T2 states. The triplet states from 1 and 2 were detected by LFP (in N2-purged CH3CN, τ = 15 ± 2 μs for 1, and τ = 5.5 ± 0.1 μs for 2). In contrast, 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 the keto-tautomer in the hot ground state. Therefore, anthrols 3-5 are about ten times less fluorescent compared to 1 and 2, and the emission for 3-5 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 calculation of charge redistribution upon excitation to S1. Only 2, 3-disubstituted anthrols exhibit polarization in S1 that increases the electron density on the carbonyl and decreases this density on the phenolic OH, setting the stage for ultrafast ESIPT.
Projekt / tema: HRZZ-IP-2016-06-1142, HRZZ-IP-2014-09-6312
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
MEDLINE
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL Internet adrese: http://pubs.rsc.org/en/Content/ArticleLanding/2017/CP/C7CP05472F#!divAbstract
Broj citata:
Altmetric:
DOI: 10.1039/C7CP05472F
URL cjelovitog teksta:
Google Scholar: Substitution Pattern on Anthrol Carbaldehydes: Excited State Intramolecular Proton Transfer (ESIPT) with a Lack of Phototautomer Fluorescence
Upisao u CROSBI: Enidija Lukša (Enidija.Luksa@irb.hr), 11. Lis. 2017. u 08:32 sati



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