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001-es BibID:	BIBFORM106867
035-os BibID:	(Wos)000825749700001 (Scopus)85133129093
Első szerző:	Dékány-Adamoczky Anita (anyagmérnök)
Cím:	Isocyanonaphthol Derivatives: Excited-State Proton Transfer and Solvatochromic Properties / Anita Adamoczky, Tibor Nagy, Péter Pál Fehér, Veronika Pardi-Tóth, Ákos Kuki, Lajos Nagy, Miklos Zsuga, Sándor Kéki
Dátum:	2022
ISSN:	1422-0067
Megjegyzések:	Fluorescent probes that exhibit solvatochromic or excited-state proton-transfer (ESPT) prop- erties are essential tools for the study of complex biological or chemical systems. Herein, the synthesis and characterization of a novel fluorophore that reveals both features, 5-isocyanonaphthalene-1-ol (ICOL), are reported. Various solvatochromic methods, such as Lippert?Mataga and Bilot?Kawski, together with time-dependent density functional theory (TD-DFT) and time-resolved emission spec- troscopy (TRES), were applied to gain insights into its excited-state behavior. To make comparisons, the octyloxy derivative of ICOL, 5-isocyano-1-(octyloxy)naphthalene (ICON), was also prepared. We found that internal charge transfer (ICT) takes place between the isocyano and ?OH groups of ICOL, and we determined the values of the dipole moments for the ground and excited states of both ICOL and ICON. Furthermore, in the emission spectra of ICOL, a second band at higher wavelengths (green emission) in solvents of higher polarities (dual emission), in addition to the band present at lower wavelengths (blue emission), were observed. The extent of this dual emission increases in the order of 2-propanol < methanol < N,N-dimethylformamide (DMF) < dimethyl sulfoxide (DMSO). The presence of the dual fluorescence of ICOL in these solvents can be ascribed to ESPT. For ICOL, we also determined ground- and excited-state pKa values of 8.4 ? 0.3 and 0.9 ? 0.7, respectively, which indicates a considerable increase in acidity upon excitation. The TRES experiments showed that the excited-state lifetimes of the ICOL and ICON spanned from 10.1 ns to 5.0 ns and from 5.7 ns to 3.8 ns, respectively. In addition, we demonstrated that ICOL can be used as an effective indicator of not only the critical micelle concentration (cmc) of ionic (sodium lauryl sulfate (SLS)) and nonionic surfactants (Tween 80), but also other micellar parameters, such as partition coefficients, as well as to map the microenvironments in the cavities of biomacromolecules (e.g., BSA). It is also pointed out that fluorescence quenching by pyridine can effectively be utilized for the determination of the fractions of ICOL molecules that reside at the water?micelle interface and in the interior spaces of micelles.
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban folyóiratcikk
Megjelenés:	International Journal Of Molecular Sciences. - 23 : 13 (2022), p. 7250-7272. -
További szerzők:	Nagy Tibor (1988-) (vegyész) Fehér Péter Pál (1991-) (vegyész) Pardi-Tóth Veronika Csilla (1979-) (kémia tanár) Kuki Ákos (1966-) (villamosmérnök) Nagy Lajos (1979-) (vegyész) Zsuga Miklós (1944-) (polimer kémikus) Kéki Sándor (1964-) (polimer kémikus)
Pályázati támogatás:	K-132685 OTKA K-132236 OTKA
Internet cím:	Szerző által megadott URL DOI Intézményi repozitóriumban (DEA) tárolt változat
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