TY - JOUR
T1 - UV-Vis spectroscopic and colorimetric anion detection and fluorescence properties of new 3-amino-4-hydroxybenzenesulfonic acid-based Schiff bases depending on the strength and position of the electron donor substitution
AU - Yildiz, Elif Akhuseyin
AU - Pepe, Yasemin
AU - Erdener, Diğdem
AU - Karatay, Ahmet
AU - Boyacioglu, Bahadir
AU - Ünver, Hüseyin
AU - Yapar, Gönül
AU - Demir, Neslihan
AU - Yıldız, Mustafa
AU - Elmali, Ayhan
N1 - Publisher Copyright:
© 2023 The Author(s). Published by IOP Publishing Ltd.
PY - 2023/8/1
Y1 - 2023/8/1
N2 - In this study, 3-amino-4-hydroxybenzenesulfonic acid-based imine compounds; 3-(2,5-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (1), 3-(2,4-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (2) and 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino)-4-hydroxybenzenesulfonic acid (3) was synthesized. The compounds were analyzed using various spectroscopy methods, and the experimental UV-vis data matched the theoretical predictions. The compound 1 displayed lower stability, higher reactivity, and easier photoexcitation due to a smaller HOMO-LUMO energy gap. The investigated compounds 1-3 showed promise as chemosensors for anions, providing visible detection in daylight conditions. The compound 3 exhibited selective fluorescence at specific wavelengths. The compounds 1-3 interacted with DNA through electrostatic interactions. Also, compounds 1-3 showed higher antioxidant activity than BHT. However, fluorescence measurements indicated that the emission signals were strongly influenced by the position and strength of the electron-donating group. Adding a hydroxy or methoxy moiety near the -OH group on the phenyl ring decreased the fluorescence signal due to intersystem crossing and intramolecular charge transfer mechanisms, respectively. These findings were supported by femtosecond transient absorption spectroscopy measurements. The results emphasize the significance of substituents in imines derived from 3-amino-4-hydroxybenzenesulfonic acid in determining their biological activities, as well as their optical and sensor properties.
AB - In this study, 3-amino-4-hydroxybenzenesulfonic acid-based imine compounds; 3-(2,5-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (1), 3-(2,4-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (2) and 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino)-4-hydroxybenzenesulfonic acid (3) was synthesized. The compounds were analyzed using various spectroscopy methods, and the experimental UV-vis data matched the theoretical predictions. The compound 1 displayed lower stability, higher reactivity, and easier photoexcitation due to a smaller HOMO-LUMO energy gap. The investigated compounds 1-3 showed promise as chemosensors for anions, providing visible detection in daylight conditions. The compound 3 exhibited selective fluorescence at specific wavelengths. The compounds 1-3 interacted with DNA through electrostatic interactions. Also, compounds 1-3 showed higher antioxidant activity than BHT. However, fluorescence measurements indicated that the emission signals were strongly influenced by the position and strength of the electron-donating group. Adding a hydroxy or methoxy moiety near the -OH group on the phenyl ring decreased the fluorescence signal due to intersystem crossing and intramolecular charge transfer mechanisms, respectively. These findings were supported by femtosecond transient absorption spectroscopy measurements. The results emphasize the significance of substituents in imines derived from 3-amino-4-hydroxybenzenesulfonic acid in determining their biological activities, as well as their optical and sensor properties.
KW - 3-amino-4-hydroxybenzenesulfonic acid
KW - anion sensor
KW - biological activity
KW - density functional theory (DFT)
KW - DPPH method
KW - femtosecond transient absorption spectroscopy
UR - http://www.scopus.com/inward/record.url?scp=85166901510&partnerID=8YFLogxK
U2 - 10.1088/1402-4896/ace806
DO - 10.1088/1402-4896/ace806
M3 - Article
AN - SCOPUS:85166901510
SN - 0031-8949
VL - 98
JO - Physica Scripta
JF - Physica Scripta
IS - 8
M1 - 085409
ER -