Colorimetric chemical sensing properties of 3-amino-4-hydroxybenzene- sulfonic acid-based Schiff bases containing electron donor-acceptor groups

Yıldız E., Pepe Y., Erdener D., Karatay A., Boyacıoğlu B., Ünver H., ...Daha Fazla

CHEMICAL PHYSICS, cilt.574, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 574
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1016/j.chemphys.2023.112048
  • Dergi Adı: CHEMICAL PHYSICS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, INSPEC
  • Anahtar Kelimeler: Aminobenzenesulfonic acid, Biological activity, Colorimetric sensor, DFT, Femtosecond transient absorption spectroscopy
  • Ankara Üniversitesi Adresli: Evet

Özet

A new series of aminobenzene sulfonic acid-based Schiff bases (1-3) were synthesized from the reaction of 3-amino-4-hydroxybenzenesulfonic acid with 5-methyl, 5-nitro and 5-bromo-salicylaldehyde. The colorimetric and UV-Vis spectroscopic responses of compounds in DMSO to addition of equivalent number of anions (F-, Br-, I-, CN-, SCN-, ClO4-, HSO4-, AcO-, H2PO4-, N3- and OH-) were investigated. Additionally, biological activities of the compounds; antimicrobial and DNA binding properties, were investigated. A DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) free radical method was used to measure antioxidant activity, and 4-hydroxy-3-(2-hydroxy-5-methylbenzylideneamino)benzene sulfonic acid (1) displayed greater antioxidant activity than butylated hydroxytoluene (BHT). Studied compounds demonstrated emission properties over a wide range of visible spectrum, and compound 4-hydroxy-3-(2-hydroxy-5-nitrobenzylideneamino)benzenesulfonic acid (2) has hyp-sochromic shift by incorporating NO2 in comparison with other compounds. Femtosecond transient absorption spectroscopy measurements showed that compounds 4-hydroxy-3-(2-hydroxy-5-nitrobenzylideneamino)benze-nesulfonic acid (2) and 3-(5-bromo-2-hydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (3), incorpo-rated nitro and bromine groups and possessing electron accepting features have fast triplet transition. This study provides a novel design strategy for biological activity and colorimetric probing features of aminobenzene sul-fonic acid-based Schiff bases.