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

Elif Akhuseyin Yildiz*, Yasemin Pepe, Diğdem Erdener, Ahmet Karatay, Bahadir Boyacioglu, Hüseyin Ünver, Gönül Yapar, Neslihan Demir, Mustafa Yıldız, Ayhan Elmali

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

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 hypsochromic shift by incorporating NO2 in comparison with other compounds. Femtosecond transient absorption spectroscopy measurements showed that compounds 4-hydroxy-3-(2-hydroxy-5-nitrobenzylideneamino)benzenesulfonic acid (2) and 3-(5-bromo-2-hydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (3), incorporated 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 sulfonic acid-based Schiff bases.

Original languageEnglish
Article number112048
JournalChemical Physics
Volume574
DOIs
Publication statusPublished - 1 Oct 2023

Bibliographical note

Publisher Copyright:
© 2023 Elsevier B.V.

Keywords

  • Aminobenzenesulfonic acid
  • Biological activity
  • Colorimetric sensor
  • DFT
  • Femtosecond transient absorption spectroscopy

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