Synthesis of novel acylthioureas bearing naphthoquinone moiety as dual sensor for high-performance naked-eye colorimetric and fluorescence detection of CN- and F- ions and its application in water and food samples

NURAL, YAHYA; Karasu, Elize; Keles, Ergin; AYDINER, BURCU; SEFEROĞLU, NURGÜL; Efeoglu, Cagla; Şahin, Ertan; SEFEROĞLU, ZEYNEL

doi:10.1016/j.dyepig.2021.110006

Makale Tam Makale Uluslararası 2022

Synthesis of novel acylthioureas bearing naphthoquinone moiety as dual sensor for high-performance naked-eye colorimetric and fluorescence detection of CN- and F- ions and its application in water and food samples

YAHYA NURAL, Elize Karasu, Ergin Keles, BURCU AYDINER, NURGÜL SEFEROĞLU, Cagla Efeoglu, Ertan Şahin, ZEYNEL SEFEROĞLU

DYES AND PIGMENTS Cilt 198 · 01.02.2022

DOI ile aç

Özet

In this study, six new acylthiourea, bearing naphthoquinone moiety, sensors were synthesized in high yield (88-96%) and characterized using H-1/C-13 NMR, FT-IR and HRMS techniques. All synthesized sensors (4a-f) showed shifts in absorbance and colorimetric changes by CN-, F-, AcO-, and H2PO4-. However, 4e showed a chromogenic different sensitivity response to CN- and F- against competing anions such as AcO- and H2PO4- in DMSO. Furthermore, CN- added 4e showed an increase at the emission intensity and intensive fluorimetric color change was observed in UV-light (lambda ex. 365 nm). All sensors showed chromogenic selectivity towards CN- in aqueous solutions (in DMSO/H2O: 1:1, v/v). Interaction mechanisms between 4e and CN- and F- anions were investigated by experimental studies using various spectroscopic methods such as UV/Vis, fluorescence, H-1/F-19 NMR, and DFT calculation. The results showed that CN- interacts with 4e by the main mechanism as nucleophilic addition of cyanide to 3,5-dinitrophenyl moiety while F- caused an occurrence of imidazole ring-closing due to deprotonation of NH2. LOD values are reported as 2.7 mu M for sensor 4e. Moreover, interaction studies were carried out on food sample such as bitter almond, sprouting potato and apricot seed. Furthermore, UV/vis responses were obtained between sensors (4a-f) and the cations, and found selectivity towards Hg2+ in DMSO.

Anahtar kelimeler

CRYSTAL-STRUCTURE AQUEOUS-SOLUTION SELECTIVE DETECTION PROBE CHEMOSENSOR metal ions Acylthiourea / naphthoquinone dyes Hg2+ sensor CN- sensor F- sensor: Colorimetric sensors Fluorescence sensors ACID DISSOCIATION-CONSTANTS NI(II) COMPLEXES THIOUREA GROUPS FLUORIDE IONS

Atıf için künye

NURAL, Y., Karasu, E., Keles, E., AYDINER, B., SEFEROĞLU, N., Efeoglu, C., Şahin, E., & SEFEROĞLU, Z. (2022). Synthesis of novel acylthioureas bearing naphthoquinone moiety as dual sensor for high-performance naked-eye colorimetric and fluorescence detection of CN- and F- ions and its application in water and food samples. DYES AND PIGMENTS, 198. https://doi.org/10.1016/j.dyepig.2021.110006

BibTeX

@article{nural2022-66552,
  author = {NURAL, YAHYA and Karasu, Elize and Keles, Ergin and AYDINER, BURCU and SEFEROĞLU, NURGÜL and Efeoglu, Cagla and Şahin, Ertan and SEFEROĞLU, ZEYNEL},
  title = {Synthesis of novel acylthioureas bearing naphthoquinone moiety as dual sensor for high-performance naked-eye colorimetric and fluorescence detection of CN- and F- ions and its application in water and food samples},
  journal = {DYES AND PIGMENTS},
  year = {2022},
  volume = {198},
  issn = {0143-7208},
  doi = {10.1016/j.dyepig.2021.110006},
  url = {https://akademik.atauni.edu.tr/yayinlar/66552-synthesis-of-novel-acylthioureas-bearing-naphthoquinone-moiety-as-dual-sensor}
}