Research Article

Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use as Selective Cyanide Sensor

Volume: 9 Number: 2 July 30, 2026
EN

Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use as Selective Cyanide Sensor

Abstract

In this study, a coumarin based organic chemosensor bearing dicyanovinylene group has been used for the detection of CN- anion found in many living areas as environment and nature pollutant. 7-hydroxycoumarin also known as umbelliferone has been derivatized at the 3-position with dicyanovinylene group. Molecular designation of the molecule fits the donor-π-acceptor (D-π-A) systems. Here, hydroxy group at 7-position of umbelliferone is responsible for electron donation and dicyanovinylene group at 3-position is responsible for electron withdrawal. Structural characterization of the molecule has been accomplished by NMR and HRMS spectroscopic techniques. Absorption and emission spectra have been collected in the presence of various anions and the selective response in dimethylsulfoxide against CN- anion has been realized. Limit of detection (LOD) of probe molecule for CN- anions has been calculated as 1.54 μM showing that the molecule could be used as a successful cyanide probe.

Keywords

D-π-A system, Umbelliferone, Stokes shift, Selective CN- sensor

Supporting Institution

Gazi University Coordinatorship of Scientific Research Projects

Project Number

FGA-2024-9339

Ethical Statement

This study did not involve any human participants or animals. Therefore, ethics committee approval was not required.

Thanks

Author thanks to Prof. Dr. Zeynel Seferoğlu for the use of laboratory facilities.

References

  1. Aksungur, T., Aydıner, B., Seferoglu, N., Özkütük, M., Arslan, L., Reis, Y., Açık, L., Seferoglu, Z. (2017). Coumarin-indole conjugate donor-acceptor system: Synthesis, photophysical properties, anion sensing ability, theoretical and biological activity studies of two coumarin-indole based push-pull dyes. Journal of Molecular Structure, 1147, 364-379.
  2. Alkış, M., Pekyılmaz, D., Yalçın, E., Aydıner, B., Dede, Y., Seferoglu, Z. (2017). H-bond stabilization of a tautomeric coumarin-pyrazole-pyridine triad generates a PET driven, reversible and reusable fluorescent chemosensor for anion detection. Dyes and Pigments, 141, 493-500.
  3. Aydıner, B., Şahin, Ö., Çakmaz, D., Kaplan, G., Kaya, K., Özmen Özdemir, Ü., Seferoglu, N., Seferoglu, Z. (2020). A highly sensitive and selective fluorescent turn-on chemosensor bearing a 7-diethylaminocoumarin moiety for the detection of cyanide in organic and aqueous solutions. New Journal of Chemistry, 44, 19155 – 19165.
  4. Aydin, Z., Keskinates, M., Yilmaz, B., Durmaz, M., Bayrakci, M. (2022). A rapid responsive coumarin-naphthalene derivative for the detection of cyanide ions in cell culture. Analytical Biochemistry, 654, 114798 – 114794.
  5. Babür, B., Seferoglu, N., Öcal, M., Sonugur, G., Akbulut, H., Seferoglu, Z. (2016). A novel fluorescence turn-on coumarin-pyrazolone based monomethine probe for biothiol detection. Tetrahedron, 72, 4498-4502.
  6. Bouali, W., Yaman, M., Seferoglu, N., Seferoglu, Z. (2024). Colorimetric and fluorimetric detection of CN– ion using a highly selective and sensitive chemosensor derived from coumarin-hydrazone. Journal of Photochemistry & Photobiology, A: Chemistry. 448, 115227 – 115238.
  7. Cao, D., Li, Z., Verwilst, P., Koo, S., Jangjili, P., Kim, J. S., Lin, W. (2019). Coumarin-Based Small-Molecule Fluorescent Chemosensors. Chemical Reviews, 119, 10403-10519.
  8. Chen, C., Tian, R., Zeng, Y., Chu, C., Liu, G. (2020). Activatable fluorescence probes for “turn-on” and ratiometric biosensing and bioimaging: from NIR-I to NIR-II. Bioconjugate Chemistry, 31, 276–292.
  9. Cinar, S., Aktan, E., Seferoğlu, Z. (2026). Rational design and synthesis of dicyanovinylene-umbelliferone as an effective water indicator for organic solvents, RSC Advances, https://doi.org/10.1039/d6ra03978b
  10. Dai, X., Wu, Q.-H., Wang, P.-C., Tian, J., Xu, Y., Wang, S.-Q., Miao, J.-Y., Zhao, B.-X. (2014). A simple and effective coumarin-based fluorescent probe for cysteine. Biosensors and Bioelectronics, 59, 35 – 39.
APA
Çınar, S. (2026). Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use as Selective Cyanide Sensor. Journal of Apitherapy and Nature, 9(2), 192-200. https://doi.org/10.35206/jan.1965865
AMA
1.Çınar S. Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use as Selective Cyanide Sensor. J.Apit.Nat. 2026;9(2):192-200. doi:10.35206/jan.1965865
Chicago
Çınar, Seda. 2026. “Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use As Selective Cyanide Sensor”. Journal of Apitherapy and Nature 9 (2): 192-200. https://doi.org/10.35206/jan.1965865.
EndNote
Çınar S (July 1, 2026) Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use as Selective Cyanide Sensor. Journal of Apitherapy and Nature 9 2 192–200.
IEEE
[1]S. Çınar, “Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use as Selective Cyanide Sensor”, J.Apit.Nat., vol. 9, no. 2, pp. 192–200, July 2026, doi: 10.35206/jan.1965865.
ISNAD
Çınar, Seda. “Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use As Selective Cyanide Sensor”. Journal of Apitherapy and Nature 9/2 (July 1, 2026): 192-200. https://doi.org/10.35206/jan.1965865.
JAMA
1.Çınar S. Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use as Selective Cyanide Sensor. J.Apit.Nat. 2026;9:192–200.
MLA
Çınar, Seda. “Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use As Selective Cyanide Sensor”. Journal of Apitherapy and Nature, vol. 9, no. 2, July 2026, pp. 192-00, doi:10.35206/jan.1965865.
Vancouver
1.Seda Çınar. Spectroscopic Investigation of Dicyanovinylene Substituted Umbelliferone for Its Use as Selective Cyanide Sensor. J.Apit.Nat. 2026 Jul. 1;9(2):192-200. doi:10.35206/jan.1965865