A novel selective fluorescent chemosensor for Fe$^{3+}$ ions based on phthalonitrile dimer:synthesis, analysis, and theoretical studies

Authors

SHAYA AL-RAQA
İPEK ÖMEROĞLU
DOĞAN ERBAHAR
MAHMUT DURMUŞ

DOI

10.3906/kim-2004-68

Abstract

Phenyl-4,4-di(3,6-dibutoxyphthalonitrile) (3) was synthesized by the reaction of 1,4-phenylenebisboronic acid (1) and 4-bromo-3,6-dibutoxyphthalonitrile (2), using Suzuki cross-coupling reaction. The newly synthesized compound (3) was characterized by FT-IR, MALDI-MS, ESI-MS, $^{1}$H-NMR, $^{13}$C-NMR, and $^{13}$C-DEPT-135-NMR. The fluorescence property of phenyl-4,4-di(3,6- dibutoxyphthalonitrile) (3) towards various metal ions was investigated by fluorescence spectroscopy, and it was observed thatthe compound (3) displayed a significantly `turn-off? response to Fe$^{3+}$, which was referred to 1:2 complex formation between ligand (3) and Fe$^{3+}$. The compound was also studied via density functional theory calculations revealing the interaction mechanism of the molecule with Fe$^{3+}$ ions.

Keywords

Phthalonitrile, Suzuki cross-coupling, fluorescence, chemosensor, Fe$^{3+}$ ion

First Page

1254

Last Page

1264

Recommended Citation

AL-RAQA, SHAYA; ÖMEROĞLU, İPEK; ERBAHAR, DOĞAN; and DURMUŞ, MAHMUT (2020) "A novel selective fluorescent chemosensor for Fe$^{3+}$ ions based on phthalonitrile dimer:synthesis, analysis, and theoretical studies," Turkish Journal of Chemistry: Vol. 44: No. 5, Article 3. https://doi.org/10.3906/kim-2004-68
Available at: https://journals.tubitak.gov.tr/chem/vol44/iss5/3