Synthesis of a new boron complex with imine ligand: Synthesis, characterization and fluorescent properties
Abstract
In this study, it is aimed to obtain of N,N’-Bis(3-tert-Butyl-5-methylsalicylidene)-1,2-diaminoethane-boron complex (3) in three-step reaction. In the first step, an aromatic aldehyde derivative was synthesized by the o-formylation reaction with commercially available an aromatic phenol. The condensation reaction was carried out to give the imine derivative as a Schiff base ligand (2). The fluorine chelated boron complex was synthesized through the reaction of BF3.OEt2 with ligand (2). This Schiff base-boron complex was reported for the first time and was fully characterized by common spectroscopic techniques such as 1H-NMR, 13C-NMR, FT-IR, UV–Vis, MS and elemental analysis. The spectroscopic properties of the target boron-complex were examined with the absorption and fluorescence spectroscopy. It was determined that the obtained boron complex is highly emissive molecule in different solvents with large Stokes shifts reaching 100 nm. Moreover, the measurements of the fluorescence quantum yields (up to 48%) were performed.
Keywords
References
- [1] Treibs A., Kreuzer F.H., Difluorboryl komplexe von di und tripyrrylmethenen, Justus Liebigs Ann. Chem., 718, 208-223, 1968.
- [2] Burghart A., Kim H., Welch M.B., Thoresen L. H., Reibenspies J., Burgess K., 3, 5-Diaryl-4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) dyes: synthesis, spectroscopic, electrochemical, and structural properties, J. Org. Chem., 64, 7813-7819, 1999.
- [3] Liu Y., Guo J., Zhang H., Wang Y., Highly efficient white organic electroluminescence from a double-layer device based on a boron hydroxyphenylpyridine complex, angew. Chem. Int. Ed. 41, 182-184, 2002.
- [4] Maar R.R., Barbon S.M., Sharma N., Groom H., Luyt L.G., Gilroy J.B., Evaluation of anisole-substituted boron difluoride formazanate complexes for fluorescence cell imaging, Chem. Eur. J. 21, 15589-15599, 2015.
- [5] Kowada T., Maeda H., Kikuchi K., BODIPY-based probes for the fluorescence imaging of biomolecules in living cells, Chem. Soc. Rev., 44, 4953-4972, 2015.
- [6] Kamkaew A., Lim S.H., Lee H.B., Kiew L.V., Chung L.Y., Burgess K., BODIPY dyes in photodynamic therapy, Chem. Soc. Rev., 7, 42(1), 77-88, 2013.
- [7] Moon S.Y., Cha N.R., Kim Y.H., Chang S., New Hg2+ -selective chromo- and fluoroionophore based upon 8-hydroxyquinoline. J. Org. Chem., 69, 181–183, 2004.
- [8] Hawthorne M.F., The role of chemistry in the development of boron neutron capture therapy of cancer, Angw. Chem. Iht. Ed. Engl., 32, 950-984, 1993.
Details
Primary Language
English
Subjects
Engineering
Journal Section
Research Article
Authors
Pınar Şen
*
0000-0002-3181-9890
Türkiye
Publication Date
March 16, 2019
Submission Date
June 19, 2018
Acceptance Date
February 1, 2019
Published in Issue
Year 2019 Volume: 4 Number: 1