Synthesis of a new boron complex with imine ligand: Synthesis, characterization and fluorescent properties

Year 2019, , 46 - 52, 16.03.2019

Pınar Şen

https://doi.org/10.30728/boron.434776

Cited By: 1

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

Fluorine boron complex, fluorescence property, Schiff base ligand, Synthesis, Red-shift emission, Stokes’ shift, quantum yield.

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.
• [9] Qiao F., Liu A., Zhou Y., Xiao Y., Yang P.O., Bulk heterojunction organic solar cell based on a novel fluorescent fluorine–boron complex, J. Mater. Sci., 44, 1283-1286, 2009.
• [10] Tamgho I., Hasheminasa A., Engle J.T., Nemykin V.N., Ziegler C.J., A new highly fluorescent and symmetric pyrrole-BF2 chromophore: BOPHY, J. Am. Chem. Soc., 136, 5623−5626, 2014.
• [11] Yu C., Zhang L.J.P., Feng Z., Cheng C., Wei Y., Mu X., Hao E., Highly fluorescent BF2 complexes of hydrazine–schiff base linked bispyrrole, Org. Lett., 16, 3048-3051, 2014.
• [12] Zhang H., Huo C., Zhang J., Zhang P., Tian W., Wang Y., Efficient single-layer electroluminescent device based on a bipolar emitting boron-containing material, Chem. Commun., 3, 281-283, 2006.
• [13] Guieu S., Cardona F., Rochab J., Silva A.M.S., Luminescent bi-metallic fluoroborates derivatives of bulky Salen ligands, New. J. Chem., 38, 5411-5414, 2014.
• [14] Perrin D.D., Armarego W.L.F., Perrin D.R. Purification of laboratory chemicals, New York: Pergamon Press, 2013.
• [15] Larrow J.F., Jacobsen E.N., A practical method for the large-scale preparation of [N,N'-Bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]manganese(III) chloride, a highly enantioselective epoxidation catalyst, J. Org. Chem., 59, 1939-1942, 1994.
• [16] Sen P., Kansiz S., Golenyac I.A., Dege N., Crystal structure and Hirshfeld surface analysis of N,N’-bis(3-tert-butyl-2-hydroxy-5-methylbenzylidene) ethane-1,2-diamine, Acta Cryst. E74, 1147-1150, 2018.
• [17] Kilic A., Kayan C., Aydemir M., Durap F., Durgun M., Baysal A., Tas E., Gumgum B., Synthesis of new boron complexes: Application to transfer hydrogenation of acetophenone derivatives, Appl. Organometal. Chem., 25, 390-394, 2011.
• [18] Lever A.B.P., Inorganic Electronic Spectroscopy, second ed., Elsevier Science, Amsterdam, 1984.
• [19] Frath D., Azizi S., Ulrich G., Retailleau P., Ziessel R., Facile synthesis of highly fluorescent boranil complexes, Org. Lett., 13, 3414-3417, 2011.
• [20] Ren Yi., Liu X., Gao W., Xia H., Ye L., Mu Y., Boron complexes with chelating anilido-imine ligands: Synthesis, structures and luminescent properties, Eur. J. Inorg. Chem., 2007, 1808–1814, 2007.
• [21] Peng X., Song F., Lu E., Wang Y., Zhou W., Fan J., Gao Y., Heptamethine Cyanine Dyes with a Large Stokes Shift and Strong Fluorescence: A Paradigm for Excited-State Intramolecular Charge Transfer, J. Am. Chem. Soc., 127, 4170-4171, 2005.
• [22] Sen P., Atmaca G.Y., Erdogmus A., Kanmazalp S.D., Dege N., Yildiz S.Z., Peripherally tetra-benzimidazole units-substituted zinc(II) phthalocyanines: Synthesis, characterization and investigation of photophysical and photochemical properties, J. Lumin., 194, 123-130, 2018.
• [23] Lugovik K.I., Eltyshev A.K., Suntsova P.O., Smoluk L.T., Belousova A.V., Ulitko M.V., Minin A.S., Slepukhin P.A., Benassi E., Belskaya N.P., Fluorescent boron complexes based on new N,O-chelates as promising candidates for flow cytometry, Org. Biomol. Chem., 16, 5150–5162, 2018.
• [24] Sen P., Atmaca G.Y., Erdoğmuş A., Dege N., Genç H., Atalay Y., Yildiz S. Z., The synthesis, characterization, crystal structure and photophysical properties of a new meso-BODIPY substituted phthalonitrile, J. Fluoresc. 25, 1225-1234, 2015.