1,3-dimetil-5-(3,5-dimetilfenil)aminometilenbarbitürat bor diflorür kompleksinin sentezi, karakterizasyonu ve fotofiziksel özelliklerinin incelenmesi

Yıl 2019, , 135 - 140, 30.09.2019

Erkan Fırıncı

https://doi.org/10.30728/boron.527576

Öz

Sunulan çalışmada, barbitürik asitten türevlendirilen
1,3-dimetil-5-(3,5-dimetilfenil)aminometilenbarbitürat ve
1,3-dimetil-5-(3,5-dimetilfenil)aminometilenbarbitürat bor diflorür kompleksi
başarılı bir şekilde sentezlenmiştir. Sentezlenen bileşiklerin yapısal
karakterizasyonları elementel analiz, ATR FTIR ve NMR spektroskopileri
kullanılarak yapılmıştır. Sentezlenen bileşiklerin lüminesans özelliğe sahip
oldukları mor ötesi ve görünür bölge absorpsiyon spektroskopisi ve floresans emisyon
spektroskopisi kullanılarak belirlenmiştir. Komplekste bulunan BF2
grubunun emisyon bandını kırmızı bölgeye kaydırdığı tespit edilmiştir. Elde
edilen bulgular yeni lüminesans bor bileşiklerinin sentezlenebilmesi için
barbitürat iskeletinin önemli bir potansiyele sahip olduğunu göstermiştir.

Anahtar Kelimeler

Barbitürik asit, Bor diflorür kompleksi, Spektroskopi

Synthesis, characterization of 1,3-dimethyl-5-(3,5-dimethylphenyl)aminomethylenebarbiturate boron difluoride complex and investigation of photophysical properties

Öz

In the present study, 1,3-dimethyl-5-(3,5-dimethylphenyl)aminomethylenebarbiturate
and 1,3-dimethyl-5-(3,5-dimethylphenyl)aminomethylenebarbiturate boron
difluoride complex were successesfully prepared. The characterizations of
synthesized compounds were done by using elemental analysis, ATR FTIR and NMR
spectroscopies. The synthesized compounds were determined to have luminescence
properties by using ultraviolet-visible absorption and fluorescence emission
spectroscopies. It was determined that the BF2 group in the complex
shifted the emission band to the red zone. The results showed that the
barbiturate framework has a great potential for the synthesis of new
luminescence boron compounds.

Anahtar Kelimeler

Barbituric acid, Boron difluoride complex, Spectroscopy

Kaynakça

• [1] Chen P. Z., Niu L. Y., Chen Y. Z. , Yang Q.Z., Difluoroboron β-diketonate dyes: Spectroscopic properties and applications, Coord. Chem. Rev., 350, 196-216, 2017.
• [2] Tanaka K., Chujo Y., Recent progress of optical functional nanomaterials based on organoboron complexes with β-diketonate, ketoiminate and diiminate, NPG Asia Mater., 7, e223, 2015.
• [3] Yuan L., Lin W., Zheng K., He L., Huang W., Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging, Chem. Soc. Rev., 42, 622-661, 2013.
• [4] Turksoy A., Yildiz D., Akkaya E. U. Photosensitization and controlled photosensitization with BODIPY dyes, Coord. Chem. Rev., 379, 47-64, 2019.
• [5] Kolemen S., Akkaya E. U., Reaction-based BODIPY probes for selective bio-imaging, Coord. Chem. Rev., 354, 121-134, 2018.
• [6] Kolemen S., Cakmak Y., Ozdemir T., Erten-Ela S., Buyuktemiz M., Dede Y., Akkaya E. U., Design and characterization of Bodipy derivatives for bulk heterojunction solar cells, Tetrahedron, 70, 6229-6234, 2014.
• [7] Kim S., Ohulchanskyy T. Y., Pudavar H. E., Pandey R. K., Prasad P. N., Organically modified silica nanoparticles co-encapsulating photosensitizing drug and aggregation-enhanced two-photon absorbing fluorescent dye aggregates for two-photon photodynamic therapy, J. Am. Chem. Soc., 129, 2669-2675, 2007.
• [8] Loudet A., Burgess K., BODIPY Dyes and their derivatives: Syntheses and spectroscopic properties, Chem. Rev., 107, 4891-4932, 2007.
• [9] Frath D., Massue J., Ulrich G., Ziessel R., Luminescent Materials: Locking π‐Conjugated and Heterocyclic Ligands with Boron(III), Angew. Chem. Int. Ed., 53, 2290-2310, 2014.
• [10] Zhang F., Liu O., Chen Y., Zhai L., Liu M., Sun J., Mi W., Sun M., Lu R., Mechanofluorochromism of D–π–A-Type difluoroboron β-carbonyl cyclic ketonate complexes that contain a carbazole unit, Asian J. Org. Chem., 6, 1659-1666,2017.
• [11] Perumal K., Garg J. A., Blacque O, Saiganesh R., Kabilan S., Balasubramanian K. K., Venkatesan K., β-Iminoenamine-BF2 complexes: Aggregation-induced emission and pronounced effects of aliphatic rings on radiationless deactivation, Chem. Asian J., 7, 2670-2677, 2012.
• [12] Dousova H., Simunek P., Almonasy N., Ruzickova Z., Synthesis, NMR, X-ray and Uv/Vis characterization and preliminary luminescence study of some boron b-iminoenolates having 6-aminocoumarin moiety, J. Organomet. Chem., 802, 60-71, 2016.
• [13] Fırıncı E., Giziroğlu E., Celepci Barut D., Söyleyici C. H., Aygün M., Spiro copper(II)-metallacycles derived from 5-arylaminomethylene-barbituric acids: Synthesis and structural characterization, J. Mol. Struct., 1137, 113-118, 2017.
• [14] Neumann D. M., Cammarata A., Backes G., Palmer G. E., Jursic B. S., Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones, Bioorg. Med. Chem., 22, 813-826, 2014.
• [15] Bamoniri A., Mirjalili B. B. F., Moshtael-Arani N., Nano BF3•SiO2: A green heterogeneous solid acid for synthesis of formazan dyes under solvent-free condition, J. Mol. Catal. A: Chem., 393, 272-278, 2014.
• [16] Bonacorsoa G. H., Calheiroa P. T., Acunhab V. T., Iglesiasb A. B., Franceschinia Z. S., Ketzera A., Meyera R. A, Nogarac A. P., Rochac B. T. J., Zanattaa N., Martins A. P. M., Novel aryl(heteroaryl)-substituted (pyrimidyl)benzamide-based BF2 complexes: Synthesis, photophysical properties, BSA-binding, and molecular docking analysis, Dyes Pigm., 161, 396-402, 2019.
• [17] Hisamune Y., Kim T., Nishimura K., Ishida M., Toganoh M., Mori S., Kim D., Furuta H., Switch-ON Near IR Fluorescent Dye Upon Protonation: Helically Twisted Bis(Boron Difluoride) Complex of p-Extended Corrorin, Chem. Eur. J., 24, 4628-4634, 2018.
• [18] Liu C., Zhang H., Zhao J., Synthesis, characterization and properties of furan-containing difluoroboron complexes, RSC Adv., 95, 92341-92348, 2016.