Gadolinyum(III) Asetat İçeren Yeni Tetrapirazinoporfirazinin Sentezi ve Spektroskopik Özellikleri

Year 2023, Volume: 23 Issue: 3, 602 - 607, 28.06.2023

Mehmet Pişkin , Zafer Odabaş , Mahmut Durmuş

https://doi.org/10.35414/akufemubid.1180731

Abstract

Yeni tetrakis-(2-metilpirazino)porfirazinato gadolinyum(III) asetat kompleksinin sentezlenip, saflaştırılmasının ardından yapısı element analiz, Fourier-Transform Kızılötesi, Ultraviyole görünür ve Floresan spektroskopi teknikleri ile karakterize edildi. Polar aprotik solvent olan ve yüksek dielektrik sabitine ve yüksek dipol momente sahip olan hem Dimetil sülfoksit hem de N,N-Dimetilformamid solventlerinde agregasyon yapmadan iyi bir şekilde çözünebilmektedir. Dimetil sülfoksitte hazırlanan belirli farklı konsantrasyon aralıklarındaki çözeltilerindeki agregasyon özelliği araştırılarak çoğunlukla monomerik türler içerdiği de belirlenmiştir. Ayrıca; dimetil sülfoksitte hazırlanan çözeltisinin floresan özellikleri incelenerek merkezinde ağır bir nadir toprak elementi olarak gadolinyum(III) asetat metal iyonunun etkisi belirlenmiştir. Tetrakis-(2-metilpirazino)porfirazinato gadolinyum(III) asetat, elektronik ve optik malzeme olarak ve fotokatalitik uygulamalar gibi çeşitli teknolojik uygulama alanlarında kullanılabilir ve pirazinoporfirazin benzeri formlardaki değişiklikleri içeren sistemler için de faydalı olabilir.

Keywords

Tetrapirazinoporfirazin, Gadolinyum(III) asetat, Sentez, Agregasyon, Spektroskopi

Project Number

FHD-2021-3364

Synthesis and Spectroscopic Properties of Newly Tetrapyrazinoporphyrazine Containing Gadolinium(III) Acetate

Abstract

A new tetrakis-(2-methylpyrazino)porphyrazinato gadolinium(III) acetate complex was synthesized. Elemental analysis, Fourier-Transform Infrared, Ultraviolet-visible, and fluorescence spectroscopy techniques clarified its structure. It can dissolve very well without aggregation in both Dimethyl sulfoxide and N, N-Dimethylformamide, which have high dielectric constant and high dipole moment from polar aprotic solvent type. Its aggregation property was also investigated in dimethyl sulfoxide at different concentrations, and it was determined to contain monomeric species. In addition, its fluorescence properties were investigated in Dimethyl sulfoxide and the effect of gadolinium(III) acetate metal ion as a heavy rare earth element was determined. According to the findings in this study, it may be used as an electronic and optical material and in various technological applications such as photocatalytic applications. In addition, these findings may be useful for systems that include changes in pyrazinoporphyrazine-like forms.

Keywords

Tetrapyrazinoporphyrazine, Gadolinium(III) acetate, Synthesis, Aggregation, Spectroscopic

Supporting Institution

Çanakkale Onsekiz Mart University the Scientific Research Coordination Unit

Project Number

FHD-2021-3364

Thanks

This work was supported by Çanakkale Onsekiz Mart University the Scientific Research Coordination Unit, Project number: FHD-2021-3364.

References

• Donzello, M.P., Ercolani, C., Novakova, V., Zimcik, P., and Stuzhin, P.A., 2016. Tetrapyrazinoporphyrazines and their metal derivatives. Part I: Synthesis and basic structural information. Coordination Chemistry Reviews, 309, 107–179.
• Donzello, M.P., Viola, E., Bergami, C., Dini, D., Ercolani, C., Giustini, M., Kadish, K.M., Meneghetti, M., Monacelli, F., Rosa, A., 2008. Tetra-2,3-pyrazinoporphyrazines with Externally Appended Pyridine Rings. Chemical and Redox Properties and Highly Effective Photosensitizing Activity for Singlet Oxygen Production of Penta- and Monopalladated Complexes in Dimethylformamide Solution. Inorganic Chemistry, 47, 8757–8766.
• Donzello, M.P., Viola, E., Cai, X., Mannina, L., Ercolani, C., Kadish, K.M., 2010. Tetra-2,3-pyrazinoporphyrazines with Externally Appended Pyridine Rings. Central (ZnII, CuII, MgII(H2O), CdII) and Exocyclic (PdII) Metal Ion Binding in Heteropentametallic Complexes from Tetrakis-2,3-[5,6-di(2-pyridyl)pyrazino]porphyrazine. Inorganic Chemistry, 49, 2447–2456.
• Kudrevich, S.V., van Lier, J.E., 1996. Azaanalogs of phthalocyanine: syntheses and properties. Coordination Chemistry Reviews, 156, 163-182
• Kopecky, K., Šatínský, D., Novakova, V., Miletin, M., Svoboda, A., Zimcik, P., 2011. Synthesis of mono-, di-, tri- and tetracarboxy azaphthalocyanines as potential dark quenchers. Dyes and Pigments, 91, 112–119.
• Kostka, M., Zimcik, P., Miletin, M., Klemera, P., Kopecky, K., Musil, Z., 2006. Comparison of aggregation properties and photodynamic activity of phthalocyanines and azaphthalocyanines. Journal of Photochemistry and Photobiology A: Chemistry, 178, 16–25.
• Lee, B.H., Jaung, J.Y., Jang, S.C., Yi, S.C., 2005. Synthesis and optical properties of push–pull type tetrapyrazinoporphyrazines. Dyes and Pigments, 65, 159–167.
• Novakova, V.; Donzello, M.P.; Ercolani, C.; Zimcik, P.; Stuzhin, P.A., 2018. Tetrapyrazinoporphyrazines and their metal derivatives. Part II: Electronic structure, electrochemical, spectral, photophysical and other application related properties. Coordination Chemistry Reviews, 361, 1–73.
• Park, J.M.; Song, C.J.; Yao, W.; Jung, C.Y.; Hyun, I.H.; Seong, D.H.; Jaung, J.Y., 2015. Synthesis of carbohydrate-conjugated azaphthalocyanine complexes for PDT. Tetrahedron Letters, 56, 4967–4970.
• Park, J.M., Jung, C.Y., Song, C.J., Jaung, J.Y., 2015. Synthesis and photophysical properties of axially substituted silicon(IV) tetrapyrazinoporphyrazines. Inorganic Chemistry Communications, 62, 64– 66.
• Svec, J., Zimcik, P., Novakova, L., Rakitin, O.A., Amelichev, S.A., Stuzhin, P.A., and Novakova, V., 2015. 1,2,5-Chalcogenadiazole-Annulated Tripyrazinoporphyrazines: Synthesis, Spectral Characteristics, and Influence of the Heavy Atom Effect on Their Photophysical Properties. European Journal of Organic Chemistry, 3, 596-604.
• Tomachynskyi, S., Korobko, S., Tomachynski, L., Pavlenko, V., 2011. Synthesis and spectral properties of new tetrakis-2,3-{5,7-bis[(E)-2-(4-methylphenyl)vinyl] pyrazino}porphyrazine metal complexes. Optical Materials, 33, 1553–1556.
• Zimcik, P., Novakova V., Kopecky K., Miletin M., Uslu Kobak R.Z., Svandrlikova E., Váchová L., Lang K., 2012. Magnesium Azaphthalocyanines: An Emerging Family of Excellent Red-Emitting Fluorophores. Inorganic Chemistry, 51, 4215–4223.