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Synthesis and Spectroscopic Properties of 5-Amino-1,3,4-Thiadiazole Substituted Zinc(II) Phthalocyanine Compound

Year 2018, Volume: 39 Issue: 4, 812 - 817, 24.12.2018

Ebru Yabaş

https://doi.org/10.17776/csj.457964
Cited By: 1

Abstract

Thiadiazole substituted phthalonitrile 1 was prepared by a nucleophilic
displacement reaction of 4-nitrophthalonitrile with
5-Amino-1,3,4-thiadiazole-2-thiole.
Thiadiazole tetrasubstituted zinc(II) monophthalocyanine 2 was synthesized by tetramerization of compound 1. The new compounds were characterized by 1H-NMR, UV-vis and IR spectra.
Aggregation behavior of compound 2
was investigated both in different solvents (CHCl3, DMF, DMSO) and
in different concentrations. The fluorescence properties of compound 2 were also studied.

Keywords

Phthalocyanine thiadiazole organic solar cells aggregation zinc

References

  • [1]. Xu X., Yu T., Bi Z., Ma W., Li Y., Peng Q., Realizing Over 13% Efficiency in Green-Solvent-Processed Nonfullerene Organic Solar Cells Enabled by 1,3,4-Thiadiazole-Based Wide-Bandgap Copolymers, Adv. Mater., 30 (2018) 1703973.
  • [2]. Bagher A.M., Introduction to Organic Solar Cells, Sustain. Energy, 2 (2014) 85-90.
  • [3]. Peng Y., Zhang L., Cheng N., Andrew T.L., ITO-Free Transparent Organic Solar Cell with Distributed Bragg Reflector for Solar HarvestingWindows, Energies, 10 (2017) 707-720.
  • [4]. Li X., Wang H., Wu H., Phthalocyanines and Their Analogs Applied in Dye-Sensitized Solar Cell, Structure and Bonding, 135 (2010) 229-274.
  • [5]. Leznoff C.C., Lever A.B.P. Phthalocyanines: properties and applications. vols. 2-4. Cambridge: VCH Publishers, 1989, 1993, 1996.
  • [6]. McKeown N.B., Phthalocyanine materials. Synthesis, structure and function. Cambridge: Cambridge University Press, 1998.
  • [7]. Altın Ş., Dumludağ F., Oruç Ç., Altındal A., Influence of humidity on kinetics of xylene adsorption onto ball-type hexanuclear metallophthalocyanine thin film, Microelectron. Eng., 134 (2015) 7-13.
  • [8]. Shi J., Luan L., Fang W., Zhao T., Liu W., Cui D., High-sensitive low-temperature NO2 sensor based on Zn (II) phthalocyanine with liquid crystalline properties, Sensor. Actuat. B-Chem., 204 (2014) 218-223.
  • [9]. Özceşmeci İ., Gelir A., Gül A., Synthesis and photophysical properties phthalocyanineepyrene dyads, Dyes Pigments, 92 (2012) 954-960.
  • [10]. Sevim A.M., Arıkan S., Özçeşmeci İ., Gül A., Photophysical properties ofanthracenylmethyloxycarbonylmethylsulfanyl-phthalocyanines, Synthetic Met., 183 (2013) 1-7.
  • [11]. Cho K.T., Trukhina O., Roldán-Carmona C., Ince M., Gratia P., Grancini G., Gao P., Marszalek T., Pisula W., Reddy P.Y., Torres T., Nazeeruddin M.K., Molecularly Engineered Phthalocyanines as Hole-Transporting Materials in Perovskite Solar Cells Reaching Power Conversion Efficiency of 17.5%, Adv. Energy Mater., 7 (2017) 1601733.
  • [12]. Hu Y., Li C.Y., Wang X.M., Yang Y.H., Zhu H.L., 1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry, Chem. Rev., 114 (2014) 5572-5610.
  • [13]. Thompson B.C. and Frechet J.M.J., Polymer–Fullerene Composite Solar Cells, Angew. Chem. Int. Edit., 47 (2008) 58-77.
  • [14]. Tian H., Yu Z., Hagfeldt A., Kloo L., Sun L., Organic Redox Couples and Organic Counter Electrode for Efficient Organic Dye-Sensitized Solar Cells, J. Am. Chem. Soc., 133 (2011) 9413-9422.
  • [15]. Pang H., Skabara P.J., Crouch D.J., Duffy W., Heeney M., McCulloch I., Coles S.J., Horton P.N., Hursthouse M.B., Structural and Electronic Effects of 1,3,4-Thiadiazole Units Incorporated into Polythiophene Chains, Macromolecules, 40 (2007) 6585-6593.
  • [16]. Armarego W.L.F., Chai C.L.L., Purificaiton of Laboratory Chemicals. Fifth ed. Tokyo: Butterworth/Heinemann, 2003.
  • [17]. Wöhrle D., Eskes M., Shigehara K., Yamada A., A Simple Synthesis of 4,5-Disubstituted 1,2-Dicyanobenzenes and 2,3,9,10,16,17,23,24-Octasubstituted Phthalocyanines, Synthesis, 2 (1993) 194-196.
  • [18]. Yabaş E., Sülü M., Saydam S., Dumludağ F., Salih B., Bekaroğlu Ö., Synthesis, characterization and investigation of electrical and electrochemical properties of imidazole substituted phthalocyanines, Inorg. Chim. Acta, 365 (2011) 340-348.
  • [19]. Yabaş E., Sülü M., Dumludağ F., Salih B., Bekaroğlu Ö., Imidazole octasubstituted novel mono and double-decker phthalocyanines: Synthesis, characterization, electrical and gas sensing properties, Polyhedron, 153 (2018) 51-63.
  • [20]. Nyokong T., Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines, Coord. Chem. Rev., 251 (2007) 1707-1722.
  • [21]. Nyokong T., Electronic Spectral and Electrochemical Behavior of Near Infrared Absorbing Metallophthalocyanines, Structure and Bonding, 135 (2010) 45-88. [22]. Leznoff C.C., Lever A.B.P., Phthalocyanines Properties and Applications. Vol.1. Cambridge: VCH Publisher, 1989.
  • [23]. Durmuş M., Nyokong T., Photophysicochemical and fluorescence quenching studies of benzyloxyphenoxy-substituted zinc phthalocyanines, Spectrochim. Acta A, 69 (2008) 1170-1177.
  • [24]. Ogunsipe A., Nyokong T., Effects of substituents and solvents on the photochemical properties of zinc phthalocyanine complexes and their protonated derivatives, J. Mol. Struct., 689 (2004) 89-97.
  • [25]. Fery-Forgues S., Lavabre D., Are Fluorescence Quantum Yields So Tricky to Measure? A Demonstration Using Familiar Stationery Products, J. Chem. Educ., 76 (1999) 1260-1264.
  • [26]. Maree D., Nyokong T., Suhling K., Phillips D., Effects of axial ligands on the photophysical properties of silicon octaphenoxyphthalocyanine, J. Porphyr. Phthalocya., 6 (2002) 373-376.
  • [27]. Jacques P., Braun A.M., Laser Flash Photolysis of Phthalocyanines in Solution and Microemulsion, Helv. Chim. Acta, 64 (1981) 1800-1806.
  • [28]. Durmuş M., Nyokong T., Synthesis and solvent effects on the electronic absorption and fluorescence spectral properties of substituted zinc phthalocyanines, Polyhedron, 26 (2007) 2767-2776.

5-Amino-1,3,4-Tiyadiazol Sübstitüye Çinko(II) Ftalosiyanin Bileşiğinin Sentezi ve Spektroskopik Özellikleri

Year 2018, Volume: 39 Issue: 4, 812 - 817, 24.12.2018

Ebru Yabaş

https://doi.org/10.17776/csj.457964
Cited By: 1

Abstract

Tiyadiazol sübstitüye ftalonitril 1, 5-Amino-l, 3,4-tiyadiazol-2-tiyol
ile 4-nitroftalonitrilin nükleofilik yer değiştirme reaksiyonu ile hazırlandı.
Bileşik 1’in tetramerizasyonu ile
tiyadiazol tetrasübstitüye çinko(II) monoftalosiyanin 2 sentezlendi. Yeni bileşikler, 1H-NMR, UV-vis ve IR
spektrumları ile karakterize edildi. Bileşik 2'nin agregasyon davranışı hem farklı çözücülerde (CHCl3,
DMF, DMSO) hem de farklı konsantrasyonlarda araştırılmıştır. Bileşik 2'nin floresans özellikleri de
incelenmiştir.

Keywords

Ftalosiyanin tiyadiazol agregasyon çinko

References

  • [1]. Xu X., Yu T., Bi Z., Ma W., Li Y., Peng Q., Realizing Over 13% Efficiency in Green-Solvent-Processed Nonfullerene Organic Solar Cells Enabled by 1,3,4-Thiadiazole-Based Wide-Bandgap Copolymers, Adv. Mater., 30 (2018) 1703973.
  • [2]. Bagher A.M., Introduction to Organic Solar Cells, Sustain. Energy, 2 (2014) 85-90.
  • [3]. Peng Y., Zhang L., Cheng N., Andrew T.L., ITO-Free Transparent Organic Solar Cell with Distributed Bragg Reflector for Solar HarvestingWindows, Energies, 10 (2017) 707-720.
  • [4]. Li X., Wang H., Wu H., Phthalocyanines and Their Analogs Applied in Dye-Sensitized Solar Cell, Structure and Bonding, 135 (2010) 229-274.
  • [5]. Leznoff C.C., Lever A.B.P. Phthalocyanines: properties and applications. vols. 2-4. Cambridge: VCH Publishers, 1989, 1993, 1996.
  • [6]. McKeown N.B., Phthalocyanine materials. Synthesis, structure and function. Cambridge: Cambridge University Press, 1998.
  • [7]. Altın Ş., Dumludağ F., Oruç Ç., Altındal A., Influence of humidity on kinetics of xylene adsorption onto ball-type hexanuclear metallophthalocyanine thin film, Microelectron. Eng., 134 (2015) 7-13.
  • [8]. Shi J., Luan L., Fang W., Zhao T., Liu W., Cui D., High-sensitive low-temperature NO2 sensor based on Zn (II) phthalocyanine with liquid crystalline properties, Sensor. Actuat. B-Chem., 204 (2014) 218-223.
  • [9]. Özceşmeci İ., Gelir A., Gül A., Synthesis and photophysical properties phthalocyanineepyrene dyads, Dyes Pigments, 92 (2012) 954-960.
  • [10]. Sevim A.M., Arıkan S., Özçeşmeci İ., Gül A., Photophysical properties ofanthracenylmethyloxycarbonylmethylsulfanyl-phthalocyanines, Synthetic Met., 183 (2013) 1-7.
  • [11]. Cho K.T., Trukhina O., Roldán-Carmona C., Ince M., Gratia P., Grancini G., Gao P., Marszalek T., Pisula W., Reddy P.Y., Torres T., Nazeeruddin M.K., Molecularly Engineered Phthalocyanines as Hole-Transporting Materials in Perovskite Solar Cells Reaching Power Conversion Efficiency of 17.5%, Adv. Energy Mater., 7 (2017) 1601733.
  • [12]. Hu Y., Li C.Y., Wang X.M., Yang Y.H., Zhu H.L., 1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry, Chem. Rev., 114 (2014) 5572-5610.
  • [13]. Thompson B.C. and Frechet J.M.J., Polymer–Fullerene Composite Solar Cells, Angew. Chem. Int. Edit., 47 (2008) 58-77.
  • [14]. Tian H., Yu Z., Hagfeldt A., Kloo L., Sun L., Organic Redox Couples and Organic Counter Electrode for Efficient Organic Dye-Sensitized Solar Cells, J. Am. Chem. Soc., 133 (2011) 9413-9422.
  • [15]. Pang H., Skabara P.J., Crouch D.J., Duffy W., Heeney M., McCulloch I., Coles S.J., Horton P.N., Hursthouse M.B., Structural and Electronic Effects of 1,3,4-Thiadiazole Units Incorporated into Polythiophene Chains, Macromolecules, 40 (2007) 6585-6593.
  • [16]. Armarego W.L.F., Chai C.L.L., Purificaiton of Laboratory Chemicals. Fifth ed. Tokyo: Butterworth/Heinemann, 2003.
  • [17]. Wöhrle D., Eskes M., Shigehara K., Yamada A., A Simple Synthesis of 4,5-Disubstituted 1,2-Dicyanobenzenes and 2,3,9,10,16,17,23,24-Octasubstituted Phthalocyanines, Synthesis, 2 (1993) 194-196.
  • [18]. Yabaş E., Sülü M., Saydam S., Dumludağ F., Salih B., Bekaroğlu Ö., Synthesis, characterization and investigation of electrical and electrochemical properties of imidazole substituted phthalocyanines, Inorg. Chim. Acta, 365 (2011) 340-348.
  • [19]. Yabaş E., Sülü M., Dumludağ F., Salih B., Bekaroğlu Ö., Imidazole octasubstituted novel mono and double-decker phthalocyanines: Synthesis, characterization, electrical and gas sensing properties, Polyhedron, 153 (2018) 51-63.
  • [20]. Nyokong T., Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines, Coord. Chem. Rev., 251 (2007) 1707-1722.
  • [21]. Nyokong T., Electronic Spectral and Electrochemical Behavior of Near Infrared Absorbing Metallophthalocyanines, Structure and Bonding, 135 (2010) 45-88. [22]. Leznoff C.C., Lever A.B.P., Phthalocyanines Properties and Applications. Vol.1. Cambridge: VCH Publisher, 1989.
  • [23]. Durmuş M., Nyokong T., Photophysicochemical and fluorescence quenching studies of benzyloxyphenoxy-substituted zinc phthalocyanines, Spectrochim. Acta A, 69 (2008) 1170-1177.
  • [24]. Ogunsipe A., Nyokong T., Effects of substituents and solvents on the photochemical properties of zinc phthalocyanine complexes and their protonated derivatives, J. Mol. Struct., 689 (2004) 89-97.
  • [25]. Fery-Forgues S., Lavabre D., Are Fluorescence Quantum Yields So Tricky to Measure? A Demonstration Using Familiar Stationery Products, J. Chem. Educ., 76 (1999) 1260-1264.
  • [26]. Maree D., Nyokong T., Suhling K., Phillips D., Effects of axial ligands on the photophysical properties of silicon octaphenoxyphthalocyanine, J. Porphyr. Phthalocya., 6 (2002) 373-376.
  • [27]. Jacques P., Braun A.M., Laser Flash Photolysis of Phthalocyanines in Solution and Microemulsion, Helv. Chim. Acta, 64 (1981) 1800-1806.
  • [28]. Durmuş M., Nyokong T., Synthesis and solvent effects on the electronic absorption and fluorescence spectral properties of substituted zinc phthalocyanines, Polyhedron, 26 (2007) 2767-2776.
There are 27 citations in total.

Details

Primary Language English
Journal Section Natural Sciences
Authors

Ebru Yabaş

Publication Date December 24, 2018
Submission Date September 7, 2018
Acceptance Date October 23, 2018
Published in Issue Year 2018Volume: 39 Issue: 4

Cite

APA Yabaş, E. (2018). Synthesis and Spectroscopic Properties of 5-Amino-1,3,4-Thiadiazole Substituted Zinc(II) Phthalocyanine Compound. Cumhuriyet Science Journal, 39(4), 812-817. https://doi.org/10.17776/csj.457964

Cited By

Experimental and In Silico studies on optical properties of new thiadiazole tetrasubstituted metal-free and zinc phthalocyanine compounds
Optical Materials
https://doi.org/10.1016/j.optmat.2021.111808