5-Amino-1,3,4-Tiyadiazol Sübstitüye Çinko(II) Ftalosiyanin Bileşiğinin Sentezi ve Spektroskopik Özellikleri
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.
Synthesis and Spectroscopic Properties of 5-Amino-1,3,4-Thiadiazole Substituted Zinc(II) Phthalocyanine Compound
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 werecharacterized by 1H-NMR, UV-vis and IR spectra. Aggregation behavior of compound 2 was investigatedboth in different solvents (CHCl3, DMF, DMSO) and in different concentrations. The fluorescence propertiesof compound 2 were also studied.
___
- 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.
- Bagher A.M., Introduction to Organic Solar
Cells, Sustain. Energy, 2 (2014) 85-90.
- 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.
- Li X., Wang H., Wu H., Phthalocyanines
and Their Analogs Applied in Dye-
Sensitized Solar Cell, Structure and
Bonding, 135 (2010) 229-274.
- Leznoff C.C., Lever A.B.P.
Phthalocyanines: properties and
applications. vols. 2-4. Cambridge: VCH
Publishers, 1989, 1993, 1996.
- McKeown N.B., Phthalocyanine materials.
Synthesis, structure and function.
Cambridge: Cambridge University Press,
1998.
- 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.
- 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.
- Özceşmeci İ., Gelir A., Gül A., Synthesis
and photophysical properties
phthalocyanineepyrene dyads, Dyes
Pigments, 92 (2012) 954-960.
- Sevim A.M., Arıkan S., Özçeşmeci İ., Gül
A., Photophysical properties
ofanthracenylmethyloxycarbonylmethylsulf
anyl-phthalocyanines, Synthetic Met., 183
(2013) 1-7.
- 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.
- 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.
- Thompson B.C. and Frechet J.M.J.,
Polymer–Fullerene Composite Solar Cells,
Angew. Chem. Int. Edit., 47 (2008) 58-77.
- 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.
- 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.
- Armarego W.L.F., Chai C.L.L., Purificaiton
of Laboratory Chemicals. Fifth ed. Tokyo:
Butterworth/Heinemann, 2003.
- 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.
- 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.
- 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.
- Nyokong T., Effects of substituents on the
photochemical and photophysical
properties of main group metal
phthalocyanines, Coord. Chem. Rev., 251
(2007) 1707-1722.
- Nyokong T., Electronic Spectral and
Electrochemical Behavior of Near Infrared
Absorbing Metallophthalocyanines,
Structure and Bonding, 135 (2010) 45-88.
- Leznoff C.C., Lever A.B.P.,
Phthalocyanines Properties and
Applications. Vol.1. Cambridge: VCH
Publisher, 1989.
- Durmuş M., Nyokong T.,
Photophysicochemical and fluorescence
quenching studies of benzyloxyphenoxysubstituted
zinc phthalocyanines,
Spectrochim. Acta A, 69 (2008) 1170-1177.
- 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.
- 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.
- 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.
Jacques P., Braun A.M., Laser Flash
Photolysis of Phthalocyanines in Solution
and Microemulsion, Helv. Chim. Acta, 64
(1981) 1800-1806.
- 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.