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Year 2016, Volume: 3 Issue: 3, 683 - 706, 08.01.2017
https://doi.org/10.18596/jotcsa.287303

Abstract

References

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Synthesis, characterization and investigation of the spectroscopic properties of novel peripherally 2,3,5-trimethylphenoxy substituted Cu and Co phthalocyanines, the computational and experimental studies of the 4-(2,3,5-trimethylphenoxy)phthalonitrile

Year 2016, Volume: 3 Issue: 3, 683 - 706, 08.01.2017
https://doi.org/10.18596/jotcsa.287303

Abstract

4-(2,3,5-trimethylphenoxy)phthalonitrile (3) was firstly prepared via aromatic nucleophilic substitution reaction and characterized by FT-IR, mass spectrometry, 1H and 13C NMR techniques. The molecular structure of the compound (3) was optimized using Density Functional Theory (DFT/B3LYP) method with 6-311G(d,p) basis set in the ground state. The molecular geometric parameters which were obtained by X-ray single crystal diffraction method and the spectral results were compared with computed bond lengths and angles, vibrational frequencies and 1H, 13C NMR chemical shifts values of the compound (3). Also, Cu(II) and Co(II) phthalocyanines were synthesized by the treatment of dinitrile derivative with anhydrous CuCl2 or CoCl2 under N2 atmosphere in dry n-pentanol at 140oC. The new compounds have been determined by elemental analysis, FT-IR and electronic absorption. The UV-Vis spectra of the Cu(II) and Co(II) phthalocyanines were recorded with different concentration in THF and also with different solvents as DMF, DMSO, DCM, CHCl3, toluene.

References

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  • Leznoff CC, Lever ABP. Phthalocyanines: Properties and Applications, vols. 1-4, VCH, Weinheim, 1998. ISBN: 978-0-471-18720-2 ; ISBN: 978-0-471-18828-5; ISBN: 978-0-471-18863-6; ISBN: 978-0-471-18629-8
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  • Ranyuk E, Cauchon, Klarskov, Guerin B, van Lier. Phthalocyanine–Peptide Conjugates: Receptor-Targeting Bifunctional Agents for Imaging and Photodynamic Therapy. J. Med. Chem. 2013 Jan; 56:4;1520–1534. DOI: 10.1021/jm301311c
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  • Gürel E, Pişkin M, Altun S, Odabaş Z, Durmuş M. Synthesis, characterization and investigation of the photophysical and photochemical properties of highly soluble novel metal-free, zinc(II), and indium(III) phthalocyanines substituted with 2,3,6-trimethylphenoxy moieties. Dalton Trans. 2015;44:6202-6211. DOI:10.1039/C5DT00304K
  • Ağar E, Şaşmaz S, Akdemir N, Keskin İ. Synthesis and Characterization of New Phthalocyanines Containing Four 15-Membered Tetrathiaoxa Macrocycles. Synth. React. Inorg. Met.-Org. Chem. 1999;29:3;473-485. DOI:10.1080/00945719909349463
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  • Özil M, Ağar E, Şaşmaz S, Kahveci B, Akdemir N, Gümrükçüoğlu İE. Microwave-assisted synthesis and characterization of the monomeric phthalocyanines containing naphthalene-amide group moieties and the polymeric phthalocyanines containing oxa-azabridge. Dyes and Pigments. 2007;75:3;732-740. DOI:10.1016/j.dyepig.2006.07.026
  • Kantar C, Akdemir N, Ağar E, Ocak N, Şaşmaz S. Microwave-assisted synthesis and characterization of differently substituted phthalocyanines containing 3,5-dimethoxyphenol and octanethiol moieties. Dyes and Pigments. 2007;76:1;7-12. DOI:10.1016/j.dyepig.2006.08.005
  • Akbal T, Akdemir N, Ağar E, Kantar C, Erdönmez A. 4-(2,3,5-trimethylphenoxy)phthalonitrile. Acta Cryst. E 2005 Aug;E61:8;o2630-o2631. DOI: 10.1107/S1600536805022592.
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There are 55 citations in total.

Details

Primary Language English
Subjects Electrochemistry
Journal Section Articles
Authors

Nesuhi Akdemir This is me

Publication Date January 8, 2017
Submission Date July 4, 2016
Published in Issue Year 2016 Volume: 3 Issue: 3

Cite

Vancouver Akdemir N. Synthesis, characterization and investigation of the spectroscopic properties of novel peripherally 2,3,5-trimethylphenoxy substituted Cu and Co phthalocyanines, the computational and experimental studies of the 4-(2,3,5-trimethylphenoxy)phthalonitrile. JOTCSA. 2017;3(3):683-706.