Skip to main content
Log in

Synthesis, Spectral, and Fluorescence Studies of Fluorophenyl Methoxy Substituted Nickel Phthalocyanine Complex

  • RESEARCH
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

The synthesis, characterization, spectral, fluorescence properties of bis(4-fluorophenyl)-methoxy substituted nickel phthalocyanine were reported for the first time. The new compound has been characterized by elemental analysis, UV–Vis, FT-IR, 1H-NMR and mass spectra. The aggregation behaviour of this compound was investigated in the different solvent and concentrations of in CHCl3. Phthalocyanine complex did not show any aggregations. The fluorescent properties of the compound in five different solvents such as CHCl3 CH2Cl2 THF, DMF, DMSO were explained. Phthalocyanine complex gave the highest fluorescence quantum yield in CHCl3 and the lowest fluorescence quantum yield in DMSO.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

Availability of Data and Materials

Not applicable.

References

  1. Lever ABP, Leznoff CC (1996) Phthalocyanine: properties and applications. VCH, New York, Vol. 4

  2. McKeown NB (1998) Phthalocyanines materials-synthesis, structure and function. Cambridge University Press, New York

    Google Scholar 

  3. Kadish KM, Smith KM, Guilard R (2000–2003) The porphyrin handbook. 1–20. Academic, San Diego

  4. Jiang J, Kasuga K, Arnold DP (2001) Sandwich-type phthalocyaninato and porphyrinatometal complexes. In: Nalwa HS (ed) Supramolecular photo-sensitive and electroactive materials. Academic, New York, pp 113–210

    Chapter  Google Scholar 

  5. Erk P, Hengelsberg H (2003) Phthalocyanine dyes and pigments. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook, vol 19. Academic Press, San Diego, p 105

  6. de la Torre G, Claessens CG, Torres T (2007) Phthalocyanines: old dyes, new materials. Putting color in nanotechnology. Chem Commun 2000–15. https://doi.org/10.1039/B614234F

  7. Claessens CG, Hahn U, Torres T (2008) Phthalocyanines: From outstanding electronic properties to emerging applications. Chem Rec 8:75. https://doi.org/10.1002/tcr.20139

    Article  CAS  PubMed  Google Scholar 

  8. Mustroph H, Stollenwerk M, Bressau V (2006) Current developments in optical data storage with organic dyes. Angew Chem Int Ed 45:2016. https://doi.org/10.1002/anie.200502820

    Article  CAS  Google Scholar 

  9. Ben-Hur E, Chan WS (2003) Phthalocyanines in photobiology and their medical applications In: Kadish KM, Smith KM, Guilard R (eds) Porphyrin handbook, phthalocyanine properties and materials, vol 19, Chap. 117. Academic Press, New York

  10. Li L, Tang Q, Li H, Hu W, Yang X, Shuai Z, Liu Y, Zhu D (2008) Organic thin-film transistors of phthalocyanines. Pure Appl Chem 80:2231. https://doi.org/10.1351/pac200880112231

    Article  CAS  Google Scholar 

  11. Tang ML, Oh JH, Reichardt AD, Bao Z (2009) Chlorination: A General Route toward Electron Transport in Organic Semiconductors. J Am Chem Soc 131:3733. https://doi.org/10.1021/ja809045s

    Article  CAS  PubMed  Google Scholar 

  12. Snow AW (2003) Phthalocyanine aggregation. In: Kadish KM, Smith KM, Guilard R (eds) Porphyrin handbook, phthalocyanine properties and materials, vol 17, Chap 109. Academic Press, New York

  13. Cid JJ, García-Iglesias M, Yum JH, Forneli A, Albero J, Martínez-Ferrero E, Vázquez P, Grätzel M, Nazeeruddin MK, Palomares E, Torres T (2009) Molecular cosensitization for efficient panchromatic dye-sensitized solar cells. Chem Eur J 15:5130. https://doi.org/10.1002/anie.200703106

    Article  CAS  PubMed  Google Scholar 

  14. Meunier B, Sorokin A (1997) Oxidation of Pollutants Catalyzed by Metallophthalocyanines. Acc Chem Res 30:470–476. https://doi.org/10.1021/ar960275c

    Article  CAS  Google Scholar 

  15. Tao X, Ma W, Zhang T, Zhao J (2002) A novel approach for the oxidative degradation of organic pollutants in aqueous solutions mediated by iron tetrasulfophthalocyanine under visible light radiation. Chem Eur J 8:1321–1326. https://doi.org/10.1002/1521-3765(20020315)8:6%3c1321::AID-CHEM1321%3e3.0.CO;2-M

    Article  CAS  PubMed  Google Scholar 

  16. Ali H, van Lier JE (1999) Metal complexes as photo- and radiosensitizers. Chem Rev 99:2379. https://doi.org/10.1021/cr980439y

    Article  CAS  PubMed  Google Scholar 

  17. Liu JY, Lo PC, Jiang XJ, Fong WP, Ng DKP (2009) Synthesis and in vitro photodynamic activities of di-α-substituted zinc(ii) phthalocyanine derivatives. Dalton Trans 4129–4135. https://doi.org/10.1039/b817940a

  18. Wie S, Huang D, Li L, Meng Q (2003) Synthesis and properties of some soluble metallophthalocyanines trifluromethylphenyoxy moiety. Dyes Pigm 56:1–6. https://doi.org/10.1016/S0143-7208(02)00104-3

    Article  Google Scholar 

  19. Özçeşmeci M, Özkan E, Hamuryudan E (2013) Synthesis, characterization, and aggregation properties of functionalized polyfluorinated metallo-phthalocyanines. J Porphyrins Phthalocyanines 17:1–8. https://doi.org/10.1142/S1088424613500764

    Article  CAS  Google Scholar 

  20. Farajzadeh N, Karaoğlu HP, Akin M, Saki N, Koçak MB (2019) Synthesis, Photophysical and Biological Properties of New Phthalocyanines Bearing Peripherally 4-(Trifluoromethoxy) phenoxy Groups. Inorg Chem 4:8998. https://doi.org/10.1002/slct.201901509

    Article  CAS  Google Scholar 

  21. Kırbac E, Atmaca G, Erdoğmuş A (2014) Novel highly soluble fluoro, chloro, bromo-phenoxy-phenoxy substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties. J Organomet Chem 752:115. https://doi.org/10.1016/j.jorganchem.2013.12.005

    Article  CAS  Google Scholar 

  22. Kilicarslan FA (2015) New soluble bis (4-fluorophenyl)-methoxy substituted phthalocyanines: synthesis, characterization, spectral, aggregation and fluorescence studies. J Chem Eng Chem Res 2:706

    CAS  Google Scholar 

  23. Erdoğmuş A, Nyokong T (2009) New soluble methylendioxy-phenoxy-substituted zinc phthalocyanine derivatives: Synthesis, photophysical and photochemical studies. Polyhedron 28:2855–2862. https://doi.org/10.1016/j.poly.2009.06.019

    Article  CAS  Google Scholar 

  24. Erdoğmuş A, Nyokong T (2010) Novel, soluble, FluXoro functional substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties. Dyes Pigm 86:174–181. https://doi.org/10.1016/j.dyepig.2010.01.001

    Article  CAS  Google Scholar 

  25. Öztürk C, Erdoğmuş A, Durmuş M, Uğur AL, Kılıçarslan FA, Erden İ (2012) Highly soluble 3,4-(dimethoxyphenylthio) substituted phthalocyanines: Synthesis, photophysical and photochemical studies. Spectrochim Acta A 86:423–431. https://doi.org/10.1016/j.saa.2011.10.062

    Article  CAS  Google Scholar 

  26. Gouterman M (1978) In: Dolphin D (ed) The Porphyrins, vol. 3. Academic Press, NewYork

  27. Engelkamp H, Nolte RJM (2000) Molecular materials based on crown ether functionalized phthalocyanines. J Porphyrins Phthalocyanines 4:454–459. https://doi.org/10.1002/1099-1409(200008)4:5%3c454::AID-JPP261%3e3.0.CO;2-D

    Article  CAS  Google Scholar 

  28. Bıyıklıoğlu Z, Çakır V, Çakır D, Kantekin H (2014) Crown ether-substituted water soluble phthalocyanines and their aggregation, electrochemical studies. J Organomet Chem 749:18–25. https://doi.org/10.1016/j.jorganchem.2013.07.079

    Article  CAS  Google Scholar 

  29. Senge MO, Renner MW, Kalisch WW, Fajer J (2000) Molecular structure of (5,10,15,20-tetrabutyl-2,3,7,8,12,13,17,18-octaethylporphyrinato) nickel(II)-correlation of nonplanarity with frontier orbital shifts. J Chem Soc Dalton Trans 381–385. https://doi.org/10.1039/A905927J

  30. Idowu M, Nyokong T (2008) Synthesis, photophysics and photochemistry of tin (IV) phthalocyanine derivatives. J Photoch Photobio A Chem 199:282–290. https://doi.org/10.1016/j.jphotochem.2008.06.007

    Article  CAS  Google Scholar 

  31. Chauke V, Durmuş M, Nyokong T (2007) Photochemistry, photophysics and nonlinear optical parameters of phenoxy and tert-butyl phenoxy substituted indium(III) phthalocyanines. J Photochem Photobiol A 192:179–187. https://doi.org/10.1016/j.jphotochem.2007.05.022

    Article  CAS  Google Scholar 

  32. Dini D, Hanack, M (2003) Physical properties of phthalocyanine-based materials In: Kadish KM, SmithKM, Guilard R (eds) Porphyrin handbook, phthalocyanine properties and materials, vol 17, Chap. 107. Academic Press, New York

  33. O’Regan BC, López-Duarte I, Martínez-Díaz MV, Forneli A, Albero J, Morandeira A, Palomares E, Torres T, Durran JR (2008) Catalysis of recombination and its limitation on open circuit voltage for dye sensitized photovoltaic cells using phthalocyanine dyes. J Am Chem Soc 130:2906–2907. https://doi.org/10.1021/ja078045o

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This research has been supported by Yıldız Technical University Scientific Research Projects Coordination Department. Project Number: 2014-01-02-GEP02. I would like to thank Prof. Dr. Ali ERDOĞMUŞ for his valuable contributions.

Funding

This research has been supported by Yıldız Technical University Scientific Research Projects Coordination Department. Project Number: 2014–01-02-GEP02.

Author information

Authors and Affiliations

Authors

Contributions

Material synthesis, purification and characterization studies, spectral measurements and writing of the article were carried out by Fatma Aytan Kılıçarslan.

Corresponding author

Correspondence to Fatma Aytan Kılıçarslan.

Ethics declarations

Ethical Approval

Not applicable.

Conflict of Interests

The results/data/figures in this manuscript have not been published elsewhere. There is no conflict of interest in the article.

Competing Interests

The author has no competing interests to declare that are relevant to the content of this article.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOC 1321 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kılıçarslan, F.A. Synthesis, Spectral, and Fluorescence Studies of Fluorophenyl Methoxy Substituted Nickel Phthalocyanine Complex. J Fluoresc 33, 2461–2467 (2023). https://doi.org/10.1007/s10895-023-03241-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-023-03241-z

Keywords

Navigation