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Černý J, Dokládalová L, Horáková P, et al. Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups. Chem Cent J. 2017;11(1):31doi: 10.1186/s13065-017-0260-x.
Černý, J., Dokládalová, L., Horáková, P., Lyčka, A., Mikysek, T., & Bureš, F. (2017). Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups. Chemistry Central journal, 11(1), 31. https://doi.org/10.1186/s13065-017-0260-x
Černý, Jiří, et al. "Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups." Chemistry Central journal vol. 11,1 (2017): 31. doi: https://doi.org/10.1186/s13065-017-0260-x
Černý J, Dokládalová L, Horáková P, Lyčka A, Mikysek T, Bureš F. Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups. Chem Cent J. 2017 Apr 05;11(1):31. doi: 10.1186/s13065-017-0260-x. PMID: 29086832; PMCID: PMC5382118.
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Chem Cent J. 2017 Apr 05;11(1):31. doi: 10.1186/s13065-017-0260-x.

Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups.

Chemistry Central journal

Jiří Černý, Lenka Dokládalová, Petra Horáková, Antonín Lyčka, Tomáš Mikysek, Filip Bureš

Affiliations

  1. Centre of Organic Chemistry Ltd., Rybitví 296, 53354, Rybitví, Czech Republic. [email protected].
  2. Centre of Organic Chemistry Ltd., Rybitví 296, 53354, Rybitví, Czech Republic.
  3. Department of Analytical Chemistry, University of Pardubice, Faculty of Chemical Technology, Studentská 573, 53210, Pardubice, Czech Republic.
  4. Institute of Organic Chemistry and Technology, University of Pardubice, Faculty of Chemical Technology, Studentská 573, 53210, Pardubice, Czech Republic.

PMID: 29086832 PMCID: PMC5382118 DOI: 10.1186/s13065-017-0260-x

Abstract

BACKGROUND: A series of rare-earth bisphthalocyanines of praseodymium, samarium and gadolinium bearing 5-bromo-2-thienyl substituents were prepared for the first time.

RESULTS: Three bis[octakis(5-bromo-2-thienyl)] rare-earth metal(III) bisphthalocyanine complexes (Pr, Sm, Gd) were synthesized for the first time. The new compounds were characterized by UV-vis, NIR, FT-IR, mass spectroscopy and thermogravimetry as well as elementary analysis and electrochemistry. Production of singlet oxygen was also estimated using 9,10-dimethylanthracene method.

CONCLUSIONS: The bromine substituent causes significant changes in molecule paramagnetism, singlet oxygen production, HOMO position and spectral characteristics. The compounds in solutions exist in two forms (neutral and/or reduced) depending on the solvent and rare-earth metal. Moreover, the compounds exhibit much increased stability under acid conditions compared with non-brominated derivatives. Graphical abstract Prepared compounds for the study of their chemical and other properties.

Keywords: Acid stability; Cyclic voltammetry; NIR spectroscopy; Rare-earth bisphthalocyanines; Reduction; Singlet oxygen production; Thermogravimetry; UV–vis spectroscopy

References

  1. Inorg Chem. 2001 Aug 27;40(18):4793-7 - PubMed
  2. J Am Chem Soc. 2003 Jul 23;125(29):8694-5 - PubMed
  3. Phys Chem Chem Phys. 2009 Jul 21;11(27):5598-607 - PubMed
  4. Inorg Chem. 2014 May 5;53(9):4359-70 - PubMed

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