Spectral-Fluorescence Properties of Zn(II)-Octaphenyltetraazaporphyrins

Zn(II)-octa-(4-chlorophenyl)- and Zn(II)-octa-(4-bromophenyl)tetraazaporphyrins were synthesized by the reaction of cyclotetramerization of di-(4-chlorophenyl)- and di-(4-bromophenyl)maleonitriles with zinc(II) chloride. The obtained compounds were identified by UV-vis, IR, NMR 1 H spectroscopy and...

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Bibliographic Details
Published in:Journal of fluorescence 2020-05, Vol.30 (3), p.657-664
Main Authors: Dmitrieva, Olga A., Chizhova, Natalya V., Rusanov, Alexey I., Koifman, Mikhail O., Mamardashvili, Nugzar Z.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Biochemistry
Biological and Medical Physics
Biomedical and Life Sciences
Biomedicine
Biophysics
Biotechnology
Chemical synthesis
Energy gap
Fluorescence
Infrared spectroscopy
Mass spectrometry
Molecular orbitals
NMR
Nuclear magnetic resonance
Optimization
Original Article
Toluene
Zinc
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Summary:Zn(II)-octa-(4-chlorophenyl)- and Zn(II)-octa-(4-bromophenyl)tetraazaporphyrins were synthesized by the reaction of cyclotetramerization of di-(4-chlorophenyl)- and di-(4-bromophenyl)maleonitriles with zinc(II) chloride. The obtained compounds were identified by UV-vis, IR, NMR 1 H spectroscopy and mass spectrometry. Geometry optimization of the series of halogenated Zn(II)-octaaryltetraazaporphyrins was performed using the density functional method with the BP86 functional and the def2-TZVP basis set. An analysis of the distribution of molecular orbital energies in the neighborhood of highest occupied molecular orbitals (HOMO and HOMO-1) and lowest unoccupied molecular orbitals (LUMO and LUMO+1) and the width of the HOMO – LUMO energy gaps (E H-L ) was performed for the studied compounds. Fluorimetric measurements of the Zn(II)-octaphenyltetraazaporphyrins in toluene were carried out and fluorescence quantum yields of studied compounds were determined and analyzed. It has been shown that the halogen on the para-position of the phenyl groups significantly affects the value of the obtained quantum yields of fluorescence emission but does not significantly affect the Stokes shifts.
ISSN:1053-0509
1573-4994
DOI:10.1007/s10895-020-02530-1