Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups
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 synthesize...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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BMC
2017-04-01
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| Series: | Chemistry Central Journal |
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| Online Access: | http://link.springer.com/article/10.1186/s13065-017-0260-x |
| _version_ | 1818583296515244032 |
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| author | Jiří Černý Lenka Dokládalová Petra Horáková Antonín Lyčka Tomáš Mikysek Filip Bureš |
| author_facet | Jiří Černý Lenka Dokládalová Petra Horáková Antonín Lyčka Tomáš Mikysek Filip Bureš |
| author_sort | Jiří Černý |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-16T08:03:02Z |
| format | Article |
| id | doaj.art-9793968a9c2e4389a227c00d47780646 |
| institution | Directory Open Access Journal |
| issn | 1752-153X |
| language | English |
| last_indexed | 2024-12-16T08:03:02Z |
| publishDate | 2017-04-01 |
| publisher | BMC |
| record_format | Article |
| series | Chemistry Central Journal |
| spelling | doaj.art-9793968a9c2e4389a227c00d477806462022-12-21T22:38:34ZengBMCChemistry Central Journal1752-153X2017-04-011111910.1186/s13065-017-0260-xPreparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groupsJiří Černý0Lenka Dokládalová1Petra Horáková2Antonín Lyčka3Tomáš Mikysek4Filip Bureš5Centre of Organic Chemistry Ltd.Centre of Organic Chemistry Ltd.Centre of Organic Chemistry Ltd.Centre of Organic Chemistry Ltd.Department of Analytical Chemistry, University of Pardubice, Faculty of Chemical TechnologyInstitute of Organic Chemistry and Technology, University of Pardubice, Faculty of Chemical TechnologyAbstract 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.http://link.springer.com/article/10.1186/s13065-017-0260-xRare-earth bisphthalocyaninesUV–vis spectroscopyNIR spectroscopySinglet oxygen productionReductionCyclic voltammetry |
| spellingShingle | Jiří Černý Lenka Dokládalová Petra Horáková Antonín Lyčka Tomáš Mikysek Filip Bureš Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups Chemistry Central Journal Rare-earth bisphthalocyanines UV–vis spectroscopy NIR spectroscopy Singlet oxygen production Reduction Cyclic voltammetry |
| title | Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups |
| title_full | Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups |
| title_fullStr | Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups |
| title_full_unstemmed | Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups |
| title_short | Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups |
| title_sort | preparation and characterization of novel double decker rare earth phthalocyanines substituted with 5 bromo 2 thienyl groups |
| topic | Rare-earth bisphthalocyanines UV–vis spectroscopy NIR spectroscopy Singlet oxygen production Reduction Cyclic voltammetry |
| url | http://link.springer.com/article/10.1186/s13065-017-0260-x |
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