Synthesis, Characterization, and Spectroscopic Studies of Bis-(meso-4-methoxyphenyl)-Benziporphyrin and Its Pd-Metal Complex
Benziporphyrin systems are widely explored, yet alternative improved synthetic routes towards these systems are needed. Here, a fairly and efficient synthesis of the free base and its metal complex is well designed. Dimethoxybenzene dicarbinol intermediate was prepared in excellent yields by reactin...
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| Format: | Article |
| Language: | English |
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Wiley
2021-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2021/4586739 |
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| author | Endale Mulugeta Chang-Hee Lee |
| author_facet | Endale Mulugeta Chang-Hee Lee |
| author_sort | Endale Mulugeta |
| collection | DOAJ |
| description | Benziporphyrin systems are widely explored, yet alternative improved synthetic routes towards these systems are needed. Here, a fairly and efficient synthesis of the free base and its metal complex is well designed. Dimethoxybenzene dicarbinol intermediate was prepared in excellent yields by reacting 4-methoxyphenylmagnesium bromide with isophthaladehyde in diethyl ether. Reaction with equivalent pyrrole and pentafluorobenzaldehyde in the presence of trifluoroacetic acid (TFA), followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), provided good yields of bis-(meso-4-methoxyphenyl)-benziporphyrin. Metalation of the free base was performed using palladium(II) acetate salt in acetonitrile. All intermediates and the final products are fully characterized using NMR, HMRS, and UV-Vis spectroscopies and briefly discussed. |
| format | Article |
| id | doaj-art-1e9abf1ac016404ca455df847e6cfa8b |
| institution | Kabale University |
| issn | 2090-9071 |
| language | English |
| publishDate | 2021-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-1e9abf1ac016404ca455df847e6cfa8b2025-02-03T01:20:38ZengWileyJournal of Chemistry2090-90712021-01-01202110.1155/2021/4586739Synthesis, Characterization, and Spectroscopic Studies of Bis-(meso-4-methoxyphenyl)-Benziporphyrin and Its Pd-Metal ComplexEndale Mulugeta0Chang-Hee Lee1Department of Applied ChemistryDepartment ChemistryBenziporphyrin systems are widely explored, yet alternative improved synthetic routes towards these systems are needed. Here, a fairly and efficient synthesis of the free base and its metal complex is well designed. Dimethoxybenzene dicarbinol intermediate was prepared in excellent yields by reacting 4-methoxyphenylmagnesium bromide with isophthaladehyde in diethyl ether. Reaction with equivalent pyrrole and pentafluorobenzaldehyde in the presence of trifluoroacetic acid (TFA), followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), provided good yields of bis-(meso-4-methoxyphenyl)-benziporphyrin. Metalation of the free base was performed using palladium(II) acetate salt in acetonitrile. All intermediates and the final products are fully characterized using NMR, HMRS, and UV-Vis spectroscopies and briefly discussed.http://dx.doi.org/10.1155/2021/4586739 |
| spellingShingle | Endale Mulugeta Chang-Hee Lee Synthesis, Characterization, and Spectroscopic Studies of Bis-(meso-4-methoxyphenyl)-Benziporphyrin and Its Pd-Metal Complex Journal of Chemistry |
| title | Synthesis, Characterization, and Spectroscopic Studies of Bis-(meso-4-methoxyphenyl)-Benziporphyrin and Its Pd-Metal Complex |
| title_full | Synthesis, Characterization, and Spectroscopic Studies of Bis-(meso-4-methoxyphenyl)-Benziporphyrin and Its Pd-Metal Complex |
| title_fullStr | Synthesis, Characterization, and Spectroscopic Studies of Bis-(meso-4-methoxyphenyl)-Benziporphyrin and Its Pd-Metal Complex |
| title_full_unstemmed | Synthesis, Characterization, and Spectroscopic Studies of Bis-(meso-4-methoxyphenyl)-Benziporphyrin and Its Pd-Metal Complex |
| title_short | Synthesis, Characterization, and Spectroscopic Studies of Bis-(meso-4-methoxyphenyl)-Benziporphyrin and Its Pd-Metal Complex |
| title_sort | synthesis characterization and spectroscopic studies of bis meso 4 methoxyphenyl benziporphyrin and its pd metal complex |
| url | http://dx.doi.org/10.1155/2021/4586739 |
| work_keys_str_mv | AT endalemulugeta synthesischaracterizationandspectroscopicstudiesofbismeso4methoxyphenylbenziporphyrinanditspdmetalcomplex AT changheelee synthesischaracterizationandspectroscopicstudiesofbismeso4methoxyphenylbenziporphyrinanditspdmetalcomplex |