Revisiting Fused‐Pyrrolo‐1,10‐Phenanthroline Derivatives: Novel Transformations and Stability Studies
In this study, new pyrrolo[3',4':3,4]pyrrolo[1,2‐a][1,10]phenanthroline derivatives are developed and their stabilities and transformation pathways are investigated. The synthetic approach toward these novel derivatives include a pivotal [3 + 2] cycloaddition of in situ generated ylides, f...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2025-07-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.202400365 |
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| author | Cristina M. Al Matarneh Alina Nicolescu Sergiu Shova Mircea Apostu Razvan Puf Francesca Mocci Aatto Laaksonen Ionel I. Mangalagiu Ramona Danac |
| author_facet | Cristina M. Al Matarneh Alina Nicolescu Sergiu Shova Mircea Apostu Razvan Puf Francesca Mocci Aatto Laaksonen Ionel I. Mangalagiu Ramona Danac |
| author_sort | Cristina M. Al Matarneh |
| collection | DOAJ |
| description | In this study, new pyrrolo[3',4':3,4]pyrrolo[1,2‐a][1,10]phenanthroline derivatives are developed and their stabilities and transformation pathways are investigated. The synthetic approach toward these novel derivatives include a pivotal [3 + 2] cycloaddition of in situ generated ylides, followed by cycloadducts oxidation and other unexpected transformations. The structures of the intermediate and final compounds are proposed based on information obtained from several spectral techniques. Stability study reveal that electron‐donating groups in the para position of the phenyl ring promote easier oxidation, whereas electron‐withdrawing substituents enhance the stability of the compounds. The acid–base titration of α‐monosubstituted 1,10‐phenanthroline 6a results in a reversible color change, which is preliminarily explored through spectral methods. |
| format | Article |
| id | doaj-art-2cb31acaccf04759944bf52d7ed1da55 |
| institution | DOAJ |
| issn | 2191-1363 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj-art-2cb31acaccf04759944bf52d7ed1da552025-08-20T03:12:26ZengWiley-VCHChemistryOpen2191-13632025-07-01147n/an/a10.1002/open.202400365Revisiting Fused‐Pyrrolo‐1,10‐Phenanthroline Derivatives: Novel Transformations and Stability StudiesCristina M. Al Matarneh0Alina Nicolescu1Sergiu Shova2Mircea Apostu3Razvan Puf4Francesca Mocci5Aatto Laaksonen6Ionel I. Mangalagiu7Ramona Danac8Center of Advanced Research in Bionanoconjugates and Biopolymers “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy 41A Grigore Ghica Voda Alley Iasi 700487 RomaniaNMR Laboratory “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy 41A Grigore Ghica Voda Alley Iasi 700487 RomaniaDepartment of Inorganic Polymers “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy 41A Grigore Ghica Voda Alley Iasi 700487 RomaniaFaculty of Chemistry “Alexandru Ioan Cuza” University of Iasi 11 Carol I Iasi 700506 RomaniaCenter of Advanced Research in Bionanoconjugates and Biopolymers “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy 41A Grigore Ghica Voda Alley Iasi 700487 RomaniaDepartment of Chemical and Geological Sciences University of Cagliari Cagliari 09124 ItalyCenter of Advanced Research in Bionanoconjugates and Biopolymers “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy 41A Grigore Ghica Voda Alley Iasi 700487 RomaniaFaculty of Chemistry “Alexandru Ioan Cuza” University of Iasi 11 Carol I Iasi 700506 RomaniaFaculty of Chemistry “Alexandru Ioan Cuza” University of Iasi 11 Carol I Iasi 700506 RomaniaIn this study, new pyrrolo[3',4':3,4]pyrrolo[1,2‐a][1,10]phenanthroline derivatives are developed and their stabilities and transformation pathways are investigated. The synthetic approach toward these novel derivatives include a pivotal [3 + 2] cycloaddition of in situ generated ylides, followed by cycloadducts oxidation and other unexpected transformations. The structures of the intermediate and final compounds are proposed based on information obtained from several spectral techniques. Stability study reveal that electron‐donating groups in the para position of the phenyl ring promote easier oxidation, whereas electron‐withdrawing substituents enhance the stability of the compounds. The acid–base titration of α‐monosubstituted 1,10‐phenanthroline 6a results in a reversible color change, which is preliminarily explored through spectral methods.https://doi.org/10.1002/open.2024003651,10‐phenanthrolineconformational studiesDFT calculationsNMR spectroscopy |
| spellingShingle | Cristina M. Al Matarneh Alina Nicolescu Sergiu Shova Mircea Apostu Razvan Puf Francesca Mocci Aatto Laaksonen Ionel I. Mangalagiu Ramona Danac Revisiting Fused‐Pyrrolo‐1,10‐Phenanthroline Derivatives: Novel Transformations and Stability Studies ChemistryOpen 1,10‐phenanthroline conformational studies DFT calculations NMR spectroscopy |
| title | Revisiting Fused‐Pyrrolo‐1,10‐Phenanthroline Derivatives: Novel Transformations and Stability Studies |
| title_full | Revisiting Fused‐Pyrrolo‐1,10‐Phenanthroline Derivatives: Novel Transformations and Stability Studies |
| title_fullStr | Revisiting Fused‐Pyrrolo‐1,10‐Phenanthroline Derivatives: Novel Transformations and Stability Studies |
| title_full_unstemmed | Revisiting Fused‐Pyrrolo‐1,10‐Phenanthroline Derivatives: Novel Transformations and Stability Studies |
| title_short | Revisiting Fused‐Pyrrolo‐1,10‐Phenanthroline Derivatives: Novel Transformations and Stability Studies |
| title_sort | revisiting fused pyrrolo 1 10 phenanthroline derivatives novel transformations and stability studies |
| topic | 1,10‐phenanthroline conformational studies DFT calculations NMR spectroscopy |
| url | https://doi.org/10.1002/open.202400365 |
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