Al Matarneh Cristina M, Nicolescu Alina, Shova Sergiu, Apostu Mircea, Puf Razvan, Mocci Francesca, Laaksonen Aatto, Mangalagiu Ionel I, Danac Ramona
Center of Advanced Research in Bionanoconjugates and Biopolymers, "Petru Poni" Institute of Macromolecular Chemistry of Romanian Academy, 41A Grigore Ghica Voda Alley, Iasi, 700487, Romania.
NMR Laboratory, "Petru Poni" Institute of Macromolecular Chemistry of Romanian Academy, 41A Grigore Ghica Voda Alley, Iasi, 700487, Romania.
ChemistryOpen. 2025 Jul;14(7):e202400365. doi: 10.1002/open.202400365. Epub 2025 May 6.
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.
在本研究中，开发了新型吡咯并[3',4':3,4]吡咯并[1,2 - a][1,10]菲咯啉衍生物，并研究了它们的稳定性和转化途径。合成这些新型衍生物的方法包括原位生成叶立德的关键[3 + 2]环加成反应，随后是环加成产物的氧化和其他意外转化。基于从几种光谱技术获得的信息，提出了中间体和最终化合物的结构。稳定性研究表明，苯环对位的供电子基团促进更容易的氧化，而吸电子取代基增强了化合物的稳定性。α-单取代1,10 - 菲咯啉6a的酸碱滴定导致可逆的颜色变化，通过光谱方法对其进行了初步探索。
