Synthesis, Crystal Structure and Photoluminescent Properties of Novel 9-Cyano-Pyrrolo[1,2-a][1,10]Phenanthrolines

• Published in: Crystals (Basel) 2024-01, Vol.14 (1), p.67
• Main Authors: Cristea, Mihaela, Răducă, Mihai, Shova, Sergiu, Drăghici, Constantin, Neacșu, Vlad A., Maganu, Maria, Albotă (Barbu), Loredana, Dumitrescu, Denisa, Dumitrascu, Florea
• Format: Article
• Language: English
• Subjects: 1,10-phenanthrolinium N-ylide; 1,3-dipolar cycloaddition; Bromides; Chemical bonds; Chemical properties; Chemical research; Crystal structure; Crystals; Experiments; helical chirality; Heterocyclic aromatic compounds; Hydrogen bonds; Molecular structure; Optical properties; Oxidizing agents; Photoluminescence; Production processes; pyrrolo[1,2-a][1,10]phenanthrolines; Single crystals; Software; Spectrophotometry; Structural analysis; Structure; Triethylamine; X-ray diffraction
• ISSN: 2073-4352; 2073-4352
• DOI: 10.3390/cryst14010067

Novel 9-cyano-pyrrolo[1,2-a][1,10]phenanthrolines 6a–d were obtained by an efficient one-pot regioselective reaction between 1,10-phenanthrolinium bromides 2a–d and acrylonitrile as a dipolarophile, in the presence of triethylamine and tetrakis-pyridino-cobalt(II) dichromate (TPCD) as oxidizing agents. The optical properties of the compounds were investigated through UV–Vis spectrophotometry and steady-state photoluminescence measurements, while their structures were elucidated by single-crystal X-ray diffraction. The structural characterization revealed that the molecular structures of the four compounds were stabilized by hydrogen bonds and π–π interactions.