First approach to nitrogen-containing fused aromatic hydrocarbons as targets for organoelectronics utilizing a new transformation of O-protected diaryl methanols.
A new concise approach for the construction of heteroatom analogues of polycyclic aromatic benzo[g]quinoline, benzo[b]carbazole, and pyrido[b]carbazole systems via diaryl methanols is described. This transformation involves formation of a central benzene ring fused to two aromatic 5- or 6-membered rings of pyrrole and/or pyridine by using a combination of two aromatic aldehydes, of which at least one contains a ring nitrogen. Analysis of the UV and fluorescent properties, Stokes shifts, quantum yields in solution, and pi-stacking interactions in the crystal structures of the new materials was performed. These polycyclic aromatic compounds show potential as small-molecule organoelectronic materials.
Bałczewski
Piotr
P
Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland. pbalczew@bilbo.cbmm.lodz.pl
Bodzioch
Agnieszka
A
Rózycka-Sokołowska
Ewa
E
Marciniak
Bernard
B
Uznański
Paweł
P
D018360:Crystallography, X-Ray; D003500:Cyclization; D005453:Fluorescence; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D011084:Polycyclic Aromatic Hydrocarbons; D011804:Quinolines; D009584:Nitrogen; D000432:Methanol