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First Approach to Nitrogen‐Containing Fused Aromatic Hydrocarbons as Targets for Organoelectronics Utilizing a New Transformation of O ‐Protected Diaryl Methanols
Author(s) -
Bałczewski Piotr,
Bodzioch Agnieszka,
RóżyckaSokołowska Ewa,
Marciniak Bernard,
Uznański Paweł
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901947
Subject(s) - carbazole , pyrrole , chemistry , ring (chemistry) , pyridine , aromaticity , heteroatom , quinoline , benzene , stacking , molecule , polycyclic aromatic hydrocarbon , isoquinoline , nitrogen , nitration , thiophene , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry
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 π‐stacking interactions in the crystal structures of the new materials was performed. These polycyclic aromatic compounds show potential as small‐molecule organoelectronic materials.