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Preparation and Properties of 2‐(9′‐Carbazolyl)‐3‐(8″‐hydroxy‐2″‐Quinolinyl)Acrylonitrile Derivatives
Author(s) -
Xu PengFei,
Chow Tahsin J.,
Lin Richard,
Lu TaJung
Publication year - 2003
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200300019
Subject(s) - chemistry , quinoline , carbazole , acrylonitrile , dihedral angle , chromophore , alkoxy group , conjugated system , crystallography , photochemistry , luminescence , molecule , double bond , protonation , oled , condensation reaction , polymer chemistry , organic chemistry , hydrogen bond , ion , alkyl , physics , optoelectronics , layer (electronics) , copolymer , catalysis , polymer
The E and Z ‐isomers of the titled compound were synthesized by condensation of 2‐carboxaldehyde‐8‐alkyloxyquinoline and N‐cyanomethylcarbazole, followed by hydrolysis. The alkoxy protection groups in 3b‐c can be cleaved either in acid or in base to yield 3a . All compounds exhibit blue/green luminescence, which may be used as emitting materials in the fabrication of light‐emitting diodes. Crystal diffraction analyses were performed for 3a ‐ E , 3d ‐ Z , and 4 ‐ Z , while the results indicated the presence of a common structural feature among these molecules. The rings of quinoline are co‐planar with the double bond of acrylonitrile, forming a major conjugated chromophore. The carbazole group is twisted along the N(9″)‐C(2) bond away from the major plane with a large dihedral angle. The major conjugated chromphore was found to be responsible for the spectral properties of these compounds. Protonation of the quinoline in these compounds red‐shifted their absorption bands substantially.