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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/3368
Title: Synthesis, spectra, and theoretical investigations of the triarylamines based on 6 H -indolo[2,3- b ]quinoxaline
Authors: Thomas K.R.J.
Tyagi P.
Published in: Journal of Organic Chemistry
Abstract: Triarylamines containing a 6H-indolo[2,3-b]quinoxaline core and aromatic units such as phenyl, naphthyl, pyrene, anthracene, or fluorene have been synthesized by employing palladium-catalyzed C-N and C-C coupling reactions and characterized by optical absorption and emission spectra, electrochemical behavior, and thermal studies. Even though the electronic absorption spectra of the compounds were influenced by the nature of the peripheral amines, the emission spectra indicated close similarity for the excited states in these compounds. For the derivatives in which the amines were directly anchored on the 6H-indolo[2,3-b]quinoxaline nucleus, the emission appeared to be dominated by the state localized on the 6H-indolo[2,3-b]quinoxaline chromophore, while in the compounds containing the extended conjugation the fluorescence originated from the polyaromatic linker. The compounds displayed green or yellow emission depending on the nature of the amine segment. All of the dyes displayed one-electron quasi-reversible oxidation couple in the cyclic voltammograms, which is attributable to the oxidation of the peripheral amines at the 6H-indolo[2,3-b]quinoxaline core. An additional one-electron oxidation process observable at the high positive potentials for the compounds 7 and 8 probably arises from the oxidation of the arylthiophene segment. The enhanced thermal stability and relatively higher glass transition temperatures observed for these compounds were attributed to the presence of dipolar 6H-indolo[2,3-b] quinoxaline segment. The origin of the optical spectra and the trends observed therein were rationalized using TDDFT simulations. © 2010 American Chemical Society.
Citation: Journal of Organic Chemistry (2010), 75(23): 8100-8111
URI: https://doi.org/10.1021/jo1016663
http://repository.iitr.ac.in/handle/123456789/3368
Issue Date: 2010
ISSN: 223263
Author Scopus IDs: 57203389297
26649189600
Author Affiliations: Thomas, K.R.J., Organic Materials Lab, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India
Tyagi, P., Organic Materials Lab, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India
Corresponding Author: Thomas, K. R. J.; Organic Materials Lab, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India; email: krjt8fcy@iitr.ernet.in
Appears in Collections:Journal Publications [CY]

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