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Wu TL, Chou HH, Huang PY, et al. 3,6,9,12-Tetrasubstituted chrysenes: synthesis, photophysical properties, and application as blue fluorescent OLED. J Org Chem. 2013;79(1):267-74doi: 10.1021/jo402429q.
Wu, T. L., Chou, H. H., Huang, P. Y., Cheng, C. H., & Liu, R. S. (2014). 3,6,9,12-Tetrasubstituted chrysenes: synthesis, photophysical properties, and application as blue fluorescent OLED. The Journal of organic chemistry, 79(1), 267-74. https://doi.org/10.1021/jo402429q
Wu, Tien-Lin, et al. "3,6,9,12-Tetrasubstituted chrysenes: synthesis, photophysical properties, and application as blue fluorescent OLED." The Journal of organic chemistry vol. 79,1 (2014): 267-74. doi: https://doi.org/10.1021/jo402429q
Wu TL, Chou HH, Huang PY, Cheng CH, Liu RS. 3,6,9,12-Tetrasubstituted chrysenes: synthesis, photophysical properties, and application as blue fluorescent OLED. J Org Chem. 2014 Jan 03;79(1):267-74. doi: 10.1021/jo402429q. Epub 2013 Dec 05. PMID: 24295385.
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J Org Chem. 2014 Jan 03;79(1):267-74. doi: 10.1021/jo402429q. Epub 2013 Dec 05.

3,6,9,12-Tetrasubstituted chrysenes: synthesis, photophysical properties, and application as blue fluorescent OLED.

The Journal of organic chemistry

Tien-Lin Wu, Ho-Hsiu Chou, Pei-Yun Huang, Chien-Hong Cheng, Rai-Shung Liu

Affiliations

  1. Department of Chemistry, National Tsing Hua University , Hsinchu, Taiwan, ROC.

PMID: 24295385 DOI: 10.1021/jo402429q

Abstract

A short synthesis of unsubstituted chrysene is described to provide a cheap source of this compound. This chrysene was used to prepare 3,6,9,12-tetrabromochrysene, which was subsequently transformed into various 3,6,9,12-tetrasubstituted chrysenes bearing four aryl, alkynyl, or amino groups by means of the Suzuki, Sonogashira, or Buchwald-Hartwig coupling reaction, respectively. These substituents result in large bathochromic shifts in the chrysene absorption and emission spectra. These new chrysene derivatives show blue fluorescent emission (401-471 nm) with high quantum yields (0.44-0.87). DFT calculations on these chrysenes rationalize well the substituent effects on their HOMO and LUMO energy levels. One representative chrysene (6g) was used as a blue fluorescent emitter in an OLED device that showed an outstanding external quantum efficiency (η = 6.31%) with blue emission [CIE (x, y) = (0.13, 0.20)] and a low turn-on voltage (3.0 V).

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