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Kato S, Yamada Y, Hiyoshi H, et al. Series of Carbazole-Pyrimidine Conjugates: Syntheses and Electronic, Photophysical, and Electrochemical Properties. J Org Chem. 2015;80(18):9076-90doi: 10.1021/acs.joc.5b01409.
Kato, S., Yamada, Y., Hiyoshi, H., Umezu, K., & Nakamura, Y. (2015). Series of Carbazole-Pyrimidine Conjugates: Syntheses and Electronic, Photophysical, and Electrochemical Properties. The Journal of organic chemistry, 80(18), 9076-90. https://doi.org/10.1021/acs.joc.5b01409
Kato, Shin-ichiro, et al. "Series of Carbazole-Pyrimidine Conjugates: Syntheses and Electronic, Photophysical, and Electrochemical Properties." The Journal of organic chemistry vol. 80,18 (2015): 9076-90. doi: https://doi.org/10.1021/acs.joc.5b01409
Kato S, Yamada Y, Hiyoshi H, Umezu K, Nakamura Y. Series of Carbazole-Pyrimidine Conjugates: Syntheses and Electronic, Photophysical, and Electrochemical Properties. J Org Chem. 2015 Sep 18;80(18):9076-90. doi: 10.1021/acs.joc.5b01409. Epub 2015 Aug 28. PMID: 26301629.
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J Org Chem. 2015 Sep 18;80(18):9076-90. doi: 10.1021/acs.joc.5b01409. Epub 2015 Aug 28.

Series of Carbazole-Pyrimidine Conjugates: Syntheses and Electronic, Photophysical, and Electrochemical Properties.

The Journal of organic chemistry

Shin-ichiro Kato, Yuji Yamada, Hidetaka Hiyoshi, Kazuto Umezu, Yosuke Nakamura

Affiliations

  1. Division of Molecular Science, Faculty of Science and Technology, Gunma University , 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.
  2. Ihara Chemical Industry Co., Ltd. , Taito-ku, Tokyo 110-0008, Japan.

PMID: 26301629 DOI: 10.1021/acs.joc.5b01409

Abstract

A series of carbazole-pyrimidine conjugates 1-17 were synthesized by Pd-catalyzed cross-coupling, oxidation, and nucleophilic aromatic substitution reactions. In 1-17, the carbazole moieties are connected at the 4,6-positions of the pyrimidine ring either directly or via ethynylene or vinylene spacers, and various electron-donating or electron-withdrawing substituents are introduced at the 2-position of the pyrimidine ring. The effects of structural variations on the electronic, photophysical, and electrochemical properties of 1-17 were comprehensively investigated. Compounds 1-17 exhibit intramolecular charge-transfer (ICT) states, which essentially lead to moderate-to-strong fluorescence emission with large Stokes shifts depending on the solvent polarity. These compounds tend to show significant changes in optical and fluorescence properties upon addition of trifluoroacetic acid. The electron-accepting ability of these compounds can be tuned by both substituents on the pyrimidine moiety and spacers. The ethynylene spacer lowers both the HOMO and LUMO levels, while the vinylene spacer elevates the HOMO level and lowers the LUMO level. The X-ray crystal structures of 3, 6, 11, and 14 are also disclosed.

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