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Molecules 2017, 22(6), 908; doi:10.3390/molecules22060908

Synthesis, Characterization and Protonation Behavior of Quinoxaline-Fused Porphycenes

Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama-cho, Ikoma 630-0192, Japan
Current address: Faculty of Science and Engineering, Iwate University, 4-3-5 Ueda, Morioka 020-8551, Japan.
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Academic Editor: Derek J. McPhee
Received: 13 April 2017 / Revised: 15 May 2017 / Accepted: 24 May 2017 / Published: 31 May 2017
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Abstract

9,10-Quinoxaline-fused porphycenes 1a-H2 and 1b-H2 were synthesized by intramolecular McMurry coupling. As a result of the annulation of the quinoxaline moiety on the porphycene skeleton, 1a-H2 and 1b-H2 display absorption and fluorescence in the near infra-red (NIR) region. Additionally, the quinoxaline moieties of 1a-H2 and 1b-H2 act as electron-withdrawing groups, introducing lower reduction potentials than for pristine porphycene. The protonation occurred at the nitrogen atoms in the cavity of freebase porphycenes and at the quinoxaline moieties for their nickel complexes to give diprotonic species. View Full-Text
Keywords: porphycene; π-expansion; NIR absorption and fluorescence; protonation porphycene; π-expansion; NIR absorption and fluorescence; protonation
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Kuzuhara, D.; Sakaguchi, M.; Furukawa, W.; Okabe, T.; Aratani, N.; Yamada, H. Synthesis, Characterization and Protonation Behavior of Quinoxaline-Fused Porphycenes. Molecules 2017, 22, 908.

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