Studies on Pyrene and Perylene Derivatives upon Oxidation and Application to a Higher Analogue
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Abstract
The structure and electronic features of neutral and positively charged pyrene and perylene derivatives were explored. The radical cation of 1,3,6,8-tetraarylpyrene 1 was examined by ESR, UV-vis-NIR spectroscopy and theoretical calculations. The addition of 2 equiv of oxidant to 1 resulted in the formation of dication 12+. The single-crystal X-ray structure of 12+ proved that the aromatic part relocates from biphenyl unit to naphthyl unit upon 2e- oxidation of 1. We have also investigated the oxidation processes of 3,9-diarylperylene 2 and 3,10-diarylperylene 3. The radical cations of 2・+ and 3・+ showed ESR signals and the spin densities were proven to delocalize at 3,4,9,10-positions. In the case of doubly charged 3,9-diarylperylene, we could find the anthracene structure in the core, while the phenanthrene skeleton appeared in two-electron oxidized 3,10-diarylperylene. Finally we validated this phenomenon to apply for the higher analogue terrylene, discovering its large aromaticity relocation upon the 2e- oxidation.
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 90 (6), 667-677, 2017-03-09
The Chemical Society of Japan
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Details 詳細情報について
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- CRID
- 1050295834375982208
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- NII Article ID
- 130006770647
- 120006395245
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- NII Book ID
- AA00580132
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- ISSN
- 00092673
- 13480634
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- HANDLE
- 10061/12196
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- NDL BIB ID
- 028285578
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- Text Lang
- en
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- Article Type
- journal article
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- Data Source
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- IRDB
- NDL
- Crossref
- CiNii Articles
- KAKEN