1986 Fiscal Year Final Research Report Summary
Reseach of New Heterocycles: Pyrrolo-pyrrole and Azapentalene.
| Project/Area Number |
60470021
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | TOHOKU UNIVERSITY |
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Principal Investigator |
MUKAI Toshio Department of Chemistry, Tohoku University (Professor), 理学部, 教授 (30004237)
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| Co-Investigator(Kenkyū-buntansha) |
TERUI Yoriko Photochemical Research Laboratory, Tohoku University, 理学部, 助手 (00197815)
KUMAGAI Tsutomu Department of Chemistry, Tohoku University, 理学部, 助手 (60091683)
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| Project Period (FY) |
1985 – 1986
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| Keywords | Heteroaromaticity / Pyrrole / Electron-Donating Ability / Ionization Potential / Conductive Polymer Firm / Heterocyclic Compound / Pentalene / 反芳香族性 |
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| Research Abstract |
Physical and chemical properties of 1,4-dihydropyrrolo[3,2-b]pyrroles synthesized in this project were systematically investigated. In addition to the X-ray analysis, the NMR spectra indicated that dihydropyrrolo[3,2-b]pyrrole was a typical heteroaromatic compound possessing planar 10 <pi> electron system. The electronic structure was also elucidated by means of He(I) photoelectron spectroscopy combined with molecular orbital calculations. The extraordinarily electron-donating ability was corresponded to the lower ionization potential (7.27 eV), oxidation potential (0.51 V), and the degree of basicity (pKa= 3.6) as well as the reactivity with electrophilic reagents. The electro-oxidation of this system afforded a conductive polymer firm. The physical, electrochemical, electrical, and spectroscopic properties were compared with those of polypyrrole and polyacetylene. 3,6-Di-t-butyl-1,4-diazapentalene was successfully synthesized and the antiaromatic character was discribed on the basis of spectral data and molecular orbital consideration. In addition, some interesting chemical properties of the related heterocycle, 2,8-diazabicyclo[3.2.1]octadiene, were uncovered.
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