Synthesis of pyrrole-containing polycyclic aromatic hydrocarbons with remarkable curvatures
| Project/Area Number |
26810021
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Organic chemistry
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| Research Institution | Kyoto University |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2015: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 多環芳香族炭化水素 / 酸化的縮環反応 / 芳香族性 / 湾曲化合物 / ピロール / 縮環反応 / 分子ねじれ / 発光特性 / X線結晶構造解析 |
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| Outline of Final Research Achievements |
Tetrabenzotetraaza[8]circulene was obtained by "fold-in" type oxidative fusion reaction of ortho-phenylene bridged cyclic tetrapyrrole in high yield. This planar aromatic molecule exhibited bright blue emission with a quite small Stokes shift. The optical property was tunable by sequential alkylations of the outer-pointing NH groups.
With this new synthetic method in hands, the synthesis of triazasumanene was examined. However, the same oxidative fusion reaction of cyclic tripyrrole furnished partially fused compound in low yield. The same protocol was utilized for cyclic hexapyrrole, which afforded partially fused closed-helicenes in a selective manner. Overall, the "fold-in" type fusion reaction was found to be quite sensitive to the flexibility of the cyclic precursor.
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Report
(4 results)
Research Products
(58 results)
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[Journal Article] β-to-β 2,5-Pyrrolylene-Linked Cyclic Porphyrin Oligomers2016
Author(s)
Y. Rao, J. O. Kim, W. Kim, G. Zhong, B. Yin, M. Zhou, H. Shinokubo, N. Aratani, T. Tanaka, S. Liu, A. Osuka, D. Kim, J. Song
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Journal Title
Chem. Eur. J.
Volume: 52
Issue: 26
Pages: 8801-8804
DOI
Related Report
Peer Reviewed / Int'l Joint Research
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[Journal Article] J. Phys. Chem. A2016
Author(s)
Mori, T.; Tanaka, T.; Higashino, T.; Yoshida, K.; Osuka, A.
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Journal Title
Combined Experimental and Theoretical Investigations on Optical Activities of Mobius Aromatic and Mobius Antiaromatic Hexaphyrin Phosphorus Complexes
Volume: 120
Issue: 24
Pages: 4241-4248
DOI
Related Report
Peer Reviewed / Acknowledgement Compliant
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[Journal Article] Multifaceted [36]octaphyrin (1.1.1.1.1.1.1.1): deprotonationinduced switching among nonaromatic, Möbius aromatic, and Hückel antiaromatic species2016
Author(s)
Won-Young Cha, Takanori Soya, Takayuki Tanaka, Hirotaka Mori, Yongseok Hong, Sangsu Lee, Kyu Hyung Park, Atsuhiro Osuka, and Dongho Kim
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Journal Title
Chemical Communications
Volume: N/A
Issue: 36
Pages: 6076-6078
DOI
Related Report
Peer Reviewed / Int'l Joint Research
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[Journal Article] Triply-linked Corrole Dimers2016
Author(s)
Shota Ooi, Takayuki Tanaka, Kyu Hyung Park, Dongho Kim, and Atsuhiro Osuka
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Journal Title
Angewandte Chemie International Edition
Volume: 55
Issue: 22
Pages: 6535-6539
DOI
Related Report
Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
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