Atsuhiro Osuka

First published: 25 May 2012

https://doi.org/10.1002/anie.201203104

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“If I were not a scientist, I would be a painter. The most significant scientific advance of the last 100 years has been the Haber–Bosch process for ammonia synthesis …︁” This and more about Atsuhiro Osuka can be found on page 9970.

References

1“meso,meso-Linked Porphyrin Arrays”: A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93–95;
10.1002/ange.19971090126
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Angew. Chem. Int. Ed. Engl. 1997, 36, 135–137. We found this meso–meso coupling reaction accidentally during the preparation of meso-nitroporphyrin. This reaction has since been widely used for creation of various directly connected porphyrin arrays. Besides this, the reaction is important since it is the first demonstration that the oxidation of metalloporphyrins leads to the formation of directly linked porphyrin dimers and oligomers. On the basis of this reaction, my student N. Aratani synthesized a 1024-mer that has remained the longest discrete man-made molecule reported to date.
10.1002/anie.199701351
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2“Fully Conjugated Porphyrin Tapes with Electronic Absorption Bands That Reach into Infrared”: A. Tsuda, A. Osuka, Science 2001, 293, 79–82. After the finding of meso–meso linked porphyrin oligomers, we dreamed of long meso–meso, β–β, β–β triply linked porphyrin oligomers (porphyrin tapes) because of their beautiful molecular shape and expected highly conjugated nature. In the meantime, my student A. Tsuda invented the oxidation with DDQ/Sc(OTf)₃, hence making our dream come true. The thus-prepared long porphyrin tapes indeed display remarkably red-shifted absorption bands that reach into the infrared.
10.1126/science.1059552
CAS PubMed Web of Science® Google Scholar
3“meso-Aryl-Substituted Expanded Porphyrins”: J.-Y. Shin, H. Furuta, K. Yoza, S. Igarashi, A. Osuka, J. Am. Chem. Soc. 2001, 123, 7190–7191. In the synthesis of tetrakis(pentafluorophenyl)porphyrin by the Lindsey method, my student J.-Y. Shin found that when both reactants were at a concentration of 67 mM, 10 times the excess recommended for porphyrin synthesis, the reaction led to the formation of a series of meso-aryl expanded porphyrins. These compounds possess intriguing structures, reactivities, coordination behavior, and large two-photon absorption cross-sections.
10.1021/ja0106624
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4“Tribenzosubporphines: Synthesis and Characterization”: Y. Inokuma, J. H. Kwon, M.-C. Yoon, D. Kim, A. Osuka, Angew. Chem. 2006, 118, 975–978;
10.1002/ange.200503426
Google Scholar
Angew. Chem. Int. Ed. 2006, 45, 961–964. Subporphyrins are ring-contracted porphyrins consisting of three pyrrole rings and three methine carbon atoms. Despite their simple structures and important position in porphyrin chemistry, they were elusive until our first synthesis. My student Y. Inokuma independently explored the first synthesis of tribenzosubporphines, and confirmed their bowl-shaped structures, 14π-electronic aromaticity, and green fluorescence. This work was followed by the synthesis of meso-aryl-substituted subporphyrins that exhibit variable optical properties depending on the meso-aryl substituents.
10.1002/anie.200503426
CAS PubMed Web of Science® Google Scholar
5“Metalation of Expanded Porphyrins: A Chemical Trigger Used to Produce Molecular Twisting and Möbius Aromaticity”: Y. Tanaka, S. Saito, S. Mori, N. Aratani, H. Shinokubo, N. Shibata, Y. Higuchi, Z. S. Yoon, K. S. Kim, S. B. Noh, J. K. Park, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 693–696;
10.1002/ange.200704407
Web of Science® Google Scholar
Angew. Chem. Int. Ed. 2008, 47, 681–684. Möbius aromaticity was predicted by Heilbronner almost 50 years ago, but its experimental verification had been thought very difficult, since the two conflicting structural elements, namely cyclic conjugation and twisted topology, have to be implemented within a single molecule. Meso-aryl expanded porphyrins have been demonstrated to be an ideal platform to realize Möbius aromatic and antiaromatic molecules. So far, we have synthesized more than 30 Möbius aromatic expanded porphyrins, thus showing that the formation of such porphyrins is not accidental but quite general.
10.1002/anie.200704407
CAS PubMed Web of Science® Google Scholar

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Volume51, Issue40

October 1, 2012

Pages 9970-9971

Atsuhiro Osuka

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