Events & Seminars > Event Details


4:00 pm
Room 304, Chemistry Building

Straightforward Approach to Novel Curved-π Molecules: Synthesis, Structures and Applications


Professor Satoru Hiroto
Nagoya University

Hosted by: Professor Cassandra Fraser

π-Conjugated molecules with three-dimensional architectures have attracted broad interest. In addition to their structural beauty, they exhibit unique characteristics arising from their distorted π-surface. Recently, we discovered that oxidation of amino-substituted porphyrins proceeded with high regioselectivity to afford the pyrazine-fused dimers in a one-pot operation.1 Applying this protocol to aminoanthracenes, azahelicenes were readily obtained in high yield.2 In addition, meso-tetraarylporphyrins were converted into the pyrazine-fused dimers in the same manner. X-ray diffraction analysis showed that all dimers were highly twisted. The twisted porphyrin dimer was further extended to the tetramer through an amination and oxidation sequence. The structure unveiled by X-ray diffraction analysis exhibited a unidirectionally twisting conformation with the largest twisting angle ever reported (ca. 300°).3 We also achieved the first efficient synthesis of a nitrogen-embedded buckybowl.4 Given that all of these processes have been conducted under mild conditions, these curved-π molecules could be novel building blocks for supramolecular and polymeric materials.

Satoru Hiroto was born in Shimane Prefecture, Japan. He received his B.S. in Science at Kyoto University in 2004, where he performed undergraduate research in organic synthesis related to porphyrin chemistry with Prof. Atsuhiro Osuka. Dr. Hiroto then entered the Graduate School of Science at Kyoto University and worked with Profs. Atsuhiro Osuka and Hiroshi Shinokubo to develop organometal-catalyzed functionalization of porphyrin derivatives. He received his Ph.D. in Science from Kyoto University in 2009. During doctorial study, Dr. Hiroto was a research fellow of the Japan Society for the Promotion of Science (JSPS) for two years. Dr. Hiroto started his professional career at Nagoya University as an Assistant Professor in 2009. At Nagoya University, Dr. Hiroto’s work involves organic synthesis for molecular devices, developing synthetic methodology of distorted π-conjugated molecules, dyes with chiroptical and electron-conducting properties.