Internally 1,3-phenylene- and 2,5-thienylene-bridged decaphyrins 2 and 3 have been synthesized. While 2 shows modest aromatic character derived from the global 46π-conjugated circuit, 3 displays larger aromatic character owing to the contribution of an (annuleno)annulene-type network consisting of two twisted Möbius aromatic thiahexaphyrin segments in addition to the global 46π-network. Upon protonation, these decaphyrins underwent large structural changes to acquire strong aromaticity. Protonated 3 has been revealed to take on a planar structure composed of fused two triangular thiahexaphyrin segments.
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The work at Kyoto was supported by JSPS KAKENHI Grant Numbers 25220802 and 16K13952. T.S. acknowledges a JSPS Fellowship for Young Scientists. The research at Yonsei University was supported by the Global Research Laboratory (GRL) Program (2013K1A1A2A02050183) of the Ministry of Education, Science and Technology (MEST) of Korea. The quantum calculations of ACID were performed using the supercomputing resources of the Korea Institute of Science and Technology Information (KISTI).
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