Changes in macrocyclic aromaticity and formation of a charge-separated state by complexation of expanded porphyrin and C60

Won-Young Cha; Ahreum Ahn; Taeyeon Kim; Juwon Oh; Rashid Ali; Jung Su Park; Dongho Kim

doi:10.1039/c9cc03928g

Changes in macrocyclic aromaticity and formation of a charge-separated state by complexation of expanded porphyrin and C60

Chem Commun (Camb). 2019 Jul 11;55(57):8301-8304. doi: 10.1039/c9cc03928g.

Authors

Won-Young Cha¹, Ahreum Ahn², Taeyeon Kim³, Juwon Oh³, Rashid Ali⁴, Jung Su Park⁴, Dongho Kim³

Affiliations

¹ Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University, Seoul 03722, Korea. dongho@yonsei.ac.kr and Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
² Center for Supercomputing Applications, Korea Institute of Science and Technology Information, 245 Daehak-ro, Daejeon 34141, Korea.
³ Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University, Seoul 03722, Korea. dongho@yonsei.ac.kr.
⁴ Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University, Seoul 03722, Korea.

PMID: 31250853
DOI: 10.1039/c9cc03928g

Abstract

Significant changes of macrocyclic aromaticity in expanded porphyrins through C60 complexation were studied by 1H NMR spectroscopy and nucleus-independent chemical shift calculations. This work is a detailed research study of how the formation of a complex of dual aromatic expanded porphyrin with fullerene affects the electron densities in the main conjugation pathways and meso-substituents. Furthermore, we found that the formation of the photoinduced charge-separated state and the triplet excited-state populations of the bowl-shaped and rigid expanded porphyrin can be controlled by a simple complexation with C60.