Meso-Triaryl-Substituted Smaragdyrins: Facile Aromaticity Switching

Daguan Xie, Yang Liu, Yutao Rao, Gakhyun Kim, Mingbo Zhou, Donghai Yu, Ling Xu, Bangshao Yin, Shubin Liu, Takayuki Tanaka, Naoki Aratani, Atsuhiro Osuka, Qingyun Liu, Dongho Kim, Jianxin Song

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18 Citations (Scopus)


All-aza smaragdyrin, a historic but elusive pentapyrrolic macrocycle, was successfully synthesized and characterized for the first time. [22]Smaragdyrin BF 2 -complex 3 was smoothly synthesized by 2-fold S N Ar reaction of 1,9-dibromo-5-mesityldipyrrin with 5,10-dimesityltripyrrane. Treatment of 3 with methanesulfonic acid gave [20]smaragdyrin 5 as a stable antiaromatic compound. Reduction of 5 with NaBH 4 under inert conditions gave [22]smaragdyrin 6 as an aromatic congener, which was easily oxidized back to 5 in the air. Complex 3 was interconvertible with its 20?-congener 4 via oxidation with MnO 2 and reduction with NaBH 4 . Treatment of 3 or 4 with CuCl 2 in the presence of NaOAc gave hetero bimetal complex 8.

Original languageEnglish
Pages (from-to)16553-16559
Number of pages7
JournalJournal of the American Chemical Society
Issue number48
Publication statusPublished - 2018 Dec 5

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Xie, D., Liu, Y., Rao, Y., Kim, G., Zhou, M., Yu, D., Xu, L., Yin, B., Liu, S., Tanaka, T., Aratani, N., Osuka, A., Liu, Q., Kim, D., & Song, J. (2018). Meso-Triaryl-Substituted Smaragdyrins: Facile Aromaticity Switching. Journal of the American Chemical Society, 140(48), 16553-16559.