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

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

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
Volume140
Issue number48
DOIs
Publication statusPublished - 2018 Dec 5

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Bimetals
Oxidation
Acids
Air
22pi smaragdyrin
methanesulfonic acid

All Science Journal Classification (ASJC) codes

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

Cite this

Xie, D., Liu, Y., Rao, Y., Kim, G., Zhou, M., Yu, D., ... Song, J. (2018). Meso-Triaryl-Substituted Smaragdyrins: Facile Aromaticity Switching. Journal of the American Chemical Society, 140(48), 16553-16559. https://doi.org/10.1021/jacs.8b07973
Xie, Daguan ; Liu, Yang ; Rao, Yutao ; Kim, Gakhyun ; Zhou, Mingbo ; Yu, Donghai ; Xu, Ling ; Yin, Bangshao ; Liu, Shubin ; Tanaka, Takayuki ; Aratani, Naoki ; Osuka, Atsuhiro ; Liu, Qingyun ; Kim, Dongho ; Song, Jianxin. / Meso-Triaryl-Substituted Smaragdyrins : Facile Aromaticity Switching. In: Journal of the American Chemical Society. 2018 ; Vol. 140, No. 48. pp. 16553-16559.
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abstract = "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.",
author = "Daguan Xie and Yang Liu and Yutao Rao and Gakhyun Kim and Mingbo Zhou and Donghai Yu and Ling Xu and Bangshao Yin and Shubin Liu and Takayuki Tanaka and Naoki Aratani and Atsuhiro Osuka and Qingyun Liu and Dongho Kim and Jianxin Song",
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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, vol. 140, no. 48, pp. 16553-16559. https://doi.org/10.1021/jacs.8b07973

Meso-Triaryl-Substituted Smaragdyrins : Facile Aromaticity Switching. / Xie, Daguan; Liu, Yang; Rao, Yutao; Kim, Gakhyun; Zhou, Mingbo; Yu, Donghai; Xu, Ling; Yin, Bangshao; Liu, Shubin; Tanaka, Takayuki; Aratani, Naoki; Osuka, Atsuhiro; Liu, Qingyun; Kim, Dongho; Song, Jianxin.

In: Journal of the American Chemical Society, Vol. 140, No. 48, 05.12.2018, p. 16553-16559.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Meso-Triaryl-Substituted Smaragdyrins

T2 - Facile Aromaticity Switching

AU - Xie, Daguan

AU - Liu, Yang

AU - Rao, Yutao

AU - Kim, Gakhyun

AU - Zhou, Mingbo

AU - Yu, Donghai

AU - Xu, Ling

AU - Yin, Bangshao

AU - Liu, Shubin

AU - Tanaka, Takayuki

AU - Aratani, Naoki

AU - Osuka, Atsuhiro

AU - Liu, Qingyun

AU - Kim, Dongho

AU - Song, Jianxin

PY - 2018/12/5

Y1 - 2018/12/5

N2 - 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.

AB - 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.

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