Möbius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation

Kang Park Jong; Seok Yoon Zin; Min Chul Yoon; Suk Kim Kil; Shigeki Mori; Ji Young Shin; Atsuhiro Osuka; Dongho Kim

doi:10.1021/ja7100483

Möbius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation

Kang Park Jong, Seok Yoon Zin, Min Chul Yoon, Suk Kim Kil, Shigeki Mori, Ji Young Shin, Atsuhiro Osuka, Dongho Kim

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

N-fused pentaphyrins (NFP₅), stable forms of meso-aryl pentaphyrins, are interesting platforms to realize Hückel aromaticity, nonaromaticity, and Möbius aromaticity depending upon the number of π-electrons, meso-substituent, and metalation. Remarkably, Rh(I) complex of pentakis(pentafluorophenyl) substituted [24]NFP₅ has been characterized as a Möbius aromatic macrocycle by the crystal structure, 1H NMR spectrum, NICS calculation, and two-photon absorption (TPA) cross section. This system is, to the best of our knowledge, the smallest Möbius aromatic molecule with a distinct diatropic ring current characterized so far. This work demonstrates the great potential of our synthetic strategy toward Möbius aromatic molecules as well as the possible use of TPA value as a quantitative measure of aromaticity.

Original language	English
Pages (from-to)	1824-1825
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	6
DOIs	https://doi.org/10.1021/ja7100483
Publication status	Published - 2008 Feb 13

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja7100483

Cite this

@article{0a33124578544c149a61df526fcd7424,

title = "M{\"o}bius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation",

abstract = "N-fused pentaphyrins (NFP5), stable forms of meso-aryl pentaphyrins, are interesting platforms to realize H{\"u}ckel aromaticity, nonaromaticity, and M{\"o}bius aromaticity depending upon the number of π-electrons, meso-substituent, and metalation. Remarkably, Rh(I) complex of pentakis(pentafluorophenyl) substituted [24]NFP5 has been characterized as a M{\"o}bius aromatic macrocycle by the crystal structure, 1H NMR spectrum, NICS calculation, and two-photon absorption (TPA) cross section. This system is, to the best of our knowledge, the smallest M{\"o}bius aromatic molecule with a distinct diatropic ring current characterized so far. This work demonstrates the great potential of our synthetic strategy toward M{\"o}bius aromatic molecules as well as the possible use of TPA value as a quantitative measure of aromaticity.",

author = "Jong, {Kang Park} and Zin, {Seok Yoon} and Yoon, {Min Chul} and Kil, {Suk Kim} and Shigeki Mori and Shin, {Ji Young} and Atsuhiro Osuka and Dongho Kim",

year = "2008",

month = feb,

day = "13",

doi = "10.1021/ja7100483",

language = "English",

volume = "130",

pages = "1824--1825",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Möbius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation

AU - Jong, Kang Park

AU - Zin, Seok Yoon

AU - Yoon, Min Chul

AU - Kil, Suk Kim

AU - Mori, Shigeki

AU - Shin, Ji Young

AU - Osuka, Atsuhiro

AU - Kim, Dongho

PY - 2008/2/13

Y1 - 2008/2/13

N2 - N-fused pentaphyrins (NFP5), stable forms of meso-aryl pentaphyrins, are interesting platforms to realize Hückel aromaticity, nonaromaticity, and Möbius aromaticity depending upon the number of π-electrons, meso-substituent, and metalation. Remarkably, Rh(I) complex of pentakis(pentafluorophenyl) substituted [24]NFP5 has been characterized as a Möbius aromatic macrocycle by the crystal structure, 1H NMR spectrum, NICS calculation, and two-photon absorption (TPA) cross section. This system is, to the best of our knowledge, the smallest Möbius aromatic molecule with a distinct diatropic ring current characterized so far. This work demonstrates the great potential of our synthetic strategy toward Möbius aromatic molecules as well as the possible use of TPA value as a quantitative measure of aromaticity.

AB - N-fused pentaphyrins (NFP5), stable forms of meso-aryl pentaphyrins, are interesting platforms to realize Hückel aromaticity, nonaromaticity, and Möbius aromaticity depending upon the number of π-electrons, meso-substituent, and metalation. Remarkably, Rh(I) complex of pentakis(pentafluorophenyl) substituted [24]NFP5 has been characterized as a Möbius aromatic macrocycle by the crystal structure, 1H NMR spectrum, NICS calculation, and two-photon absorption (TPA) cross section. This system is, to the best of our knowledge, the smallest Möbius aromatic molecule with a distinct diatropic ring current characterized so far. This work demonstrates the great potential of our synthetic strategy toward Möbius aromatic molecules as well as the possible use of TPA value as a quantitative measure of aromaticity.

UR - http://www.scopus.com/inward/record.url?scp=39049146261&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=39049146261&partnerID=8YFLogxK

U2 - 10.1021/ja7100483

DO - 10.1021/ja7100483

M3 - Article

C2 - 18198878

AN - SCOPUS:39049146261

SN - 0002-7863

VL - 130

SP - 1824

EP - 1825

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 6

ER -

Möbius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this