Concepedia

Metalation of Expanded Porphyrins: A Chemical Trigger Used To Produce Molecular Twisting and Möbius Aromaticity

Yasuo Tanaka, Shohei Saito, Shigeki Mori, Naoki Aratani, Hiroshi Shinokubo, Naoki Shibata, Yoshiki Higuchi, Zin Seok Yoon, Kil Suk Kim, Su Bum Noh,

Angewandte Chemie International Edition · 2007 · 325 citations · 18 references

DOIFull text

Open access

Concepts

Abstract

Round the twist: Metalation of [36]octaphyrin 1 provided the Möbius aromatic Pd2 complex 3 as well as the Hückel antiaromatic Pd2 complex 2. This method can be applied to other expanded porphyrins and Group 10 metal ions. The aromatic/antiaromatic character was supported by NMR spectrscopy, NICS calculation, and two-photon absorption measurements.

References

18

Sensitive measurement of optical nonlinearities using a single beam

Mansoor Sheik‐Bahae, A. A. Said, Tai‐Huei Wei et al. · IEEE Journal of Quantum Electronics · 1990 · 9K citations · Full text

, , +16

Synthetic Expanded Porphyrin Chemistry

Jonathan L. Sessler, Daniel Seidel · Angewandte Chemie International Edition · 2003 · 915 citations · Full text

, , +15

Hűckel molecular orbitals of Mőbius-type conformations of annulenes

E. Heilbronner · Tetrahedron Letters · 1964 · 525 citations

, , +12

Expanded Porphyrin with a Split Personality: A Hückel–Möbius Aromaticity Switch

Marcin Stępień, Lechosław Latos‐Grażyński, Natasza Sprutta et al. · Angewandte Chemie International Edition · 2007 · 344 citations

, , +7

On Molecular Orbital Correlation Diagrams, the Occurrence of Möbius Systems in Cyclization Reactions, and Factors Controlling Ground- and Excited-State Reactions. I

Howard E. Zimmerman · Journal of the American Chemical Society · 1966 · 296 citations

, , +8