doi: 10.1039/c6cc02051h.
Epub 2016 Apr 12.
Multifaceted [36]octaphyrin(1.1.1.1.1.1.1.1): deprotonation-induced switching among nonaromatic, Möbius aromatic, and Hückel antiaromatic species
Affiliations
- PMID: 27067645
- DOI: 10.1039/c6cc02051h
Item in Clipboard
Multifaceted [36]octaphyrin(1.1.1.1.1.1.1.1): deprotonation-induced switching among nonaromatic, Möbius aromatic, and Hückel antiaromatic species
Chem Commun (Camb).
.
Abstract
Deprotonation of nonaromatic octakis-(pentafluorophenyl)-substituted [36]octaphyrin(1.1.1.1.1.1.1.1) with tetrabutylammonium fluoride (TBAF) afforded monoanionic twisted Möbius aromatic species and dianinonic square Hückel antiaromatic species, depending upon the amount of TBAF.
Similar articles
-
5,20-Di(pyridin-2-yl)-[28]hexaphyrin(1.1.1.1.1.1): A Stable Hückel Antiaromatic Hexaphyrin Stabilized by Intramolecular Hydrogen Bonding and Protonation-Induced Conformational Twist To Gain Möbius Aromaticity.J Org Chem. 2015 Dec 4;80(23):11726-33. doi: 10.1021/acs.joc.5b01348. Epub 2015 Aug 4. J Org Chem. 2015. PMID: 26218902
-
Protonated [4n]pi and [4n+2]pi octaphyrins choose their Möbius/Hückel aromatic topology.J Am Chem Soc. 2010 Mar 10;132(9):3105-14. doi: 10.1021/ja909744z. J Am Chem Soc. 2010. PMID: 20148589
-
A Doubly Zwitterionic Antiaromatic [28]Hexaphyrin Formed upon Deprotonation of 5,20-Di(N-methyl-4-pyridinium)-Substituted [28]Hexaphyrin.Chem Asian J. 2016 Oct 20;11(20):2849-2853. doi: 10.1002/asia.201601071. Epub 2016 Sep 14. Chem Asian J. 2016. PMID: 27529538
-
The Extension of Baird's Rule to Twisted Heteroannulenes: Aromaticity Reversal of Singly and Doubly Twisted Molecular Systems in the Lowest Triplet State.Angew Chem Int Ed Engl. 2017 Mar 6;56(11):2932-2936. doi: 10.1002/anie.201611431. Epub 2017 Feb 6. Angew Chem Int Ed Engl. 2017. PMID: 28165184
-
Pd(II) complexes of [44]- and [46]decaphyrins: the largest Hückel aromatic and antiaromatic, and Möbius aromatic macrocycles.Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13169-73. doi: 10.1002/anie.201408506. Epub 2014 Sep 24. Angew Chem Int Ed Engl. 2014. PMID: 25258332
Cited by
-
Open shell (4n + 2)π and closed shell 4nπ planar core-modified decaphyrins.Chem Sci. 2024 Mar 11;15(16):6022-6027. doi: 10.1039/d3sc05251f. eCollection 2024 Apr 24. Chem Sci. 2024. PMID: 38665541 Free PMC article.
-
Tetratellura[36]octaphyrin(1.1.1.1.1.1.1.1) Metalation: From Dynamic Behavior to Rigid Chiral Figure-of-Eight Molecule; Activation of the C-Te Bond by Ruthenium.Inorg Chem. 2024 Nov 18;63(46):21788-21800. doi: 10.1021/acs.inorgchem.4c03506. Epub 2024 Nov 6. Inorg Chem. 2024. PMID: 39503349 Free PMC article.
-
Mechanochemically Triggered Topology Changes in Expanded Porphyrins.Chemistry. 2021 Feb 15;27(10):3397-3406. doi: 10.1002/chem.202003869. Epub 2021 Jan 18. Chemistry. 2021. PMID: 33170967 Free PMC article.
-
Quest for the Most Aromatic Pathway in Charged Expanded Porphyrins.Chemistry. 2023 Jan 27;29(6):e202202264. doi: 10.1002/chem.202202264. Epub 2022 Nov 28. Chemistry. 2023. PMID: 36194440 Free PMC article.
-
Stereochemical plasticity modulates cooperative binding in a CoII12L6 cuboctahedron.Nat Chem. 2017 Sep;9(9):903-908. doi: 10.1038/nchem.2758. Epub 2017 Apr 10. Nat Chem. 2017. PMID: 28837174
Publication types
LinkOut - more resources
Full Text Sources
Other Literature Sources
