ArticleCommunications chemistry2023
Alternating behavior in furan-acetylene macrocycles reveals the size-dependency of Hückel's rule in neutral molecules.
Article in Communications chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 10 citations in OpenAlex.
- Conjugated Macrocycles for Host-Guest Recognition and Optoelectronic Applications.Advanced materials (Deerfield Beach, Fla.) · 2026Review
- Enlarged-TriQuinoline (Enl-TQ): Disparity in Chemical Behaviors by Geometric Scaling of the Trimeric Quinoline Ring System.Chemistry, an Asian journal · 2025Article
- Precise Synthesis of Ester-Functionalized Cyclo[6]- and Cyclo[7]furans.The Journal of organic chemistry · 2025Article
- Odd-Even Effects Leading to Alternating Polymerization and Macrocyclization in Nitroaldol Reaction Systems.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Concealed antiaromaticity.Open research Europe · 2025Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Aromaticity can be assigned by Hückel's rule, which predicts that planar rings with delocalized (4n + 2) π-electrons are aromatic, whereas those with 4n π-electrons are antiaromatic. However, for neutral rings, the maximal value of "n" to which Hückel's rule applies remains unknown. Large macrocycles exhibiting global ring current can serve as models for addressing this question, but the global ring current are often overshadowed in these molecules by the local ring current of the constituent units. Here, we present a series of furan-acetylene macrocycles, ranging from the pentamer to octamer, whose neutral states display alternating contributions from global aromatic and antiaromatic ring currents. We find that the odd-membered macrocycles display global aromatic characteristics, whereas the even-membered macrocycles display contributions from globally antiaromatic ring current. These factors are expressed electronically (oxidation potentials), optically (emission spectra), and magnetically (chemical shifts), and DFT calculations predict global ring current alternations up to 54 π-electrons.
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Registered trials
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