ArticleOrganic chemistry frontiers : an international journal of organic chemistry2021
Functional group introduction and aromatic unit variation in a set of π-conjugated macrocycles: revealing the central role of local and global aromaticity.
Article in Organic chemistry frontiers : an international journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
12 citing papers in PubMed.
- Computational investigation of antioxidant activities and mechanisms of catechol analogues through a DFT study.Journal of computer-aided molecular design · 2026Article
- The (Anti)aromatic Properties of Cyclo[n]Carbons: Myth or Reality?Journal of computational chemistry · 2025Article
- A fully conjugated meso-boron-substituted porphyrinoid combining Lewis acidity with redox-switchable aromaticity.Nature communications · 2025Article
- Concealed antiaromaticity.Open research Europe · 2025Article
- Research advances in nanomaterials with aromatic functional groups for the treatment of inflammatory bowel disease.Frontiers in bioengineering and biotechnology · 2025Review
- Reducing undesired solubility of squarephaneic tetraimide for use as an organic battery electrode material.Faraday discussions · 2024Article
- Crystallographic evidence for global aromaticity in the di-anion and tetra-anion of a cyclophane hydrocarbon.Chemical science · 2023Article
- Functionalisation of conjugated macrocycles with type I and II concealed antiaromaticityMolecular systems design & engineering · 2023Article
- Alternating behavior in furan-acetylene macrocycles reveals the size-dependency of Hückel's rule in neutral molecules.Communications chemistry · 2023Article
- Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials.Angewandte Chemie (International ed. in English) · 2022Article
- Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- [2.2.2.2]Paracyclophanetetraenes (PCTs): cyclic structural analogues of poly(Open research Europe · 2021Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
π-Conjugated macrocycles are molecules with unique properties that are increasingly exploited for applications and the question of whether they can sustain global aromatic or antiaromatic ring currents is particularly intriguing. However, there are only a small number of experimental studies that investigate how the properties of π-conjugated macrocycles evolve with systematic structural changes. Here, we present such a systematic experimental study of a set of [2.2.2.2]cyclophanetetraenes, all with formally Hückel antiaromatic ground states, and combine it with an in-depth computational analysis. The study reveals the central role of local and global aromaticity for rationalizing the observed optoelectronic properties, ranging from extremely large Stokes shifts of up to 1.6 eV to reversible fourfold reduction, a highly useful feature for charge storage/accumulation applications. A recently developed method for the visualization of chemical shielding tensors (VIST) is applied to provide unique insight into local and global ring currents occurring in different planes along the macrocycle. Conformational changes as a result of the structural variations can further explain some of the observations. The study contributes to the development of structure-property relationships and molecular design guidelines and will help to understand, rationalize, and predict the properties of other π-conjugated macrocycles. It will also assist in the design of macrocycle-based supramolecular elements with defined properties.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.