ArticleJournal of the American Chemical Society2023
Excited-State (Anti)Aromaticity Explains Why Azulene Disobeys Kasha's Rule.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed.
- Synthesis of azulene fluorophores reveals structure-property relationships.Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Synthesis and Characterization of Zinc Complexes with Diethyl 2‑Hydroxyazulene-1,3-dicarboxylate as a Ligand.ACS omega · 2026Article
- Linearly Expanded Azulenes in theJournal of computational chemistry · 2026Article
- Azulene as an anomaly in triplet-state engineeringChemical science · 2026Article
- Cycloazulenylene.Angewandte Chemie (International ed. in English) · 2026Article
- Molecular orbital node engineering in pyrene: linking chemical reactivity with room-temperature phosphorescence.National science review · 2026Article
- Azulene-Fused Polycyclic Aromatic Hydrocarbons: Synthesis, Structural, Optical, and Electrochemical Properties of Azuleno[1,2,3-cd]Benzo[mn]Pyrene-8,14-diones and Cyclohepta[1,2]Indeno[6,5,4-de]Anthracen-9-ones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Deactivating Emission in Azulene via Solvent-Induced (Anti)Aromaticity.Journal of the American Chemical Society · 2026Article
- Decarbonylation Enables Chemodivergent Access to Guaiazulene-3-Oxalic and -Carboxylic Acid Derivatives.The Journal of organic chemistry · 2026Article
- Benzo[cd]azulenyl: A Structural Isomer of Phenalenyl-Synthesis and Properties of Its Tri-tert-butyl-substituted Derivative and Formation of a Thermal- and Photoresponsive σ-Dimer.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- A CJournal of the American Chemical Society · 2026Article
- Mechanistic Design in Photocatalysis.Accounts of chemical research · 2026Article
- Craig Excited-State Aromaticity in Metallabenzenes: How, When, and Why?Journal of the American Chemical Society · 2026Article
- Homomolecular Photon Upconversion in a Perylene-Decorated Iron(III) Complex.Journal of the American Chemical Society · 2025Article
- Structural Elucidation and Antiviral Activity Evaluation of Novelly Synthesized Guaiazulene Derivatives.Marine drugs · 2025Article
- Reaction of Diethyl 2‑Hydroxyazulene-1,3-dicarboxylate with Metal Acetates and Alkoxides: Metal Complex Formation and Transesterification.ACS omega · 2025Article
- Lewis Acid-Catalyzed Alkylation of Azulene Derivatives with Epoxides and Oxetanes: A Regioselective Approach to Functionalized Azulene Alcohols.Organic letters · 2025Article
- Breaking Kasha's Rule to Enable Higher Reactivity in Photoredox Catalysis.Journal of the American Chemical Society · 2025Article
- Synthesis of l-β-(6-azulenyl)alanine and the fluorescent actin disruptor (6-azuleno)chalasin H.RSC advances · 2025Article
- Rhodium-Catalyzed Intermolecular Arylative [2 + 2 + 1] Annulation-Oxidation to Produce Electron-Deficient Azulene-Embedded Polycyclic Aromatic Hydrocarbons.Angewandte Chemie (International ed. in English) · 2025Article
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Fluorescence exclusively occurs from the lowest excited state of a given multiplicity according to Kasha's rule. However, this rule is not obeyed by a handful of anti-Kasha fluorophores whose underlying mechanism is still understood merely on a phenomenological basis. This lack of understanding prevents the rational design and property-tuning of anti-Kasha fluorophores. Here, we propose a model explaining the photophysical properties of an archetypal anti-Kasha fluorophore, azulene, based on its ground- and excited-state (anti)aromaticity. We derived our model from a detailed analysis of the electronic structure of the ground singlet, first excited triplet, and quintet states and of the first and second excited singlet states using the perturbational molecular orbital theory and quantum-chemical aromaticity indices. Our model reveals that the anti-Kasha properties of azulene and its derivatives result from (i) the contrasting (anti)aromaticity of its first and second singlet excited states (S
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