ArticleBeilstein journal of organic chemistry2016
Synthesis and properties of fluorescent 4'-azulenyl-functionalized 2,2':6',2″-terpyridines.
Article in Beilstein journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed.
- Synthesis of azulene fluorophores reveals structure-property relationships.Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Synthesis, Physicochemical Properties, and Ion Recognition Ability of Azulene-Based Bis-(Thio)Semicarbazone.Molecules (Basel, Switzerland) · 2024Article
- Solvent Effect on the Photophysical Properties of Terpyridine Incorporating Pyrene Moiety: Estimation of Dipole Moments by Solvatochromic Shift Methods.Journal of fluorescence · 2023Article
- Second order nonlinear optical properties of poled films containing azobenzenes tailored with azulen-1-yl-pyridine.Heliyon · 2023Article
- Design, Synthesis, and Biological Evaluation of New Azulene-Containing Chalcones.Materials (Basel, Switzerland) · 2022Article
- Terpyridine-metal complexes: effects of different substituents on their physico-chemical properties and density functional theory studies.Royal Society open science · 2020Article
- Development of Heterocycle-Substituted and Fused Azulenes in the Last Decade (2010-2020).International journal of molecular sciences · 2020Review
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8 authors.
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Abstract
4'-Azulenyl-substituted terpyridines were efficiently synthesized following the Kröhnke methodology via azulenylchalcone intermediates. These azulenyl-containing terpyridines showed fluorescent emission with a fluorescence quantum yield varying from 0.14, in the case of parent terpyridine, to 0.64 when methyl groups are grafted on the azulenyl seven-membered ring. According to the crystal structures and TDDFT calculations, different twisting of the aromatic constituents is responsible for the observed fluorescent behavior. The electrochemical profile contains one-electron oxidation/reduction steps, which can only be explained on the basis of the redox behavior of the azulene unit. The ability of the 4'-azulenyl 2,2':6',2″-terpyridine to bind poisoning metal cations was studied by UV-vis titrations using aqueous solutions of Hg(II) and Cd(II) chlorides as illustrative examples.
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