Synthesis and properties of fluorescent 4'-azulenyl-functionalized 2,2':6',2″-terpyridines

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...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2016-08, Vol.12 (1), p.1812-1825
Main Authors: Ion, Adrian E, Cristian, Liliana, Voicescu, Mariana, Bangesh, Masroor, Madalan, Augustin M, Bala, Daniela, Mihailciuc, Constantin, Nica, Simona
Format: Article
Language:English
Subjects:
azulene
Chemistry
fluorescence
Full Research Paper
metal binding
synthesis
terpyridine
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Summary: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.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.12.171