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 0.64 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.
"C. D. Nenitzescu" Institute of Organic Chemistry of the Romanian Academy, 202 B Splaiul Independentei, 060023, Bucharest, Romania; Inorganic Chemistry Laboratory, Faculty of Chemistry, University of Bucharest, Str. Dumbrava Rosie, 020464, Bucharest, Romania.
Adrian E
AE
Ion
"C. D. Nenitzescu" Institute of Organic Chemistry of the Romanian Academy, 202 B Splaiul Independentei, 060023, Bucharest, Romania; Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, Bd. Regina Elisabeta 4-12, Bucharest 030016, Romania.
Liliana
L
Cristian
"Ilie Murgulescu" Institute of Physical Chemistry of the Romanian Academy, Splaiul Independentei 202, 060021, Bucharest, Romania.
Mariana
M
Voicescu
Department of Chemistry, Hazara University, Mansehra 21120, Pakistan.
Masroor
M
Bangesh
Inorganic Chemistry Laboratory, Faculty of Chemistry, University of Bucharest, Str. Dumbrava Rosie, 020464, Bucharest, Romania.
Augustin M
AM
Madalan
Physical Chemistry Department, Faculty of Chemistry, University of Bucharest, Regina Elisabeta, no. 4-12, 030018, Bucharest, Romania.
Daniela
D
Bala
Physical Chemistry Department, Faculty of Chemistry, University of Bucharest, Regina Elisabeta, no. 4-12, 030018, Bucharest, Romania.
Constantin
C
Mihailciuc
"C. D. Nenitzescu" Institute of Organic Chemistry of the Romanian Academy, 202 B Splaiul Independentei, 060023, Bucharest, Romania.
Simona
S
Nica
azulene; fluorescence; metal binding; synthesis; terpyridine