Efficient Sensitization of Lanthanide Luminescence by Tetrazole-Based Polydentate Ligands

Giraud, Marion; Andreiadis, Eugen S.; Fisyuk, A. S.; Demadrille, Renaud; Pécaut, Jacques; Imbert, Daniel; Mazzanti, Marinella

doi:10.1021/ic8005663

Cited by 92 publications

(50 citation statements)

References 25 publications

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“…It should also be noted that some of the aromatic rings in the ligands are slightly bowed, a feature that is often found in complexes with high coordination numbers even in phenanthroline 40 rings. 32 A bowed arrangement of 5 is also observed in the crystal structure of Y (5) 33 In this crystallographic 50 structure, the metal ion occupies the center of an irregular bicapped trigonal prismatic assembly of nitrogen atoms that is close to a square antiprismatic arrangement. The induced paramagnetic shifts δ i were computed from the spectra of Yb (5) as a reference.…”

Section: Nuclear Magnetic Resonance and Theoretical Studiesmentioning

confidence: 79%

Interaction of 6,6′′-bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-1,2,4-benzotriazin-3-yl)-2,2′:6′,2′′-terpyridine (CyMe4-BTTP) with some trivalent ions such as lanthanide(iii) ions and americium(iii)

et al. 2010

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Section: Nuclear Magnetic Resonance and Theoretical Studiesmentioning

confidence: 79%

Interaction of 6,6′′-bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-1,2,4-benzotriazin-3-yl)-2,2′:6′,2′′-terpyridine (CyMe4-BTTP) with some trivalent ions such as lanthanide(iii) ions and americium(iii)

et al. 2010

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“…Conversely, a preliminary study from our group indicated that tetrazolates can act as efficient sensitizers of lanthanide luminescence. [16] Moreover, tetrazolates have attracted considerable interest in coordination chemistry due to their [17] p-acceptor properties and to their ability to form metal complexes and coordination polymers with high thermal stability and display interesting luminescence, nonlinear optical, electrochemical, and H 2 storage properties.…”

Section: Introductionmentioning

confidence: 99%

“…To prevent water binding we decided to include tetrazolate groups in higher denticity ligands. [16] Bipyridine and terpyridine were chosen as suitable building blocks because their chemistry is well known and the coordination properties of bipyridine-carboxylate and terpyridine-carboxylate ligands and the luminescent properties of their lanthanide complexes have been extensively investigated. [10,[23][24][25] This should allow for a facile comparison of the effect of tetrazolate substitution with respect to carboxylate on the excitation wavelength and luminescence quantum yields of isostructural lanthanide complexes.…”

Section: Introductionmentioning

confidence: 99%

Remarkable Tuning of the Coordination and Photophysical Properties of Lanthanide Ions in a Series of Tetrazole‐Based Complexes

Andreiadis

Demadrille

Imbert

et al. 2009

Chemistry A European J

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111

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A series of seven new tetrazole-based ligands (L1, L3-L8) containing terpyridine or bipyridine chromophores suited to the formation of luminescent complexes of lanthanides have been synthesized. All ligands were prepared from the respective carbonitriles by thermal cycloaddition of sodium azide. The crystal structures of the homoleptic terpyridine-tetrazolate complexes [Ln(Li)(2)]NHEt(3) (Ln = Nd, Eu, Tb for i = 1, 2; Ln = Eu for i = 3, 4) and of the monoaquo bypyridine-tetrazolate complex [Eu(H(2)O)(L7)(2)]NHEt(3) were determined. The tetradentate bipyridine-tetrazolate ligand forms nonhelical complexes that can contain a water molecule coordinated to the metal. Conversely, the pentadentate terpyridine-tetrazolate ligands wrap around the metal, thereby preventing solvent coordination and forming chiral double-helical complexes similarly to the analogue terpyridine-carboxylate. Proton NMR spectroscopy studies show that the solid-state structures of these complexes are retained in solution and indicate the kinetic stability of the hydrophobic complexes of terpyridine-tetrazolates. UV spectroscopy results suggest that terpyridine-tetrazolate complexes have a similar stability to their carboxylate analogues, which is sufficient for their isolation in aerobic conditions. The replacement of the carboxylate group with tetrazolate extends the absorption window of the corresponding terpyridine- (approximately 20 nm) and bipyridine-based (25 nm) complexes towards the visible region (up to 440 nm). Moreover, the substitution of the terpyridine-tetrazolate system with different groups in the ligand series L3-L6 has a very important effect on both absorption spectra and luminescence efficiency of their lanthanide complexes. The tetrazole-based ligands L1 and L3-L8 sensitize efficiently the luminescent emission of lanthanide ions in the visible and near-IR regions with quantum yields ranging from 5 to 53% for Eu(III) complexes, 6 to 35% for Tb(III) complexes, and 0.1 to 0.3% for Nd(III) complexes, which is among the highest reported for a neodymium complex. The luminescence efficiency could be related to the energy of the ligand triplet states, which are strongly correlated to the ligand structures.

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“…It is noteworthy that the most used methods toward the synthesis of the 1,5-DS-1H-T are both click [3 + 2] dipolar cycloadditions of organic azides with cyanides [4][5][6][7] and the Ugi-azide reaction between amines, aldehydes, isocyanides and hydrazoic acid [8]. , allowing the synthesis of various potent luminescent materials [9]. The bis-sulfide-tetrazoles 4, which were biologically tested by Waisser and co-workers, showed a strong antiulcer, as well as antimycobacterial activity [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel bis-1,5-Disubstituted-1H-Tetrazoles by an Efficient Catalyst-Free Ugi-Azide Repetitive Process

et al. 2015

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A series of five novel bis-1,5-disubstituted-1H-tetrazoles (bis-1,5-DS-1H-T) were quickly prepared by a catalyst-free Ugi-azide repetitive process from easily accessible starting materials in excellent yields, either at room temperature (88%-95%) or using mild MW-heating conditions (80%-91%). These molecules may have a wide range of applications, such as chelating agents, organocatalysts and luminescent materials, and mainly as bioactive compounds.

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Efficient Sensitization of Lanthanide Luminescence by Tetrazole-Based Polydentate Ligands

Cited by 92 publications

References 25 publications

Interaction of 6,6′′-bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-1,2,4-benzotriazin-3-yl)-2,2′:6′,2′′-terpyridine (CyMe4-BTTP) with some trivalent ions such as lanthanide(iii) ions and americium(iii)

Interaction of 6,6′′-bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-1,2,4-benzotriazin-3-yl)-2,2′:6′,2′′-terpyridine (CyMe4-BTTP) with some trivalent ions such as lanthanide(iii) ions and americium(iii)

Remarkable Tuning of the Coordination and Photophysical Properties of Lanthanide Ions in a Series of Tetrazole‐Based Complexes

Synthesis of Novel bis-1,5-Disubstituted-1H-Tetrazoles by an Efficient Catalyst-Free Ugi-Azide Repetitive Process

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