Self-assembled bright luminescent hierarchical materials from a tripodal benzoate antenna and heptadentate Eu(III) and Tb(III) cyclen complexes

doi:10.1007/s11705-018-1762-3

Front. Chem. Sci. Eng.

2019, Vol. 13

Issue (1) : 171-184 https://doi.org/10.1007/s11705-018-1762-3

RESEARCH ARTICLE

Self-assembled bright luminescent hierarchical materials from a tripodal benzoate antenna and heptadentate Eu(III) and Tb(III) cyclen complexes

Aramballi J. Savyasachi¹, David F. Caffrey¹, Kevin Byrne², Gerard Tobin², Bruno D'Agostino¹, Wolfgang Schmitt², Thorfinnur Gunnlaugsson¹(

)

¹. School of Chemistry and Trinity Biomedical Sciences Institute (TBSI), University of Dublin, Trinity College Dublin, Dublin 2, Ireland
². School of Chemistry and Centre for Research on Adaptive Nanostructures and Nanodevices (CRANN), University of Dublin, Trinity College Dublin, Dublin 2, Ireland

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Abstract

The europium heptadentate coordinatively unsaturated (Eu(III)) and the terbium (Tb(III)) 1,4,7,10-tetraazacyclododecane (cyclen) complexes 1 and 2 were used in conjunction with ligand 3 (1,3,5-benzene-trisethynylbenzoate) to form the supramolecular self-assembly structures 4 and 5; this being investigated in both the solid and the solution state. The resulting self-assemblies gave rise to metal centered emission (both in the solid and solution) upon excitation of 3, confirming its role as a sensitizing antenna. Drop-cased examples of ligand 3, and the solid forms of 4 and 5, formed from both organic and mixture of organic-aqueous solutions, were analyzed using Scanning Electron Microscopy, which showed significant changes in morphology; the ligand giving rise to one dimensional structures, while both 4 and 5 formed amorphous materials that were highly dense solid networks containing nanoporous features. The surface area (216 and 119 m²·g⁻¹ for 4 and 5 respectively) and the ability of these porous materials to capture and store gases such as N₂ investigated at 77 K. The self-assembly formation was also investigated in diluted solution by monitoring the various photophysical properties of 3–5. This demonstrated that the most stable structures were that consisting of a single antennae 3 and three complexes of 1 or 2 (e.g., 4 and 5) in solution. By monitoring the excited state lifetimes of the Eu(III) and Tb(III) ions in H₂O and D₂O respectively, we showed that their hydration states (the q-value) changed from ~2 to 0, upon formation of the assemblies, indicating that the three benzoates of 3 coordinated directly to the each of the three lanthanide centers. Finally we demonstrate that this hierarchically porous materials can be used for the sensing of organic solvents as the emission is highly depended on the solvent environment; the lanthanide emission being quenched in the presence of acetonitrile and THF, but greatly enhanced in the presence of methanol.

Keywords self-assembly supramolecular chemistry lanthanides Eu(III) and Tb(III) complexes luminescence metallostars

Corresponding Author(s): Thorfinnur Gunnlaugsson

Just Accepted Date: 10 July 2018 Online First Date: 12 December 2018 Issue Date: 25 February 2019

Cite this article:

Aramballi J. Savyasachi,David F. Caffrey,Kevin Byrne, et al. Self-assembled bright luminescent hierarchical materials from a tripodal benzoate antenna and heptadentate Eu(III) and Tb(III) cyclen complexes[J]. Front. Chem. Sci. Eng., 2019, 13(1): 171-184.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-018-1762-3
https://academic.hep.com.cn/fcse/EN/Y2019/V13/I1/171

Fig.1 The structures of the 1,3,5-benzene-trisethynylbenzoate 3, and the cationic cyclen lanthanide complexes 1 and 2. The displacement of the two metal bound water molecules of 1 and 2 by the antenna 3, results in the formation of the ternary complexes, 4 and 5. These are luminescent, giving rise to lanthanide centered emission upon excitation of the antenna which results in energy transfer to the lanthanide excited state

Fig.2 (a) Diagram of the self-assembly ternary complex formation between 1 or 2 and 3 resulting in the formation of 4 and 5; (b) the characteristic red and green luminescence seen to the naked eye upon exposing the white powder obtained of 4 and 5 to UV-light at 354 nm; (c) the characteristic Eu(III) and Tb(III) lanthanide centered emission, showing the line-line emission bands at long wavelengths, upon excitation of 4 and 5, and the corresponding excitation spectra demonstrating that the excitation at the central tripodal antenna sensitizes the Eu(III) and the Tb(III) excited states

Fig.3 The SEM images obtained from samples of 0.5% wt·v⁻¹ solutions of 3 in THF (left) and 1:1 THF-H₂O (right) drop-casted onto silica wafers, scale bar 2 μm

Fig.4 SEM images of the dropcasted solutions of 4 in (a–c) THF, CH₃CN and MeOH and (d–f) the corresponding aqueous mixtures (1:1, v·v⁻¹) THF-H₂O, CH₃CN-H₂O and MeOH-H₂O, respectively

Fig.5 SEM images of the dropcasted solutions of 5 in (a–c) THF, CH₃CN and MeOH and (d–f) the corresponding aqueous mixtures (1:1, v·v⁻¹) THF-H₂O, CH₃CN-H₂O and MeOH-H₂O, respectively

Fig.6 SEM images taken at higher magnifications of the dropcasted solutions of (a–c) 4 and (d–f) 5 in aqueous mixtures (1:1, v·v⁻¹) THF-H₂O, CH₃CN-H₂O and MeOH-H₂O, respectively

Fig.7 N₂ adsorption-desorption isotherm of (a) 4 and (b) 5 measured at 77 K. Inset: corresponding pore size distribution curve

Fig.8 Solid state emission spectrum of (a) 4 and (b) 5 recorded in dry state (black) and presence of THF (red), CH₃CN (blue) and MeOH (pink)

Tab.1 Summarized t values for solid state Eu(III) and Tb(III) emission from 4 and 5 in dry state and in presence of organic solvents

Fig.9 (a) Changes in the absorption spectra of 3 (2.5 × 10⁻⁶ mol·L⁻¹) upon titrating with Eu(III) complex 1 (0.00 → 6.00 eq.) in 0.1 mol·L⁻¹ Tris aqueous buffer (pH 7.4) at 298 K (Insert: Binding isotherms for the changes observed at 296 nm and 314 nm, respectively); (b) the evolution of the (phosphorescence) delayed Eu(III) emission of 4 with l_exc = 296 nm demonstrating the formation of 4 in situ (Inset: Binding isotherms for the changes observed at 593 nm, 616 nm, and 700 nm); (c) the speciation-distribution diagram obtained from the fitting of the change in the absorption spectra (seen in Fig. 9(a)) using the nonlinear regression analysis program SPECFIT, demonstrating the stepwise formation of the 1:3 stoichiometry of 4 from 1 and 3

Tab.2 Summary of t_H2O and t_D2O values of Eu(III) and the q values of the species during the titrations between 3 and 1 in H2O and D2O

Fig.10 (a) Changes in the absorption spectra of 3 (2.5 × 10⁻⁶ mol·L⁻¹) upon titrating with Eu(III) complex 2 (0.00 → 6.00 eq.) in 0.1 mol·L⁻¹ Tris aqueous buffer (pH 7.4) at 298 K (Insert: Binding isotherms for the changes observed at 296 nm and 314 nm, respectively); (b) the evolution of the (phosphorescence) delayed Tb(III) emission of 5 with l_exc = 296 nm demonstrating the formation of 4 in situ (Inset: Binding isotherms for the changes observed at 490, 545, and 586 nm); (c) the speciation-distribution diagram obtained from the fitting of the change in the absorption spectra (seen in Fig. 9(a)) using the nonlinear regression analysis program SPECFIT, demonstrating the stepwise formation of the 1:3 stoichiometry of 5 from 2 and 3

Tab.3 Summary of t_H2O and t_D2O values of Tb(III) and q values of the species during the titrations between 3 and 2 in H₂O and D₂O

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