Novel Luminescent Ionic Adducts Based on Pyrene-1-sulfonate

Abstract

The potential of pyrene-1-sulfonate to act as an emitting anion for the development of ionic liquids is explored here. Amphiphilic trimethylpropylammonium hepta(isooctyl)octasilsesquioxane and conventional imidazolium, namely, 1-vinyl-3-hexyl-, 1-vinyl-3-decyl-, and 1-methyl-3-decyl-imidazolium, featuring moderate alkyl chain length substituents, have been chosen as countercations. The new species have been synthesized via simple metathesis reactions involving pyrene-1-sulfonate sodium salt and the appropriate halide cation precursors. Their thermal behavior has been investigated by thermogravimetric and differential scanning calorimetry at different scanning rates. According to this latter technique, only the trimethylpropylammonium hepta(isooctyl)octasilsesquioxane pyrenesulfonate adduct, displaying a reversible glass transition at −4.2 °C, may be classified as an ionic liquid. All pyrene-1-sulfonate imidazolium-based ion pairs are crystalline solids with the melting point just above 100 °C that produce very complex, nonreversible, and scanning rate-dependent thermograms, very likely arising from polymorphism phenomena. Such a behavior may be attributed to the pyrene-1-sulfonate polycyclic system, which in solution, as confirmed through spectroscopic characterization, displays a general attitude in promoting supramolecular structures via cation interactions. Emission lifetime measurements on the emitting fluorophore reveal that there are at least two different active species, whereas light scattering measurements show the presence of aggregates with hydrodynamic radii depending on the medium and adduct concentration. Tests aimed at investigating the potential of these novel pyrene-1-sulfonate salts in functionalization/exfoliation of graphite flakes are also reported here.

Pyrenesulfonic Acid Sodium Salt for Effective Bottom‐Surface Passivation to Attain High Performance of Perovskite Solar Cells

“…Figure 1c shows the device external quantum efficiency (EQE) and integrated J sc , device with PyNa þ achieved high EQE, especially in the low wavelength region because of the enhanced absorption properties by fluorescence property of PyNa þ . [44] The integrated J sc of devices for control, bottom, surface and double are 23.94, 24.02, 24.55, and 24.82 mA cm À2 , which match well with the J sc from the J-V cures. Steady-state output at the maximum power point (MPP) voltage is also an important property for devices, Figure S1, Supporting Information, shows the stabilized PCEs of devices.…”

“…Figure 4b shows the light absorption spectral features, the absorption shows almost the same spectrum in long wavelength region and greatly enhanced intensity in 400-600 nm wavelength region, which consists with the absorption results. As reported, [44] the materials of PyNa þ process the property of photoluminescence (PL), the PL spectrum is shown in Figure S4, Supporting Information. Therefore, www.advancedsciencenews.com www.solar-rrl.com absorption of perovskite film with PyNa þ can be greatly enhanced.…”

Noncovalent Functionalization of 2D Black Phosphorus with Fluorescent Boronic Derivatives of Pyrene for Probing and Modulating the Interaction with Molecular Oxygen

“…Considering these evidences, the bi- or triexponential decay fitting curves are clearly indicative of the presence in solution of two or three different species that we can justify by only speculating on the monomeric, dimeric, or oligomeric nature of the fluorophore, as previously reported for pyrene sulphonate derivatives. 58…”

“…Considering these evidences, the bi-or triexponential decay fitting curves are clearly indicative of the presence in solution of two or three different species that we can justify by only speculating on the monomeric, dimeric, or oligomeric nature of the fluorophore, as previously reported for pyrene sulphonate derivatives. 58 The fluorescence decays of the three adducts were fitted with biexponential decay for Py and triexponential decays for PBA and PBE, respectively. In all three cases, the presence of 2D BP leads to an increase in the fluorescence lifetime values.…”