Diarylethene-Based Ionic Liquids: Synthesis and Photo-Driven Solution Properties
| Autor: | Carlos Alberto Mateus Afonso, Mário Soromenho, José Esperança |
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| Přispěvatelé: | LAQV@REQUIMTE, DQ - Departamento de Química |
| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | International Journal of Molecular Sciences Volume 24 Issue 4 Pages: 3533 |
| Popis: | Funding text The authors acknowledge Fundação para a Ciência e Tecnologia through the PhD grant SFRH/BD/81693/2011 (M. R. C. Soromenho). This work was supported by the Associate Laboratory for Green Chemistry-LAQV (Portugal) (UIDB/50006/2020, UIDP/50006/2020, and LA/P/0008/2020) and by the Instituto de Investigação do Medicamento (iMed.ULisboa) (UIDB/04138/2020, and UIDP/04138/2020) which are financed by national funds from FCT/MCTES. The NMR spectrometers are part of the National NMR Network (PTNMR) are partially supported by Infrastructure Project Nº 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC). In this work, the design and synthesis of a series of photochromic gemini diarylethene-based ionic liquids (GDILs) with different cationic motifs is reported. Several synthetic pathways were optimized for the formation of cationic GDILs with chloride as the counterion. The different cationic motifs were achieved through the N-alkylation of the photochromic organic core unit with different tertiary amines, including different aromatic amines such as imidazole derivatives and pyridinium, and other non-aromatic amines. These novel salts present surprising water solubility with unexplored photochromic features that broaden their known applications. The covalent attachment of the different side groups dictates their water solubility and differences upon photocyclization. The physicochemical properties of GDILs in aqueous and in imidazolium-based ionic liquid (IL) solutions were investigated. Upon irradiation with ultraviolet (UV) light, we have observed changes in the physico-chemical properties of distinct solutions containing these GDILs, at very low concentrations. More specifically, in aqueous solution, the overall conductivity increased with the time of UV photoirradiation. In contrast, in IL solution, these photoinducible changes are dependent on the type of ionic liquid used. These compounds can improve non-ionic and ionic liquids’ solutions since we can change their properties, such as conductivity, viscosity or ionicity, only by UV photoirradiation. The electronic and conformational changes associated with these innovative stimuli GDILs may open new opportunities for their use as photoswitchable materials. publishersversion published |
| Databáze: | OpenAIRE |
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