title: Sustainable design for environment-friendly mono and dicationic cholinium-based ionic liquids.
abstract: Cholinium-based ionic liquids are receiving crescent interest in diverse areas of application given their biological compatibility and potential for industrial application. In this work, mono and dicationic cholinium ionic liquids as well as cholinium derivatives were synthesized and their toxicity assessed using the luminescent bacteria Vibrio fischeri. A range of cholinium derivatives was synthesized, using different amines and the correspondent brominated derivatives, through the alkylation of the amine with the halide in MeCN. The results indicate that their toxicity is highly dependent on the structural modifications of the cholinium cation, mainly related to the alkyl side or linkage chain length, number of hydroxyethyl groups and insertion of carbon-carbon multiple bonds. The data indicated that it is possible to perform environmentally advantageous structural alterations, namely the addition of double bonds, which would not negatively affect V. fischeri. Moreover, the dicationic compounds revealed a significantly lower toxicity than the monocationic counterparts. The picture emerging from the results supports the idea that cholinium derivatives are promising ionic liquids with a low environmental impact, emphasizing the importance of a careful and directed design of ionic liquid structures.
authors.affiliation: CICECO, Departamento de Química, Universidade de Aveiro, 3810-193 Aveiro, Portugal.
authors.forename: Francisca A
authors.initials: FA
authors.lastname: E Silva
authors.affiliation: Instituto de Investigação do Medicamento (iMed.ULisboa), Faculdade de Farmácia da Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
authors.forename: Filipa
authors.initials: F
authors.lastname: Siopa
authors.affiliation: CICECO, Departamento de Química, Universidade de Aveiro, 3810-193 Aveiro, Portugal.
authors.forename: Bruna F H T
authors.initials: BF
authors.lastname: Figueiredo
authors.affiliation: Departamento de Biologia, CESAM (Centro de Estudos do Ambiente e do Mar), Universidade de Aveiro, 3810-193 Aveiro, Portugal; IMAR-Centro do Mar e Ambiente (IMAR CMA), Departamento das Ciências da Vida, Universidade de Coimbra, 3004-517 Coimbra, Portugal.
authors.forename: Ana M M
authors.initials: AM
authors.lastname: Gonçalves
authors.affiliation: Departamento de Biologia, CESAM (Centro de Estudos do Ambiente e do Mar), Universidade de Aveiro, 3810-193 Aveiro, Portugal.
authors.forename: Joana L
authors.initials: JL
authors.lastname: Pereira
authors.affiliation: Departamento de Biologia, CESAM (Centro de Estudos do Ambiente e do Mar), Universidade de Aveiro, 3810-193 Aveiro, Portugal.
authors.forename: Fernando
authors.initials: F
authors.lastname: Gonçalves
authors.affiliation: CICECO, Departamento de Química, Universidade de Aveiro, 3810-193 Aveiro, Portugal.
authors.forename: João A P
authors.initials: JA
authors.lastname: Coutinho
authors.affiliation: Instituto de Investigação do Medicamento (iMed.ULisboa), Faculdade de Farmácia da Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal.
authors.forename: Carlos A M
authors.initials: CA
authors.lastname: Afonso
authors.affiliation: CICECO, Departamento de Química, Universidade de Aveiro, 3810-193 Aveiro, Portugal. Electronic address: spventura@ua.pt.
authors.forename: Sónia P M
authors.initials: SP
authors.lastname: Ventura
mesh_terms: D048908:Aliivibrio fischeri; D002412:Cations; D055772:Green Chemistry Technology; D052578:Ionic Liquids / Q000737:chemistry / Q000633:toxicity*; D018675:Toxicity Tests
chemical_list: D002412:Cations; D052578:Ionic Liquids
keywords: Cholinium; Dicationic; Ionic liquids; Median effect concentration (EC(50)); Microtox(®) test; Monocationic