PEGylated perylene bisimides: Chromonic building blocks for the aqueous synthesis of nanostructured silica materials

Perylene dyes have applications in many fields. Herewith, we report on the synthesis and properties of a series of PEGylated perylene bisimides with varying PEG chain lengths. Such molecules are formed by a hydrophobic perylene core functionalized at the imide positions with hydrophilic non-ionic fu...

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Detalles Bibliográficos
Autores: Pérez-Calm, Adrià, Esquena, Jordi, Salonen, Laura M., Rodríguez-Abreu, Carlos
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/222578
Acceso en línea:http://hdl.handle.net/10261/222578
Access Level:acceso abierto
Palabra clave:Perylene bisimide
Self-assembly
Chromonic liquid crystal
Descripción
Sumario:Perylene dyes have applications in many fields. Herewith, we report on the synthesis and properties of a series of PEGylated perylene bisimides with varying PEG chain lengths. Such molecules are formed by a hydrophobic perylene core functionalized at the imide positions with hydrophilic non-ionic functional groups, which impart solubility and capacity to self-assemble in water. The diluted solutions of the synthesized molecules show interesting optical and fluorescent properties that depend on solvent and concentration; they also show surface activity and a lower critical solution temperature. Moreover, at high concentrations, the molecules produce lyotropic chromonic liquid crystals with nematic and hexagonal structures, formed by aligned molecular stacks. Such mesostructures were successfully exploited for the preparation of hybrid silica materials with ordered perylene nanostripes that generate aligned nanopores (of ca. 1.4 nm) upon calcination. It was found that the distance between perylene nanostripes and hence the pore wall thickness can be finely tuned by changing the length of the PEG chain.