Synthesis and characterization of two fluorescent isophthalate rosamines: From solution to immobilization in solid substrates. (October 2018)

• Record Type: Journal Article
• Authors: Queirós, Carla; Leite, Andreia; Cunha-Silva, Luís; de Castro, Baltazar; Rangel, Maria; Sousaraei, Ahmad; Cabanillas-Gonzalez, Juan; Gámez, Francisco; Jamardo, Estefanía; Vargas, Alejandro P.; Moscoso, Francisco G.; Lopes-Costa, Tânia; Pedrosa, José M.; Silva, Ana M.G.
• Is Part Of: Dyes and pigments. Volume 157(2018)
• Page Start: 405
• Page End: 414
• Publication Date: 2018-10
• Subjects: Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2018.05.005
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: The design of fluorescent molecules with structural features for efficient immobilization in polymeric supports or binding matrixes is an active research topic, which aims to create materials with optical and mechanical properties suitable for sensing applications. Herein, we describe the synthesis and characterization of two new fluorescent ligands prepared by a combination of a rosamine platform and an isophthalate receptor using amine and amide linkages. In order to evaluate their potential application as fluorescence sensors, the photophysical properties of the ligands were accessed by UV-Vis and photoluminescence measurements in solution and after immobilization (infiltrated in TiO2 thin films). Furthermore, molecular and electronic structures of both ligands were rationalized by DFT and TD-DFT calculations. Interesting features were found for the ligand containing an amide bond, which has shown to be less prone to aggregation and has higher emission capacity, being a promising candidate in fluorescence sensor devices. Graphical abstract: Highlights: Two new fluorescent ligands were prepared by a combination of a rosamine platform with an isophthalate receptor using amine and amide linkages. Photophysical properties (UV-Vis and photoluminescence) were measured. Molecular and electronic structure calculations were performed using Density Functional Theory in gas phase and Time-Dependent Density Functional Theory in DMSO. TiO2 thin films infiltrated with the resulting ligands were prepared and their absorption and emission properties were studied. The ligand containing an amide bond showed to be less prone to aggregation and possessed higher emission capacity, being a promising candidate in fluorescence sensor devices.