Development of Efficient One-Pot Methods for the Synthesis of Luminescent Dyes and Sol-Gel Hybrid Materials

• Published in: Materials Vol. 15; no. 1; p. 203
• Main Authors: Zdończyk, Maria, Potaniec, Bartłomiej, Skoreński, Marcin, Cybińska, Joanna
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 28.12.2021; MDPI
• Subjects: Acids; Alkylation; Aqueous solutions; Ball milling; Chromatography; Dyes; Equilibrium; Fluorescein; fluorescein derivative; Fluorescence; luminescence; Nitrogen; NMR; Nuclear magnetic resonance; organic dyes; Reaction time; Silicon dioxide; Sol-gel processes; sol–gel; United States > US; Germany; organic dyes; fluorescein derivative; luminescence; sol–gel
• ISSN: 1996-1944; 1996-1944
• DOI: 10.3390/ma15010203

This paper presents a comparison of the simultaneous preparation of di- -alkylated and ether-ester derivatives of fluorescein using different methods (conventional or microwave heating). Shortening of the reaction time and increased efficiency were observed when using a microwave reactor. Moreover, described here for the first time is the application of a fast, simple, and eco-friendly ball-assisted method to exclusively obtain ether-ester derivatives. We also demonstrate that fluorescein can be effectively functionalized by -alkylation carried out under microwave or ball-milling conditions, saving time and energy and affording the desired products with good yields and minimal byproduct formation. All the synthesized products as well as pH-dependent (prototropic) forms trapped in the SiO matrix were examined using UV-Vis and fluorescence spectroscopy.