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- Title
Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines.
- Authors
Monteiro-Silva, Filipe; Queirós, Carla; Leite, Andreia; Rodríguez, María T.; Rojo, María J.; Torroba, Tomás; Martins, Rui C.; Silva, Ana M. G.; Rangel, Maria
- Abstract
Functional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine 4, which also showed the most interesting photophysical properties, specially toward biogenic amines (BAs). Several amines including n- and t-butylamine, cadaverine, and putrescine cause spectral changes of 4, in UV–Vis and fluorescence spectra, which are indicative of their potential application as an effective tool to detect amines in acetonitrile solutions. In the gas phase, the probe response is more expressive for spermine and putrescine. Additionally, we found that methanolic solutions of rosamine 4 and n-butylamine undergo a pink to yellow color change over time, which has been attributed to the formation of a new compound. The latter was isolated and identified as 5 (9−aminopyronin), whose solutions exhibit a remarkable increase in fluorescence intensity together with a shift toward more energetic wavelengths. Other 9-aminopyronins 6a, 6b, 7a, and 7b were obtained from methanolic solutions of 4 with putrescine and cadaverine, demonstrating the potential of this new xanthene entity to react with primary amines.
- Subjects
BIOGENIC amines; PINK; CATECHOL; FLUORESCENCE spectroscopy; CHEMICAL yield; ORGANIC dyes; PUTRESCINE
- Publication
Molecules, 2021, Vol 26, Issue 16, p5082
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules26165082