RT info:eu-repo/semantics/article
T1 Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines
A1 Monteiro-Silva, Filipe
A1 Queirós, Carla
A1 Leite, Andreia
A1 Rodríguez Rodríguez, Mª Teresa
A1 Rojo Cámara, Mª Josefa
A1 Torroba Pérez, Tomás
A1 Martins, Rui C.
A1 Silva, Ana M. G.
A1 Rangel, Maria
K1 Microwave-assisted synthesis
K1 Catecholated rosamines
K1 9-aminopyronins
K1 Photophysical properties
K1 Biogenic amines detection
K1 Química orgánica
K1 Chemistry, Organic
AB 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.
PB MDPI
SN 1420-3049
YR 2021
FD 2021-08
LK http://hdl.handle.net/10259/6138
UL http://hdl.handle.net/10259/6138
LA eng
NO Financial support from PT national funds (FCT/MCTES, Fundação para a Ciência e a Tecnologia and Ministério da Ciência, Tecnologia e Ensino Superior) through the project PTDC/QUI-QOR/29426/2017. The research team would like to thank the projects UIDB/50006/2020, PTDC/QUI-QIN/28142/2017 and Grant BU263P18 (from the Junta de Castilla y León, Consejería de Educación y Cultura y Fondo Social Europeo). F. M. -S. gratefully acknowledges FCT (Portugal’s Foundation for Science and Technology) within grant DFA/BD/9136/2020. A.M.G.S. and A.L. thank FCT for the program DL 57/2016 – Norma transitória.
DS Repositorio Institucional de la Universidad de Burgos
RD 21-nov-2024