Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties

A series of pyrimidine derivatives bearing one, two or three triphenylamine/9-ethylcarbazole substituents has been synthesized by Suzuki cross-coupling reaction. All compounds showed absorption bands in the UV region and the emission of violet-blue light upon irradiation. Protonation led to quenchin...

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Main Authors: Sylvain Achelle, Julián Rodríguez-López, Massinissa Larbani, Rodrigo Plaza-Pedroche, Françoise Robin-le Guen
Format: Article
Language:English
Published: MDPI AG 2019-05-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/24/9/1742
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author Sylvain Achelle
Julián Rodríguez-López
Massinissa Larbani
Rodrigo Plaza-Pedroche
Françoise Robin-le Guen
author_facet Sylvain Achelle
Julián Rodríguez-López
Massinissa Larbani
Rodrigo Plaza-Pedroche
Françoise Robin-le Guen
author_sort Sylvain Achelle
collection DOAJ
description A series of pyrimidine derivatives bearing one, two or three triphenylamine/9-ethylcarbazole substituents has been synthesized by Suzuki cross-coupling reaction. All compounds showed absorption bands in the UV region and the emission of violet-blue light upon irradiation. Protonation led to quenching of the fluorescence, although some derivatives remained luminescent with the appearance of a new red-shifted band in the spectra. Accurate control of the amount of acid enabled white photoluminescence to be obtained both in solution and in solid state.
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spelling doaj.art-1eb1cc2f173146e693bad26e9f5d094e2022-12-22T02:36:38ZengMDPI AGMolecules1420-30492019-05-01249174210.3390/molecules24091742molecules24091742Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical PropertiesSylvain Achelle0Julián Rodríguez-López1Massinissa Larbani2Rodrigo Plaza-Pedroche3Françoise Robin-le Guen4Université de Rennes, CNRS, Institut des Sciences Chimiques de Rennes-UMR 6226, F 35000 Rennes, FranceÁrea de Química Orgánica, Facultad de Ciencias y Tecnologías Químicas, Universidad de Castilla-La-Mancha, Avda. Camillo José Cela 10, 13071 Ciudad Real, SpainUniversité de Rennes, CNRS, Institut des Sciences Chimiques de Rennes-UMR 6226, F 35000 Rennes, FranceÁrea de Química Orgánica, Facultad de Ciencias y Tecnologías Químicas, Universidad de Castilla-La-Mancha, Avda. Camillo José Cela 10, 13071 Ciudad Real, SpainUniversité de Rennes, CNRS, Institut des Sciences Chimiques de Rennes-UMR 6226, F 35000 Rennes, FranceA series of pyrimidine derivatives bearing one, two or three triphenylamine/9-ethylcarbazole substituents has been synthesized by Suzuki cross-coupling reaction. All compounds showed absorption bands in the UV region and the emission of violet-blue light upon irradiation. Protonation led to quenching of the fluorescence, although some derivatives remained luminescent with the appearance of a new red-shifted band in the spectra. Accurate control of the amount of acid enabled white photoluminescence to be obtained both in solution and in solid state.https://www.mdpi.com/1420-3049/24/9/1742pyrimidinesfluorescencewhite-light emissionintramolecular charge transfer
spellingShingle Sylvain Achelle
Julián Rodríguez-López
Massinissa Larbani
Rodrigo Plaza-Pedroche
Françoise Robin-le Guen
Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties
Molecules
pyrimidines
fluorescence
white-light emission
intramolecular charge transfer
title Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties
title_full Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties
title_fullStr Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties
title_full_unstemmed Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties
title_short Carbazole- and Triphenylamine-Substituted Pyrimidines: Synthesis and Photophysical Properties
title_sort carbazole and triphenylamine substituted pyrimidines synthesis and photophysical properties
topic pyrimidines
fluorescence
white-light emission
intramolecular charge transfer
url https://www.mdpi.com/1420-3049/24/9/1742
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AT julianrodriguezlopez carbazoleandtriphenylaminesubstitutedpyrimidinessynthesisandphotophysicalproperties
AT massinissalarbani carbazoleandtriphenylaminesubstitutedpyrimidinessynthesisandphotophysicalproperties
AT rodrigoplazapedroche carbazoleandtriphenylaminesubstitutedpyrimidinessynthesisandphotophysicalproperties
AT francoiserobinleguen carbazoleandtriphenylaminesubstitutedpyrimidinessynthesisandphotophysicalproperties