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Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions
Quantum-chemical calculations on the spectral properties of some aryl substituted 3-phosphonocoumarins were performed, and the effect of the substituents in the aryl moiety was evaluated. The structures possessing promising fluorescent properties were successfully synthesized via Suzuki and Sonogash...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9654183/ https://www.ncbi.nlm.nih.gov/pubmed/36364471 http://dx.doi.org/10.3390/molecules27217649 |
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author | Lyapchev, Rumen Koleva, Ana I. Koleva, Iskra Z. Subev, Kristian Madzharova, Ivelina Simeonova, Kristina B. Petkova-Yankova, Nevena Morgenstern, Bernd Lozanova, Vesela Petrov, Petar Y. Nikolova, Rositca D. |
author_facet | Lyapchev, Rumen Koleva, Ana I. Koleva, Iskra Z. Subev, Kristian Madzharova, Ivelina Simeonova, Kristina B. Petkova-Yankova, Nevena Morgenstern, Bernd Lozanova, Vesela Petrov, Petar Y. Nikolova, Rositca D. |
author_sort | Lyapchev, Rumen |
collection | PubMed |
description | Quantum-chemical calculations on the spectral properties of some aryl substituted 3-phosphonocoumarins were performed, and the effect of the substituents in the aryl moiety was evaluated. The structures possessing promising fluorescent properties were successfully synthesized via Suzuki and Sonogashira cross-coupling. The synthetic protocol was also applied for the phosphorous chemoisomer of 3-phosphonocoumarin, 1,2-benzoxaphosphorin, and their carboxylate analogues. The optical properties of the arylated and alkynylated products were experimentally determined. The obtained quantum-chemical and experimental results give the possibility for a fine tuning of the optical properties of phosphorous-containing coumarin systems by altering the substituent at its C-6 position. |
format | Online Article Text |
id | pubmed-9654183 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-96541832022-11-15 Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions Lyapchev, Rumen Koleva, Ana I. Koleva, Iskra Z. Subev, Kristian Madzharova, Ivelina Simeonova, Kristina B. Petkova-Yankova, Nevena Morgenstern, Bernd Lozanova, Vesela Petrov, Petar Y. Nikolova, Rositca D. Molecules Article Quantum-chemical calculations on the spectral properties of some aryl substituted 3-phosphonocoumarins were performed, and the effect of the substituents in the aryl moiety was evaluated. The structures possessing promising fluorescent properties were successfully synthesized via Suzuki and Sonogashira cross-coupling. The synthetic protocol was also applied for the phosphorous chemoisomer of 3-phosphonocoumarin, 1,2-benzoxaphosphorin, and their carboxylate analogues. The optical properties of the arylated and alkynylated products were experimentally determined. The obtained quantum-chemical and experimental results give the possibility for a fine tuning of the optical properties of phosphorous-containing coumarin systems by altering the substituent at its C-6 position. MDPI 2022-11-07 /pmc/articles/PMC9654183/ /pubmed/36364471 http://dx.doi.org/10.3390/molecules27217649 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Lyapchev, Rumen Koleva, Ana I. Koleva, Iskra Z. Subev, Kristian Madzharova, Ivelina Simeonova, Kristina B. Petkova-Yankova, Nevena Morgenstern, Bernd Lozanova, Vesela Petrov, Petar Y. Nikolova, Rositca D. Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions |
title | Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions |
title_full | Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions |
title_fullStr | Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions |
title_full_unstemmed | Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions |
title_short | Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions |
title_sort | efficient synthesis of fluorescent coumarins and phosphorous-containing coumarin-type heterocycles via palladium catalyzed cross-coupling reactions |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9654183/ https://www.ncbi.nlm.nih.gov/pubmed/36364471 http://dx.doi.org/10.3390/molecules27217649 |
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