Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage

Eight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluorescent dyes have been investigated. Furtherm...

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Main Authors: Henning Weiss, Jeannine Reichel, Helmar Görls, Kilian Rolf Anton Schneider, Mathias Micheel, Michael Pröhl, Michael Gottschaldt, Benjamin Dietzek, Wolfgang Weigand
Format: Article
Language:English
Published: Beilstein-Institut 2017-10-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.13.223
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author Henning Weiss
Jeannine Reichel
Helmar Görls
Kilian Rolf Anton Schneider
Mathias Micheel
Michael Pröhl
Michael Gottschaldt
Benjamin Dietzek
Wolfgang Weigand
author_facet Henning Weiss
Jeannine Reichel
Helmar Görls
Kilian Rolf Anton Schneider
Mathias Micheel
Michael Pröhl
Michael Gottschaldt
Benjamin Dietzek
Wolfgang Weigand
author_sort Henning Weiss
collection DOAJ
description Eight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluorescent dyes have been investigated. Furthermore, a strategy for the hydrolysis of the BF2 group has been established using aqueous methanol and sodium hydroxide or triethylamine.
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spelling doaj.art-dc0afb8faf074402b1efa894939ddadb2022-12-21T20:01:43ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-10-011312264227210.3762/bjoc.13.2231860-5397-13-223Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavageHenning Weiss0Jeannine Reichel1Helmar Görls2Kilian Rolf Anton Schneider3Mathias Micheel4Michael Pröhl5Michael Gottschaldt6Benjamin Dietzek7Wolfgang Weigand8Institute for Inorganic and Analytical Chemistry, Friedrich-Schiller-Universität Jena, Humboldtstrasse 8, 07743 Jena, GermanyInstitute for Inorganic and Analytical Chemistry, Friedrich-Schiller-Universität Jena, Humboldtstrasse 8, 07743 Jena, GermanyInstitute for Inorganic and Analytical Chemistry, Friedrich-Schiller-Universität Jena, Humboldtstrasse 8, 07743 Jena, GermanyInstitute for Physical Chemistry, Friedrich-Schiller-Universität Jena, Helmholtzweg 4, 07743 Jena, GermanyLeibniz Institute of Photonic Technology (IPHT), Albert-Einstein-Straße 9, 07745 Jena, GermanyJena Center of Soft Matter, Friedrich-Schiller-Universität Jena, Philosophenweg 7, 07743 Jena, GermanyJena Center of Soft Matter, Friedrich-Schiller-Universität Jena, Philosophenweg 7, 07743 Jena, GermanyInstitute for Physical Chemistry, Friedrich-Schiller-Universität Jena, Helmholtzweg 4, 07743 Jena, GermanyInstitute for Inorganic and Analytical Chemistry, Friedrich-Schiller-Universität Jena, Humboldtstrasse 8, 07743 Jena, GermanyEight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluorescent dyes have been investigated. Furthermore, a strategy for the hydrolysis of the BF2 group has been established using aqueous methanol and sodium hydroxide or triethylamine.https://doi.org/10.3762/bjoc.13.223BF2 complexcurcumindyesfluorescencehydrolysisspectroscopy
spellingShingle Henning Weiss
Jeannine Reichel
Helmar Görls
Kilian Rolf Anton Schneider
Mathias Micheel
Michael Pröhl
Michael Gottschaldt
Benjamin Dietzek
Wolfgang Weigand
Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage
Beilstein Journal of Organic Chemistry
BF2 complex
curcumin
dyes
fluorescence
hydrolysis
spectroscopy
title Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage
title_full Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage
title_fullStr Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage
title_full_unstemmed Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage
title_short Curcuminoid–BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage
title_sort curcuminoid bf2 complexes synthesis fluorescence and optimization of bf2 group cleavage
topic BF2 complex
curcumin
dyes
fluorescence
hydrolysis
spectroscopy
url https://doi.org/10.3762/bjoc.13.223
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