Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives

Lade...
Vorschaubild
Dateien
Amaya-Garcia_2-1c12xxq2a173g0.pdf
Amaya-Garcia_2-1c12xxq2a173g0.pdfGröße: 1.52 MBDownloads: 194
Datum
2021
Autor:innen
Amaya-García, Fabián
Caldera, Michael
Koren, Anna
Kubicek, Stefan
Menche, Jörg
Herausgeber:innen
Kontakt
ISSN der Zeitschrift
Electronic ISSN
ISBN
Bibliografische Daten
Verlag
Schriftenreihe
Auflagebezeichnung
ArXiv-ID
Internationale Patentnummer
Link zur Lizenz
Angaben zur Forschungsförderung
Projekt
Open Access-Veröffentlichung
Open Access Hybrid
Sammlungen
Core Facility der Universität Konstanz
Gesperrt bis
Titel in einer weiteren Sprache
Forschungsvorhaben
Organisationseinheiten
Zeitschriftenheft
Publikationstyp
Zeitschriftenartikel
Publikationsstatus
Published
Erschienen in
ChemSusChem. Wiley. 2021, 14(8), pp. 1853-1863. ISSN 1864-5631. eISSN 1864-564X. Available under: doi: 10.1002/cssc.202100433
Zusammenfassung

Here, the hydrothermal synthesis (HTS) of 2,3-diarylquinoxalines from 1,2-diketones and o-phenylendiamines (o-PDAs) was achieved. The synthesis is simple, fast, and generates high yields, without requiring any organic solvents, strong acids or toxic catalysts. Reaction times down to <10 min without decrease in yield could be achieved through adding acetic acid as promoter, even for highly apolar biquinoxalines (yield >90 % in all cases). Moreover, it was shown that HTS has high compatibility: (i) hydrochlorides, a standard commercial form of amines, could be used directly as combined amine source and acidic catalyst, and (ii) Boc-diprotected o-PDA could be directly employed as substrate that underwent HT deprotection. A systematic large-scale computational comparison of all reported syntheses of the presented quinoxalines from the same starting compounds showed that this method is more environmentally friendly and less toxic than all existing methods and revealed generic synthetic routes for improving reaction yields. Finally, the application of the synthesized compounds as fluorescent dyes for cell staining was explored.

Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
540 Chemie
Schlagwörter
Konferenz
Rezension
undefined / . - undefined, undefined
Zitieren
ISO 690AMAYA-GARCÍA, Fabián, Michael CALDERA, Anna KOREN, Stefan KUBICEK, Jörg MENCHE, Miriam M. UNTERLASS, 2021. Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives. In: ChemSusChem. Wiley. 2021, 14(8), pp. 1853-1863. ISSN 1864-5631. eISSN 1864-564X. Available under: doi: 10.1002/cssc.202100433
BibTex
@article{AmayaGarcia2021-04-22Green-54802,
  year={2021},
  doi={10.1002/cssc.202100433},
  title={Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives},
  number={8},
  volume={14},
  issn={1864-5631},
  journal={ChemSusChem},
  pages={1853--1863},
  author={Amaya-García, Fabián and Caldera, Michael and Koren, Anna and Kubicek, Stefan and Menche, Jörg and Unterlass, Miriam M.}
}
RDF
<rdf:RDF
    xmlns:dcterms="http://purl.org/dc/terms/"
    xmlns:dc="http://purl.org/dc/elements/1.1/"
    xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#"
    xmlns:bibo="http://purl.org/ontology/bibo/"
    xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#"
    xmlns:foaf="http://xmlns.com/foaf/0.1/"
    xmlns:void="http://rdfs.org/ns/void#"
    xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > 
  <rdf:Description rdf:about="https://kops.uni-konstanz.de/server/rdf/resource/123456789/54802">
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2021-09-03T08:38:42Z</dc:date>
    <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by/4.0/"/>
    <dc:creator>Unterlass, Miriam M.</dc:creator>
    <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/54802"/>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2021-09-03T08:38:42Z</dcterms:available>
    <dc:rights>Attribution 4.0 International</dc:rights>
    <dc:contributor>Caldera, Michael</dc:contributor>
    <dc:creator>Kubicek, Stefan</dc:creator>
    <dc:creator>Amaya-García, Fabián</dc:creator>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/54802/1/Amaya-Garcia_2-1c12xxq2a173g0.pdf"/>
    <dc:contributor>Unterlass, Miriam M.</dc:contributor>
    <dc:creator>Menche, Jörg</dc:creator>
    <dc:contributor>Kubicek, Stefan</dc:contributor>
    <dc:contributor>Amaya-García, Fabián</dc:contributor>
    <dc:contributor>Menche, Jörg</dc:contributor>
    <dc:language>eng</dc:language>
    <dcterms:title>Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives</dcterms:title>
    <dc:creator>Caldera, Michael</dc:creator>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/54802/1/Amaya-Garcia_2-1c12xxq2a173g0.pdf"/>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dc:contributor>Koren, Anna</dc:contributor>
    <dc:creator>Koren, Anna</dc:creator>
    <dcterms:issued>2021-04-22</dcterms:issued>
    <dcterms:abstract xml:lang="eng">Here, the hydrothermal synthesis (HTS) of 2,3-diarylquinoxalines from 1,2-diketones and o-phenylendiamines (o-PDAs) was achieved. The synthesis is simple, fast, and generates high yields, without requiring any organic solvents, strong acids or toxic catalysts. Reaction times down to &lt;10 min without decrease in yield could be achieved through adding acetic acid as promoter, even for highly apolar biquinoxalines (yield &gt;90 % in all cases). Moreover, it was shown that HTS has high compatibility: (i) hydrochlorides, a standard commercial form of amines, could be used directly as combined amine source and acidic catalyst, and (ii) Boc-diprotected o-PDA could be directly employed as substrate that underwent HT deprotection. A systematic large-scale computational comparison of all reported syntheses of the presented quinoxalines from the same starting compounds showed that this method is more environmentally friendly and less toxic than all existing methods and revealed generic synthetic routes for improving reaction yields. Finally, the application of the synthesized compounds as fluorescent dyes for cell staining was explored.</dcterms:abstract>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
  </rdf:Description>
</rdf:RDF>
Interner Vermerk
xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter
Kontakt
URL der Originalveröffentl.
Prüfdatum der URL
Prüfungsdatum der Dissertation
Finanzierungsart
Kommentar zur Publikation
Allianzlizenz
Corresponding Authors der Uni Konstanz vorhanden
Internationale Co-Autor:innen
Universitätsbibliographie
Ja
Begutachtet
Ja
Diese Publikation teilen