Flavin-Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface-Supported Films.
flavins
helicenes
lipidic cubic phases
redox behavior
thin layers
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
11 May 2021
11 May 2021
Historique:
revised:
20
04
2021
received:
25
02
2021
pubmed:
13
5
2021
medline:
13
5
2021
entrez:
12
5
2021
Statut:
aheadofprint
Résumé
This work reports on the preparation and structural characterization of flavo[7]helicene 1 (flavin-[7]helicene conjugate), which was subsequently characterized at the molecular level in either an aqueous environment or an organic phase, at the supramolecular level in the form of polymeric layers, and also embedded in a lipidic mesophase environment to study the resulting properties of such a hybrid relative to its parent molecules. The flavin benzo[g]pteridin-2,4-dione (isoalloxazine) was selected for conjugation because of its photoactivity and reversible redox behavior. Compound 1 was prepared from 2-nitroso[6]helicene and 6-methylamino-3-methyluracil, and characterized using common structural and spectroscopic tools: circular dichroism (CD), circularly polarized luminescence (CPL) spectroscopy, cyclic voltammetry (CV), and DFT quantum calculations. In addition, a methodology that allows the loading of 1 enantiomers into an internally nanostructured lipid (1-monoolein) matrix was developed.
Identifiants
pubmed: 33977667
doi: 10.1002/cplu.202100092
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
982-990Subventions
Organisme : Institute of Chemical Process Fundamentals of the CAS
Organisme : Palacky University
ID : RVO 61989592
Organisme : Palacky University
ID : IGA_LF_2020_022
Organisme : Ministry of Education, Youth and Sports
Organisme : Czech Science Foundation
ID : 20-19353S
Organisme : Czech Science Foundation
ID : CZ.02.2.69/0.0/0.0/16_027/0008482
Organisme : Czech Science Foundation
ID : e-INFRA LM2018140
Informations de copyright
© 2021 Wiley-VCH GmbH.
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