Supramolecular structures based on regioisomers of cinnamyl-alpha-cyclodextrins - new media for capillary separation techniques

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10321852" target="_blank" >RIV/00216208:11310/16:10321852 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.3762/bjoc.12.11" target="_blank" >http://dx.doi.org/10.3762/bjoc.12.11</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3762/bjoc.12.11" target="_blank" >10.3762/bjoc.12.11</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Supramolecular structures based on regioisomers of cinnamyl-alpha-cyclodextrins - new media for capillary separation techniques

Popis výsledku v původním jazyce

This work focuses on the preparation and application of supramolecular structures based on mono-cinnamyl-a-cyclodextrins (Cin-alpha-CD). Pure regioisomers of Cin-alpha-CD having the cinnamyl moiety at the 2-O-or at the 3-O-position, respectively, were prepared, characterized and applied in capillary electrophoresis as additives to the background electrolyte. These new monomer units with a potential to self-organize into supramolecular structures were synthesized via a straightforward one-step synthetic procedure and purified using preparative reversed-phase chromatography allowing a large scale separation of the regioisomers. The ability of the monomers to self-assemble was proved by various methods including NMR spectroscopy and dynamic light scattering (DLS). The light scattering experiments showed that the monomer units have distinguishable ability to form supramolecular structures in different solvents and the size distribution of the aggregates in water can be easily modulated using different external stimuli, such as temperature or competitive guest molecules. The obtained results indicated that the two regioisomers of Cin-a-CD formed different supramolecular assemblies highlighting the fact that the position of the cinnamyl group plays an important role in the intermolecular complex formation.

Název v anglickém jazyce

Supramolecular structures based on regioisomers of cinnamyl-alpha-cyclodextrins - new media for capillary separation techniques

Popis výsledku anglicky

This work focuses on the preparation and application of supramolecular structures based on mono-cinnamyl-a-cyclodextrins (Cin-alpha-CD). Pure regioisomers of Cin-alpha-CD having the cinnamyl moiety at the 2-O-or at the 3-O-position, respectively, were prepared, characterized and applied in capillary electrophoresis as additives to the background electrolyte. These new monomer units with a potential to self-organize into supramolecular structures were synthesized via a straightforward one-step synthetic procedure and purified using preparative reversed-phase chromatography allowing a large scale separation of the regioisomers. The ability of the monomers to self-assemble was proved by various methods including NMR spectroscopy and dynamic light scattering (DLS). The light scattering experiments showed that the monomer units have distinguishable ability to form supramolecular structures in different solvents and the size distribution of the aggregates in water can be easily modulated using different external stimuli, such as temperature or competitive guest molecules. The obtained results indicated that the two regioisomers of Cin-a-CD formed different supramolecular assemblies highlighting the fact that the position of the cinnamyl group plays an important role in the intermolecular complex formation.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CB - Analytická chemie, separace

OECD FORD obor

—

Projekt

<a href="/cs/project/GA13-01440S" target="_blank" >GA13-01440S: Chirální supramolekulární polymery založené na derivatizovaných cyklodextrinech jako nové prostředí pro kapilární separační techniky</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Beilstein Journal of Organic Chemistry

ISSN

1860-5397

e-ISSN

—

Svazek periodika

12

Číslo periodika v rámci svazku

January

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

13

Strana od-do

97-109

Kód UT WoS článku

000368474200001

EID výsledku v databázi Scopus

2-s2.0-84962250344