New synthetic strategies for xanthene-dye-appended cyclodextrins

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10323637" target="_blank" >RIV/00216208:11310/16:10323637 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.3762/bjoc.12.53" target="_blank" >http://dx.doi.org/10.3762/bjoc.12.53</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3762/bjoc.12.53" target="_blank" >10.3762/bjoc.12.53</a>

Jazyk výsledku

angličtina

Název v původním jazyce

New synthetic strategies for xanthene-dye-appended cyclodextrins

Popis výsledku v původním jazyce

Xanthene dyes can be appended to cyclodextrins via an ester or amide bridge in order to switch the fluorescence on or off. This is made possible through the formation of nonfluorescent lactones or lactams as the fluorophore can reversibly cyclize. In this context we report a green approach for the synthesis of switchable xanthene-dye-appended cyclodextrins based on the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). By using 6-monoamino-beta-cyclodextrin and commercially available inexpensive dyes, we prepared rhodamine-and fluorescein-appended cyclodextrins. The compounds were characterized by NMR and IR spectroscopy and MS spectrometry, their UV-vis spectra were recorded at various pH, and their purity was determined by capillary electrophoresis. Two potential models for the supramolecular assembly of the xanthene-dye-appended cyclodextrins were developed based on the set of data collected by the extensive NMR characterization.

Název v anglickém jazyce

New synthetic strategies for xanthene-dye-appended cyclodextrins

Popis výsledku anglicky

Xanthene dyes can be appended to cyclodextrins via an ester or amide bridge in order to switch the fluorescence on or off. This is made possible through the formation of nonfluorescent lactones or lactams as the fluorophore can reversibly cyclize. In this context we report a green approach for the synthesis of switchable xanthene-dye-appended cyclodextrins based on the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). By using 6-monoamino-beta-cyclodextrin and commercially available inexpensive dyes, we prepared rhodamine-and fluorescein-appended cyclodextrins. The compounds were characterized by NMR and IR spectroscopy and MS spectrometry, their UV-vis spectra were recorded at various pH, and their purity was determined by capillary electrophoresis. Two potential models for the supramolecular assembly of the xanthene-dye-appended cyclodextrins were developed based on the set of data collected by the extensive NMR characterization.

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

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

neuvedeno

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

12

Strana od-do

537-548

Kód UT WoS článku

000372535900001

EID výsledku v databázi Scopus

2-s2.0-84961997760