Martin Popr

Charles University

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Jindřich Jindřich

Charles University

Simona Hybelbauerová

Charles University

Pavel Coufal

Charles University

Gábor Benkovics

Budapest University of Technology and Economics

Květa Kalíková

Charles University

Zuzana Bosáková

Charles University

Sergey K. Filippov

DWI – Leibniz Institute for Interactive Materials

Martina Havlíková

Charles University

Hana Procházková

Charles University

Gabriela Kučerová

Universität Ulm

Cooperative Institutions

Charles University

Czech Academy of Sciences, Institute of Analytical Chemistry

Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Czech Academy of Sciences

Czech Academy of Sciences, Institute of Macromolecular Chemistry

Budapest University of Technology and Economics

CycloLab (Hungary)

University High School

DWI – Leibniz Institute for Interactive Materials

Åbo Akademi University

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Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives – their stability, complexation ability in solution or when deposited on solid anionic surface

Beilstein Journal of Organic Chemistry (2015)

Martin Popr Sergey K. Filippov Nikolai Matushkin J. Dian Jindřich Jindřich

The thermal stability of the monosubstituted cationic cyclodextrin (CD) derivatives PEMEDA-β-CD and PEMPDA-β-CD, which differ in their substituent linker length (ethylene and propylene, respectively), was studied via (1)H NMR experiments. PEMPDA-β-CD exhibited higher resistance towards the Hofmann degradation and was chosen as a more suitable host molecule for further studies. Inclusion properties of PEMPDA-β-CD in solution with a series of simple aromatic guests (salicylic acid, p-methoxyphenol and p-nitroaniline) were determined by isothermal titration calorimetry (ITC) and compared to the native β-CD. Permanently charged cationic CD derivatives were successfully deposited on the anionic solid surface of polymeric Nafion(®) 117 membrane via electrostatic interactions. Deposition kinetics and coverage of the surface were determined by ELSD. Finally, the ability of the CD derivatives bound to the solid surface to encapsulate aromatic compounds from aqueous solution was measured by UV-vis spectroscopy. The obtained results are promising for future industrial applications of the monosubstituted β-CD derivatives, because the preparation of cationic CD derivatives is applicable in large scale, without the need of chromatographic purification. Their ionic deposition on a solid surface is simple, yet robust and a straightforward process as well.

Cationic polymerization

10.3762/bjoc.11.20

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Citations (5)

Synthesis of 3I-O and 2I-O-monosubstituted derivatives of per-6-azido-β-cyclodextrin—potential molecular scaffolds

Carbohydrate Research (2012)

Martin Popr Simona Hybelbauerová Jindřich Jindřich

Propargyl bromide

Structural isomer

Allyl bromide

Propargyl

10.1016/j.carres.2012.09.003

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Citations (1)

Chromatographic Characterization of a New Cationic β-CD Based Stationary Phase Prepared by Dynamic Coating

Chromatographia (2016)

Gabriela Kučerová Květa Kalíková Hana Procházková Martin Popr Jindřich Jindřich

Cationic polymerization

Derivative (finance)

10.1007/s10337-016-3050-z

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Citations (8)

Synthesis of cyclodextrin derivatives for practical applications

Martin Popr

Source

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Citations (1)

Syntéza derivátů beta-cyklodextrinu pro medicinální aplikace

Martin Popr

BETA (programming language)

Source

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Citations (0)

Use of 6-O-mono-substituted derivatives of β-cyclodextrin-bearing substituent with two permanent positive charges in capillary electrophoresis

Chemical Papers (2016)

Martina Havlíková Zuzana Bosáková Gábor Benkovics Jindřich Jindřich Martin Popr

10.1515/chempap-2016-0053

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Citations (4)

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

Beilstein Journal of Organic Chemistry (2014)

Martin Popr Simona Hybelbauerová Jindřich Jindřich

An efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, β-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a substituent containing two cationic sites separated by an ethylene or a propylene linker were prepared by reacting mono-Ts-CD with neat N,N,N'-trimethylethane-1,2-diamine or N,N,N'-trimethylpropane-1,3-diamine and subsequent methylation by CH3I in good yields. Finally, analogues bearing a moiety with three tetraalkylammonium sites were synthesized by reacting mono-Ts-CD with bis(3-aminopropyl)amine and subsequent methylation. The majority of the presented reactions are very straightforward with a simple work-up, which avoids the need of chromatographic separation. Thus, these reactions are suitable for the multigram-scale production of monosubstituted cationic CDs.

Cationic polymerization

Moiety

Linker

10.3762/bjoc.10.142

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Citations (19)