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10 article(s) from Jindrich, Jindrich

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

Konstantin Lebedinskiy,
Volodymyr Lobaz and
Jindřich Jindřich

Full Research Paper
Published 25 Nov 2022

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1. Graphical Abstract
2. Scheme 1: The synthesis of 6^A-azido-6^A-deoxy-per-6-O-tert-butyldimethylsilyl-β-cyclodextrin.
  
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3. Scheme 2: The synthesis of β-cyclodextrin dimers with permethylated secondary rims.
  
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4. Scheme 3: The synthesis of β-cyclodextrin dimers with permethylated primary rims.
  
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5. Figure 1: The fragments of ¹H NOESY NMR spectra of 4 (a), 10 (b), and 9 (c) indicating the interaction betwee...
  
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6. Figure 2: The fragment of the ¹H NMR spectrum of compounds 9 (green); 10 (red); 12 (blue) representing the si...
  
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7. Figure 3: Other cyclodextrins that were used in the solubilization experiments with tetracene.
  
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8. Figure 4: The tetracene UV absorbance dependence on concentration at 476 nm.
  
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9. Figure 5: The relative concentrations of tetracene in DMSO solutions with hosts 4, 5, 10, 12, 13–18 referred ...
  
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10. Figure 6: "Tail-to-tail" (a) and "head-to-head" (b) orientation of two cyclodextrin moieties and primary-rim ...
  
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11. Figure 7: Isotherms of the titration of tetracene with "dimeric" CD solutions in DMSO at 298 K (circles – 10;...
  
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12. Figure 8: Isotherms of the titration of tetracene with "monomeric" CD solutions in DMSO at 298 K (circles – 16...
  
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Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

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Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

Attila Palágyi,
Jindřich Jindřich,
Juraj Dian and
Sophie Fourmentin

Full Research Paper
Published 28 Sep 2022

Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

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New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions

Iveta Chena Tichá,
Simona Hybelbauerová and
Jindřich Jindřich

Full Research Paper
Published 01 Apr 2019

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1. Graphical Abstract
2. Figure 1: Schematic cone-shaped (a) and structure representations (b) of α-CD (six glucopyranoside units) and...
  
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3. Figure 2: Common cinchona alkaloids (cinchonine, cinchonidine, quinine, quinidine).
  
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4. Scheme 1: CuAAC click reaction of propargylated cinchona alkaloids 3a–d with 6^I-azido-6^I-deoxy-α-CD (1) and 6^I...
  
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5. Scheme 2: CuAAC click reaction of per-Me-N₃-α-CD (6) or per-Me-N₃-β-CD (7) and propargylated cinchona alkaloi...
  
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6. Scheme 3: Synthesis of difunctionalized α-CD 11 with quinine moieties.
  
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7. Figure 3: Representative ¹H NMR spectrum of the non-methylated quinidine–α-CD derivative 4d.
  
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8. Figure 4: Representative ¹³C NMR spectrum and parts of the HMBC spectrum of the non-methylated quinidine–α-CD...
  
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9. Scheme 4: AAA reaction of MBH carbamate 12 catalyzed by the prepared CD derivatives 4a–d, 5a–d, 8a–d, 9a–d, 11...
  
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Beilstein J. Org. Chem. 2019, 15, 830–839, doi:10.3762/bjoc.15.80

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Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives

Iveta Tichá,
Gábor Benkovics,
Milo Malanga and
Jindřich Jindřich

Full Research Paper
Published 13 Nov 2018

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1. Graphical Abstract
2. Figure 1: Schematic representation of native α-CD (1) and top view of its primary rim with alphabetic clockwi...
  
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3. Scheme 1: Synthesis of 6^A,6^X-diazido-α-CD derivatives 4 via 6^A,6^X-capped α-CDs 2 and 3 and their regioisomeri...
  
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4. Scheme 2: Synthesis of 6^A,6^X- and 6^A,6^D-diazido-α-CDs via 6^A,6^X-dibromo-α-CD 5, 6^A,6^D-dibromo-α-CD 5d interme...
  
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5. Scheme 3: Synthesis of 6^A,6^X-diazido-α-CDs via 6^A,6^X-ditosyl-α-CD intermediates 6 and their regioisomeric rat...
  
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6. Figure 2: HPLC chromatograms of 6^A,6^X-diazido-α-CDs 4 of the reactions 1–5, with ACN/water gradient elution a...
  
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7. Scheme 4: Synthesis of 6^A-azido-6^X-mesitylenesulfonyl-α-CD 8 and conversion into 6^A,6^X-diazido-α-CD 4.
  
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8. Figure 3: HPLC chromatograms of reaction 7 with separated 6^A-azido-α-CD 7 as starting material and regioisome...
  
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9. Figure 4: HPLC chromatograms of 6^A-azido-6^X-mesitylenesulfonyl-α-CD 8 (reaction 6): a) analytical and b) prep...
  
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10. Figure 5: ¹H NMR spectrum of the AC regioisomer 8c as a mixture of pseudoenantiomers prepared through reactio...
  
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11. Figure 6: ¹³C NMR spectrum of the AC regioisomer 8c as a mixture of pseudoenantiomers prepared through reacti...
  
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12. Figure 7: HPLC–MS chromatogram with the separated pseudoenantiomers of 6^A-azido-6^B-mesitylenesulfonyl-α-CD 8b...
  
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Beilstein J. Org. Chem. 2018, 14, 2829–2837, doi:10.3762/bjoc.14.261

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Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

Markéta Bláhová,
Sergey K. Filippov,
Lubomír Kováčik,
Jiří Horský,
Simona Hybelbauerová,
Zdenka Syrová,
Tomáš Křížek and
Jindřich Jindřich

Full Research Paper
Published 27 Nov 2017

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1. Graphical Abstract
2. Scheme 1: Preparation of 2^I-O-, 3^I-O- and 6^I-O-naphthylallyl derivatives of γ-CD by cross-metathesis.
  
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3. Scheme 2: Preparation of 2-O-, 3-O- and 6-O-NA derivatives of γ-CD by direct alkylation (see Table 1 for the yields ...
  
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4. Figure 1: Volume-weighted distribution functions for water solutions of 2-O- (2a), 3-O- (2b), and 6-O- (2c) N...
  
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5. Figure 2: Distribution functions for 2-O- (2a), 3-O- (2b), and 6-O- (2c) NA-γ-CD regioisomers in 50% MeOH (v/...
  
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6. Figure 3: Volume-weighted distribution functions for the 3-O- (2b) and 6-O- (2c) NA-γ-CD regioisomer at diffe...
  
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7. Figure 4: Effect of increasing concentration and sonication on the morphology of the 3-O-derivative 2b. A to ...
  
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8. Figure 5: Effect of increasing concentration and sonication on the morphology of the 2-O-derivative 2a. A: 2 ...
  
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9. Figure 6: Effect of increasing concentration and sonication on the morphology of the 6-O-derivative 2c. A: 0....
  
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10. Figure 7: Heat change for injection per mole of NA-γ-CD added as a function of the total concentration of NA-...
  
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11. Figure 8: ¹H NMR spectra of 2-O-derivative 2a in D₂O at concentrations of 100, 10, and 1 mM.
  
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12. Figure 9: ¹H NMR spectra of 3-O-derivative 2b in D₂O at concentrations of 100, 10, and 1 mM.
  
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13. Figure 10: Putative objects and interactions in naphthylallyl-γ-CD solution, depicted schematically for 6^I-O-n...
  
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Beilstein J. Org. Chem. 2017, 13, 2509–2520, doi:10.3762/bjoc.13.248

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Optimized methods for preparation of 6^I-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives

Eva Bednářová,
Simona Hybelbauerová and
Jindřich Jindřich

Full Research Paper
Published 24 Feb 2016

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1. Graphical Abstract
2. Scheme 1: Synthesis of oligoethylene glycol dithiols.
  
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3. Scheme 2: Synthesis of β-cyclodextrinthiols and -disulfides.
  
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Beilstein J. Org. Chem. 2016, 12, 349–352, doi:10.3762/bjoc.12.38

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

Gabor Benkovics,
Ondrej Hodek,
Martina Havlikova,
Zuzana Bosakova,
Pavel Coufal,
Milo Malanga,
Eva Fenyvesi,
Andras Darcsi,
Szabolcs Beni and
Jindrich Jindrich

Full Research Paper
Published 19 Jan 2016

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1. Graphical Abstract
2. Figure 1: Example of elucidation of 2D NMR spectra of 2-O-Cin-α-CD.
  
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3. Figure 2: 2D ROESY spectrum of 2-O-Cin-α-CD in D₂O at 25 °C at 24 mM concentration.
  
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4. Figure 3: Expansion of the 2D ROESY spectrum of 2-O-Cin-α-CD indicating the geometric arrangement.
  
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5. Figure 4: ¹H NMR spectra of 2-O-Cin-α-CD in D₂O at 25 °C at different concentrations.
  
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6. Figure 5: ¹H NMR spectra of 3-O-Cin-α-CD in D₂O at 25 °C recorded at various concentrations.
  
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7. Figure 6: Diffusion coefficients of 2-O-Cin-α-CD (black) and, 3-O-Cin-α-CD (red) in D₂O at various concentrat...
  
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8. Figure 7: Effect of solvent on the size distribution of aggregates formed by 2-O-Cin-α-CD at 25 °C (the appli...
  
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9. Figure 8: Effect of a solvent on the size distribution of aggregates formed by 3-O-Cin-α-CD at 25 °C (the app...
  
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10. Figure 9: Aggregate sizes (diameter) of 2-O-Cin-α-CD (black) and 3-O-Cin-α-CD (red) in water at various tempe...
  
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11. Figure 10: Schematic representation of the DLS experiment proving the host–guest nature of the aggregate forma...
  
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12. Figure 11: The effect of competitive additives on the size distribution of aggregates formed by 3-O-Cin-α-CD a...
  
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13. Figure 12: Expansion of the 2D ROESY spectrum of 2-O-Cin-α-CD in the presence of CioOK as competitive guest mo...
  
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14. Figure 13: ¹H NMR spectrum of 2-O-Cin-α-CD before (up) and after (down) the addition of CioOK in 5-fold molar ...
  
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15. Figure 14: The influence of 5 mM 2-O-Cin-α-CD in BGE (right column) on the decrease of the effective electroph...
  
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Beilstein J. Org. Chem. 2016, 12, 97–109, doi:10.3762/bjoc.12.11

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

Martin Popr,
Sergey K. Filippov,
Nikolai Matushkin,
Juraj Dian and
Jindřich Jindřich

Full Research Paper
Published 02 Feb 2015

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1. Graphical Abstract
2. Scheme 1: Thermal decomposition of PEMEDA- and PEMPDA-β-CD with the decomposition products as characterized b...
  
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3. Figure 1: Decomposition kinetics of PEMEDA- and PEMPDA-β-CD at 50 °C as determined by ¹H NMR thermal experime...
  
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4. Scheme 2: Host and guest molecules employed in K_s determination in solution at different pH.
  
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5. Figure 2: Stability constants for β-CD with SAL, MEQ and NIA obtained by ITC measurements.
  
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6. Figure 3: Stability constants for PEMPDA-β-CD with SAL, MEQ and NIA obtained by ITC measurements.
  
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7. Scheme 3: Deposition of PEMPDA-β-CD onto solid surface (Nafion^® 117).
  
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8. Figure 4: Deposition kinetics of PEMPDA-β-CD onto Nafion^® 117 as obtained from ELSD detection of the decreasi...
  
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9. Scheme 4: Deposition of three model guests into the cavities of immobilized PEMPDA-β-CD.
  
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Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20

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

Martin Popr,
Simona Hybelbauerová and
Jindřich Jindřich

Full Research Paper
Published 18 Jun 2014

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1. Graphical Abstract
2. Figure 1: Schematic representation of the prepared sets of permanently charged CD derivatives.
  
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3. Scheme 1: Synthesis of monotrimethylammonio-CD derivatives.
  
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4. Scheme 2: Preparation of diamines 7 and 8 as reagents for further synthesis [29].
  
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5. Scheme 3: Synthesis of PEMEDA-CD derivatives.
  
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6. Scheme 4: Synthesis of PEMPDA-CD derivatives.
  
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7. Scheme 5: Synthesis of 1-azido-2-iodoethane.
  
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8. Scheme 6: Synthesis of azidoethane-containing derivatives of PEMEDA and PEMPDA-β-CD.
  
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9. Scheme 7: Synthesis of CD derivatives monosubstituted with a quaternary triamine moiety.
  
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Beilstein J. Org. Chem. 2014, 10, 1390–1396, doi:10.3762/bjoc.10.142

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Cross-metathesis of allylcarboranes with O-allylcyclodextrins

Ivan Šnajdr,
Zbyněk Janoušek,
Jindřich Jindřich and
Martin Kotora

Letter
Published 23 Nov 2010

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1. Graphical Abstract
2. Figure 1: Starting allylcarboranes 1a–1c and O-allylcyclodextrins 2a–2c.
  
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3. Scheme 1: Cross-metathesis of allylcarboranes 1 and O-allylcyclodextrins 2.
  
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Beilstein J. Org. Chem. 2010, 6, 1099–1105, doi:10.3762/bjoc.6.126

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