Superstructures with cyclodextrins: Chemistry and applications
Cyclodextrins (CDs) are cyclic oligosaccharides consisting of 1,4-glycosidically linked α-D-glucose units. Production of these compounds is accomplished by enzymatic degradation of starch using CD-glycosyl transferase. Since their discovery more than 100 years ago, a significant development in CD research has taken place. Various applications of CDs can be found, e.g. the binding of odors and flavors. Even drugs can be complexed and set free after a while by CDs. This enables the transfer of hydrophobic substances into aqueous media, which is of great interest in pharmaceutical chemistry. Regarding the interactions of CDs with low-molecular and macromolecular compounds, respectively, the reactivity of complexed molecules is another key factor besides solubility effects.
See also the Thematic Series:
Superstructures with cyclodextrins: Chemistry and applications IV
Superstructures with cyclodextrins: Chemistry and applications III
Superstructures with cyclodextrins: Chemistry and applications II
- Letter
- Published 16 Aug 2012
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Scheme 1: Enantiodifferentiating photoisomerizations of 1Z and 2ZZ sensitized by β- and γ-cyclodextrin nanosp...
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Scheme 2: Representative enantiodifferentiating photosensitization of 1Z and 2ZZ with conventional and supram...
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Figure 1: (a) Circular dichroism spectra of 3 (67 μg/mL) (black), 4 (67 μg/mL) (red) and 5 (50 μg/mL) (blue) ...
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Figure 2: Circular dichroism spectra of 3 (67 μg/mL) (a) in water at pH 1.9 (black), 4.0 (red), 7.5 (green) a...
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- Published 16 Aug 2012
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Scheme 1: Structure of pAAmPy.
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Figure 1: Steady-state fluorescence spectra for 0.04 g L−1 pAAmPy at varying xDMSO from 0 to 1 with excitatio...
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Figure 2: Steady-state fluorescence spectra for 0.04 g L−1 pAAmPy with excitation at 335 nm in the presence o...
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Figure 3: I480/I376 as a function of [CD]0 for β-CD/pAAmPy (a) and γ-CD/pAAmPy (b) at different xDMSO.
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Scheme 2: Simplified equilibria of CDs/pAAmPy systems.
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Figure 4: KPy, Kβ, and Kγ as a function of xDMSO.
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- Published 16 Aug 2012
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Figure 1: Formation of and coalescence of a polymer sample from its crystalline cyclodextrin inclusion comple...
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Figure 2: Crystal structures and wide-angle X-ray diffractograms of neat (a) cage and (b) columnar IC γ-CD [20].
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Figure 3: DSC cooling scans of as-received (upper) and coalesced N-6 (lower) [58].
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Figure 4: DSC heating scans for asr-PVAc (upper) and c-PVAc coalesced from its γ-CD IC (lower) [72].
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Figure 5: Melt-crystallization curves of as-received and coalesced PCL observed at 20, 10, 5, and 1 °C/min co...
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Figure 6: X-ray diffraction patterns of as-synthesized PCL-b-PLLA films (a) and coalesced PCL-b-PLLA films (b...
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Figure 7: Polarizing photomicrographs of (a) PLLA, (b) PCL, (c) solution-cast, and (d) coalesced PLLA/PCL ble...
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Figure 8: X-ray diffractograms of (a) pure PCL and (b) PLLA and PCL/PLLA blends obtained by casting from diox...
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Figure 9: MDSC scans of the (a) first and (b) second heating runs recorded for the PC/PMMA/PVAc-2 blend. The ...
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Figure 10: Storage modulus, loss modulus, and apparent viscosity (G’, G’’, and n*, respectively) for asr- and ...
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Figure 11: Crystalline all trans (t) and γ-CD-included g±tg
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conformations of PET [76].
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Figure 12: DSC scans for p-PET [70].
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Figure 13: DSC cooling scans from the melts of (I) asr-N-6, (II) nuc-N-6, and (III) asr/nuc N-6 film sandwich....
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Figure 14: Mechanical properties of N-6 films [62].
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Figure 15: Tensile testing of as-received/as-received and as-received/nucleated nylon-6 film sandwiches conduc...
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- Published 06 Sep 2012
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Figure 1: Water-soluble phosphanes 1–4.
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Figure 2: 2D T-ROESY NMR spectrum of a stoichiometric mixture of β-CD and 4 (3 mM each) in D2O at 20 °C.
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Figure 3: Effect of increasing concentrations of β-CD (solid lines) and RAME-β-CD (dotted lines) on the surfa...
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Figure 4: Equilibria in a phosphane-based micelle/RAME-β-CD mixture.
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Scheme 1: Tsuji–Trost reaction mediated by a phosphane-based micelle/RAME-β-CD combination.
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Figure 5: Turnover frequency (TOF) as a function of the RAME-β-CD/phosphane ratio in the Pd-catalyzed cleavag...
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- Published 11 Sep 2012
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Scheme 1: Synthesis of PDOF-BT and PDOF-BTc copolymers.
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Figure 1: 1H NMR spectrum (CDCl3) of the BTc inclusion complex.
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Figure 2: FTIR spectra (KBr pellet) of PDOF-BT (A) and PDOF-BTc (B) copolymers.
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Figure 3: 1H NMR spectrum of PDOF-BT copolymer (CDCl3).
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Figure 4: 1H NMR spectrum of PDOF-BTc copolymer (CDCl3).
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Figure 5: DSC curves of BTc and PDOF-BTc from second-heating DSC measurements.
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Figure 6: Thermogravimetric curves (TG) for BTc, PDOF-BT, and PDOF-BTc compounds.
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Figure 7: High-resolution tapping-mode AFM images and cross-section plots (along the solid line in the images...
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- Published 13 Sep 2012
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Scheme 1: Mechanism of free radical ring-opening polymerization of 2-VCPs (In: initiator) [29-31].
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Scheme 2: Synthesis of diethyl 2-vinyl-1,1-cyclopropanedicarboxylate [33].
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Scheme 3: Two-step synthesis of the macromonomer 5 (In: Initiator, TEA: triethylamine).
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Figure 1: MALDI-TOF MS of amino-terminated poly(NiPAAm) 3.
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Figure 2: Optical transmittance of aqueous solutions (c = 20 mg/mL) of 3, 6 und 8 during heating.
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Figure 3: 2D ROESY NMR spectrum of a 5/Me2-β-CD deuterated water solution.
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Figure 4: Temperature-dependent transparency measurements of aqueous solution of the supramolecular complex 7...
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Scheme 4: Homo- and copolymerization of macromonomer 5.
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- Published 17 Sep 2012
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Figure 1: Mannose–adamantane conjugates 1–4 and amphiphilic cyclodextrin 5.
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Figure 2: Integrated peak area (left) and raw titration curves (right) for the ITC measurements of 1–4 with β...
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Figure 3: Schematic presentation of the binding between β-cyclodextrin and (A) monovalent guest 1, (B) divale...
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Figure 4: (A) Agglutination of β-cyclodextrin vesicles in the presence of monovalent guest 1 and ConA. The su...
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Figure 5: (A) Agglutination dependence of β-cyclodextrin vesicles in the presence of guests 2–4. Legend: red ...
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Figure 6: (A) Agglutination of β-cyclodextrin vesicles in the presence of guest 2 or 3 and ConA. Legend: red ...
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Figure 7: Schematic presentation of the binding of (A) a monovalent, (B) a divalent, or (C) a trivalent guest...
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Figure 8: (A) Agglutination of β-cyclodextrin vesicles in the presence of guest 2 or 4 and ConA. Legend: red ...
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Figure 9: Schematic presentation of the binding of guest molecules with (A) one or (B) two mannose functions ...
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- Published 20 Sep 2012
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Figure 1: Chemical structures of the CD dimer (α,α-CD dimer, α,β-CD dimer, and β,β-CD dimer) and guest deriva...
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Figure 2: Photographs of hydrogelation with various concentrations of α,α-CD dimer/VP in water. Aqueous solut...
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Figure 3: Hydrogelation of VP with various CD derivatives (VP unit/CD 4:1) at 25 °C. (a) Concentrations of CD...
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Figure 4: 500 MHz 1H NMR spectra of VP (VP unit 2 mM) with α-CD and PyC10Py (VP unit/CD/PyC10Py 1:2:8) in D2O...
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Figure 5: G' and G'' of the α,α-CD dimer/VP hydrogel as a function of frequency (ω). Applied shear strain amp...
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- Published 24 Sep 2012
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Scheme 1: Synthesis of PDMS-Im/Br ionic liquid.
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Figure 1: Appearance of (A) pure PDMS-Im/Br ionic liquid; (B) PDMS-Im/Br ionic liquid containing 1 wt % PRot.
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Figure 2: Wet-STEM images at 30 kV in bright field mode of: PDMS-Im/Br ionic liquid (A,B) and mixture of PDMS...
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Figure 3: Amplitude sweep results for PDMS-Im/Br and PDMS-Im/Br+PRot at 25 °C.
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Figure 4: Storage (G’) and loss (G”) moduli dependence on frequency for PDMS-Im/Br and PDMS-Im/Br+PRot at 25 ...
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Figure 5: Storage (G’) and loss (G”) moduli dependence on temperature for PDMS-Im/Br and PDMS-Im/Br+PRot.
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Figure 6: Flow curves for PDMS-Im/Br and PDMS-Im/Br + PRot at 25 °C.
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Figure 7: Temperature dependence of flow curves for PDMS-Im/Br ionic liquid.
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Figure 8: Temperature dependence of flow curves for PDMS-Im/Br+PRot.
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Figure 9: DSC second heating curves of: (1) PDMS-Im/Br ionic liquid, (2) mixture of PDMS-Im/Br with Prot and ...
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- Published 28 Sep 2012
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Figure 1: Space-filling model of the most stable complex between γ-CD and C60 with 1:2 stoichiometry, calcula...
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Scheme 1: Chemical structures of γ-CD and γ-CD thioether 1–7 used to solubilize C60 in water.
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Figure 2: UV–vis spectra of (a) C60 solution in THF, (b) aqueous solutions of C60 with 6 mM γ-CD thioether 5 ...
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Figure 3: Isothermal kinetics of the dissolution of C60 in the presence of 10 mM CD 7 in water. Curve: best f...
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Scheme 2: Mechanistic description of the two possible mechanisms for the complexation of C60 (G) by CD hosts,...
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Figure 4: Phase-solubility diagram of C60 in aqueous solution in the presence of CD 3.
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Figure 5: UV–vis spectra of the water solution of C60 produced by stirring C60 in 6mM γ-CD solution in DMF/to...
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Figure 6: Size distribution of the molecular solution of C60 with 6 mM CD 5 in water at 25.0 °C: before centr...
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Figure 7: Size distributions of the aqueous C60 dispersions after filtration, produced by stirring C60 in 6mM...
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- Published 01 Nov 2012
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Figure 1: AFM images of (a) Fe-Ni/Zn and (b) Fe-Ni/Zn/βCD.
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Figure 2: TEM images of (a) Fe-Ni/Zn and (b) Fe-Ni/Zn/βCD and SEM images of (c) Fe-Ni/Zn and (d) Fe-Ni/Zn/βCD....
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Figure 3: DLS measurements for before (a) and (b) and after (c) and (d) the sonication process.
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Figure 4: Potentiometric curves of the (a) Fe-Ni/Zn and (b) Fe-Ni/Zn/βCD.
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Figure 5: Zeta potential curves as a function of pH for the (○) Fe-Ni/Zn and (▲) Fe-Ni/Zn/βCD.
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Figure 6: Relative optical obscuration (Ob/Ob,0) as a function of time for (a) Fe-Ni/Zn and (b) Fe-Ni/Zn/βCD.
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Figure 7: Obscuration curves for the Fe-Ni/Zn (○) and Fe-Ni/Zn/βCD (▲) as a function of pH.
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Figure 8: Adsorption curves of (a) Cr3+ and (b) Cr2O72− ions using Fe-Ni/Zn and Fe-Ni/Zn/βCD aqueous suspensi...
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- Published 06 Nov 2012
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Figure 1: Structures of the methylated β-CD derivatives investigated.
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Figure 2: Temperature dependence of −TΔS°, ΔH° and ΔG° for the inclusion of 1-adamantane carboxylate in hepta...
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Figure 3: Structural drawing of β-CD [43], according to structural data (CSD-ID BUVSEQ03) from Zabel et al. [38], gen...
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- Published 14 Nov 2012
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Scheme 1: CTP of 1 and end-group functionalization with 5 yielding the azo-dye-end-group-labeled polymer 6.
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Figure 1: Absorption spectra of 6 in water in a pH range from 7 to 2 (A). Absorption spectra of 6 in water de...
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Figure 2: LCST measurements of 6, the complex of 6 and RAMEB-CD, and in comparison to pure PNIPAM.
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Figure 3: Hydrodynamic diameters of 6, 7 and 8 (1 mg/mL) at 20 °C.
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Figure 4: z-Average diameter (DZ) of the complex 8 in water as a function of temperature (0.5 mg/mL, heating ...
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- Published 29 Nov 2012
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Scheme 1: Synthetic routes to cyclodextrin nanosponges. (a) Cyclodextrin carbonate nanosponges. (b) Cyclodext...
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Figure 1: Molecular structure of cyclodextrin carbonate nanosponges.
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Figure 2: TEM microphotograph of cyclodextrin carbonate nanosponge (magnification 46,000×).
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- Published 04 Dec 2012
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Scheme 1: Synthetic pathway to the desired polymer 7.
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Figure 1: Cyclic voltammetry results of (A) clicked copolymer 7, (B) clicked copolymer 7 with Ad-COOK (
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).
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Figure 2: DLS measurement of compound 2 with β-cyclodextrin (— •), alkylated polyphenol 4 (- -), product 7 (—...
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- Published 13 Dec 2012
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Figure 1: Chemical structure of Triton® X-100 (1).
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Figure 2: Solubility in water of 0.2 wt % Triton® X-100 (1) and its different assumed complexes with RAMEB-CD...
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Scheme 1: Idealized reaction of the complexation of the (meth)acrylic monomer derived from Triton® (2 and 3) ...
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Scheme 2: Homopolymerization of the uncomplexed monomers 2 and 3 to the polymers 8 and 9 in DMF with AIBN as ...
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Scheme 3: Polymerization of the RAMEB-CD complexed monomers 4, 5, 6 and 7 to the homopolymers 10, 11, 12 and ...
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Figure 3: Transmittance [%] and zero-shear-viscosity [Pas] as a function of temperature for a 50 wt % solutio...
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- Published 17 Dec 2012
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Figure 1: Schematic representation of the β-cyclodextrin (a) and propiconazole (b) molecules.
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Figure 2: PM3 optimized molecular geometries of the β-CD/PP inclusion compounds involved in the assessment of...
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Figure 3: Molecular coordinates used to describe the relative position between the β-CD and guest molecules.
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Figure 4: Evolution of the stabilization energy during the movement along the z axis in the case of (a) A and...
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Figure 5: PM3 optimized molecular geometry of the β-CD/PP inclusion compounds in (a) A configuration and in (...
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Figure 6: AM1 optimized molecular geometry of the β-CD/PP inclusion compounds, for both (a) A and (b) B confi...
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Figure 7: Variation of the stabilization energy during the movement along the z axis, in the case of (a) A an...
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Figure 8: PM3 optimized molecular geometry of β-CD/PPH+ inclusion compounds in the (a) A and (b) B configurat...
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Figure 9: AM1 optimized molecular geometry of the inclusion compounds β-CD/PPH+ in the (a) A and (b) B config...
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Figure 10: MM+ optimized molecular geometry of the (a) β-CD/PP and (b) β-CD/PPH+ inclusion complexes, in both ...
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- Published 17 Jan 2013
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Figure 1: Chemical structure of fenitrothion (1).
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Figure 2: Representative TGA (top) and DSC (bottom) traces for DIMEB·1.
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Figure 3: The asymmetric unit in DIMEB•1 viewed along [010] (top) and [100] (bottom). H atoms are omitted for...
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Figure 4: The host molecules in the asymmetric unit of DIMEB·1 with the labelling of both residues and atoms ...
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Figure 5: The rotamers of 1 occupying the cavity of host molecule A. Common atoms have labels with suffix A, ...
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Figure 6: Stereoview of the three disordered guest components that occupy the cavity of host molecule B. Gues...
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Figure 7: Space-filling diagrams showing the relative orientations of guest molecules within the cavities of ...
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Figure 8: Packing diagrams of the DIMEB·1 structure, viewed along [100] (left) and [010] (right). The symmetr...
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Figure 9: Induced circular dichroism (a) and UV–vis (b) spectra of 1 in the presence of β-CD (10 mM, green), ...
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Scheme 1: Reaction of fenitrothion in basic media.
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Figure 10: Plot of kobs versus [DIMEB] for the hydrolysis reaction of fenitrothion with HO– at different conce...
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Scheme 2: Mechanism of the hydrolysis reaction of 1 mediated by DIMEB.
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- Published 18 Jan 2013
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Figure 1: Crystal structure of heptakis(6-O-triisopropylsilyl)-β-cyclodextrin benzene pyrene solvate; [C105H2...
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Figure 2: The two AM1-optimised stable conformers of BCDO23rO6l with benzene in a parallel (a and b) and vert...
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Figure 3: (a) AM1 calculated IR spectra of BCDO23rO6l empty and (b) the BCDO23rO6l/benzene inclusion complex ...
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Figure 4: The lowest energy empty conformer BCDO23rO6l, COSMO-RS structure optimised with BP/TZVP-DISP3 (solv...
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Figure 5: The lowest energy complex conformer BCDO23rO6l/benzene; benzene occupies an oblique position inside...
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Figure 6: σ-Profiles of the COSMO-RS method for the four empty β-CD models and benzene (BP/TZVP-DISP3 method)....
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Figure 7: σ-Potentials of the COSMO-RS method for the four empty β-CD models and benzene (BP/TZVP-DISP3 metho...
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Figure 8: a: BCDcry (MD starting structure with Compass-Etot = 389.99 kcal mol−1 and 14 hydrogen bonds with a...
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Figure 9: a: BCDO23rO6l (MD starting structure with Compass-Etot = 221.52 kcal mol−1 and 28 hydrogen bonds wi...
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Figure 10: a: BCDO23rO6r (MD starting structure with Compass-Etot = 217.25 kcal mol−1 and 28 hydrogen bonds wi...
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Figure 11: Distance plots from the MD trajectories of 500 ps each (x axis) for β-CD/benzene complex at differe...
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Figure 12: Three structures from the MD trajectory at 300 K: a: benzene left the β-CD at the O23 side; b: β-CD...
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Figure 13: β-CD/benzene complex energy diagram (Forcite analysis – Hamiltonian) of the MD trajectory at 290 K.
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- Published 29 Apr 2013
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Scheme 1: Synthesis of fluorescent cyclodextrin 3 by click-chemistry.
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Figure 1: 1H NMR-ROESY spectrum of the modified CD 3.
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Figure 2: UV–vis spectrum of 3 (4 × 10−4 M) with and without a 10-fold excess of potassium adamantane-1-carbo...
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Figure 3: Fluorescence spectrum of 3 (4 × 10−4 M) with and without a 10-fold excess of 1-adamantanecarboxylic...
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Figure 4: DLS measurement of 3 with and without a 10-fold excess of potassium adamantane-1-carboxylate; black...
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Figure 5: AF4 elution diagram of 3.
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- Published 19 Jun 2013
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Figure 1: Chemical structures of β-CD 1, hydroxypropyl-β-CD 2, and β-CD-thioethers 3 and 4.
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Figure 2: Chemical structures of the benzene and cyclohexane derivatives, with their calculated molecular vol...
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Figure 3: Chromatogram obtained by HS-GC for a mixture of aromatic guests (1 ppm) in water (black) and 10 mM ...
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Figure 4: Gibbs free energy of formation of the inclusion compound of benzene derivatives, and cyclohexane de...
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Figure 5: Gibbs free energy of formation of the inclusion compounds of benzene and cyclohexane derivatives in...
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Figure 6: Gibbs free energy of formation of the inclusion compounds of benzene derivatives in host 4 as a fun...
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Figure 7: Free binding enthalpy for benzene, toluene, ethylbenzene, cumene, and tert-butylbenzene, in host 4 ...
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Scheme 1: Hydrosilylation of Si–H terminated poly(dimethylsiloxanes) 1 and 2 with mono-((6-N-(allylamino)-6-d...
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Figure 1: IR spectra of (a) H-terminated disiloxane (1), (b) α-CD-terminated disiloxane (α-CD-disiloxane) (4)...
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Figure 2: 1H NMR spectra of ferrocene (A), complex of α-CD-disiloxane (α-CD-DS) 4 with ferrocene (B) and comp...
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Figure 3: 2D ROESY NMR spectra of the complex of α-CD-disiloxane (α-CD-DS) 4 with ferrocene.
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Figure 4: 2D ROESY NMR spectra of the complex of α-CD-polydimethylsiloxane (α-CD-PDMS) 5 with ferrocene.
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Figure 5: TEM images of α-CD-disiloxane 4 (A) and the supramolecular formation of α-CD-disiloxane 4 with ferr...
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Figure 6: DLS measurements of α-CD-disiloxane 4 (A) (dashed line) and the supramolecular formation of α-CD-di...
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- Published 12 Sep 2013
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Figure 1: Chemical structures of selected aromatic guests: anthracene, ANT; acenaphthylene, ACE; and coumarin...
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Figure 2: Structures of γ-CD and γ-CD thioethers 1–7.
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Scheme 1: Photodimerization of ACE.
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Figure 3: 1H NMR spectrum of the photo product of ACE in the presence of γ-CD thioether 3 in CDCl3.
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Figure 4: Schematic drawing of the ACE photodimers in γ-CD: a) the syn photodimer and b) the anti photodimer....
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Figure 5: Structures of COU photodimers.
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Figure 6: Partial 1H NMR of the photodimers formed after irradiation of COU at various concentrations of Na2SO...
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Scheme 1: Synthesis of the monomers 5 and 7, as well as the chemical structure of the diepoxide 8, comprising...
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Figure 1: Heating curves of the LCST measurements of 9, the complex of 9 with RAMEB-CD 9β, and of 9 with RAME...
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Figure 2: LCST measurements of 10 with illustrated heating and cooling curve, as well as the heating curve af...
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Figure 3: 2D NMR ROESY (300 MHz, D2O) spectrum of the complex of 5 with RAMEB-CD (a), displaying the correlat...
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Figure 4: Oscillatory rheological measurements of the curing of 9 and 10, respectively at 25 °C. Illustrated ...
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Figure 5: Illustration of the viscosity of a mixture of 5 and 8 (a), respectively 7 and 8 (c) before curing a...
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Figure 6: Comparison of the FTIR spectra of the monomer mixture of 5 and 8 and of the cured product 9 after 2...
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- Published 09 Dec 2013
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Scheme 1: Synthesis of sulfonamide 3, N-alkylation of 3 in organic solution and of CD-complex (3β) in aqueous...
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Figure 1: 2D NMR ROESY spectrum of the complex of 3 with β-CD in D2O, displaying the interaction of the tosyl...
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Scheme 2: Cyclization of L-(+)-lysine monohydrochloride to give racemate 8.
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Figure 2: Oscillatory rheological measurements of an equimolar mixture of 6 and 8 at 50 °C. Illustrated is th...
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