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Search for "inclusion properties" in Full Text gives 11 result(s) in Beilstein Journal of Organic Chemistry.
Reversible end-to-end assembly of selectively functionalized gold nanorods by light-responsive arylazopyrazole–cyclodextrin interaction
- Maximilian Niehues,
- Patricia Tegeder and
- Bart Jan Ravoo
Beilstein J. Org. Chem. 2019, 15, 1407–1415, doi:10.3762/bjoc.15.140
- photophysical properties like nearly quantitative isomerization, straight forward synthesis in excellent yields and very long Z-isomer half-life times up to 1000 days due to less steric repulsion [37]. In previous reports we could show that the AAP guest inclusion properties to β-CD are comparable to
Graphical Abstract
Scheme 1: Light-responsive end-to-end assembly of host-functionalized gold nanorods (AuNR) by cyclodextrin–AA...
Scheme 2: Two-step ligand exchange reaction for the synthesis of water-soluble cyclodextrin end-functionalize...
Figure 1: a) ζ-Potential measurement of different stages of the ligand exchange. b) UV–vis spectroscopy befor...
Figure 2: UV–vis spectroscopy of a) [tCD+tTEG]AuNR with different amount of dAAP (0-35 µM). b) [tCD]AuNR with...
Figure 3: SPR maxima of [tCD+tTEG]AuNR with dAAP during four cycles of irradiation. a) Longitudinal SPR. b) T...
Figure 4: TEM-BF images of a) [tCD+tTEG]AuNR. b and c) AuNR end-to-end assemblies by dAAP (15 µM). d) Dissolv...
Figure 5: Reversible aggregation of [tCD+tTEG]AuNR by addition of dAAP (15 µM) monitored by dynamic light sca...
Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study
- Valya K. Nikolova,
- Cristina V. Kirkova,
- Silvia E. Angelova and
- Todor M. Dudev
Beilstein J. Org. Chem. 2019, 15, 1321–1330, doi:10.3762/bjoc.15.131
- calixarenes (with the same repeating units). The sulfur functionalities are stated to provide better metal complexation [3]. Unmodified calixarenes and thiacalixarenes are sparingly soluble, have chemical and thermal stability and act as host molecules as they possess cavities, but their inclusion properties
Graphical Abstract
Scheme 1: Schematic representation of the structures of p-sulfonatocalix[4]arene (C[4]A) and p-sulfonatothiac...
Figure 1: Optimized structures of negatively charged C[4]A and TC[4]A, presented in two projections: (A) side...
Figure 2: Optimized structures of C[4]A complexes with Na+, Mg2+ and La3+.
Figure 3: Optimized structures of C[4]A complexes with Rb+, Sr2+ and Lu3+.
Figure 4: Optimized structures of TC[4]A complexes with Na+, Mg2+ and La3+.
Figure 5: Optimized structures of TC[4]A complexes with Rb+, Sr2+ and Lu3+.
Figure 6: M062X/6-31G(d,p) optimized structures of the [La(H2O)9]3+ cation, C[4]A host and C[4]A complex with...
Recent applications of chiral calixarenes in asymmetric catalysis
- Mustafa Durmaz,
- Erkan Halay and
- Selahattin Bozkurt
Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117
- results clearly confirmed the cooperative effect and special role of the calixarene backbone. Aldol reaction Since chiral substituents and binding sites attached to the upper rim of the calixarene backbone can offer the full advantage of the unique inclusion properties of hydrophobic cavity, Wang et al
Graphical Abstract
Figure 1: Inherently chiral calix[4]arene-based phase-transfer catalysts.
Scheme 1: Asymmetric alkylations of 3 catalyzed by (±)-1 and (±)-2 under phase-transfer conditions.
Scheme 2: Synthesis of chiral calix[4]arene-based phase-transfer catalyst 7 and structure of O’Donnell’s N-be...
Scheme 3: Asymmetric alkylation of glycine derivative 3 catalyzed by calixarene-based phase-transfer catalyst ...
Figure 2: Calix[4]arene-amides used as phase-transfer catalysts.
Scheme 4: Phase-transfer alkylation of 3 catalyzed by calixarene-triamide 12.
Scheme 5: Synthesis of inherently chiral calix[4]arenes 20a/20b substituted at the lower rim. Reaction condit...
Scheme 6: Asymmetric Henry reaction between 21 and 22 catalyzed by 20a/20b.
Figure 3: Proposed transition state model of asymmetric Henry reaction.
Scheme 7: Synthesis of enantiomerically pure phosphinoferrocenyl-substituted calixarene ligands 27–29.
Scheme 8: Asymmetric coupling reaction of aryl boronates and aryl halides in the presence of calixarene mono ...
Scheme 9: Asymmetric allylic alkylation in the presence of calix[4]arene ligand (S,S)-29.
Figure 4: Structure of inherently chiral oxazoline calix[4]arenes applied in the palladium-catalyzed Tsuji–Tr...
Scheme 10: Asymmetric Tsuji–Trost reaction in the presence of calix[4]arene ligands 36–39.
Figure 5: BINOL-derived calix[4]arene-diphosphite ligands.
Scheme 11: Asymmetric hydrogenation of 41a and 41b catalyzed by in situ-generated catalysts comprised of [Rh(C...
Figure 6: Inherently chiral calix[4]arene 43 containing a diarylmethanol structure.
Scheme 12: Asymmetric Michael addition reaction of 44 with 45 catalyzed by 43.
Figure 7: Calix[4]arene-based chiral primary amine–thiourea catalysts.
Scheme 13: Asymmetric Michael addition of 48 with 49 catalyzed by 47a and 47b.
Scheme 14: Enantioselective Michael addition of 51 to 52 catalyzed by calix[4]arene thioureas.
Scheme 15: Synthesis of calix[4]arene-based tertiary amine–thioureas 54–56.
Scheme 16: Asymmetric Michael addition of 34 and 57 to nitroalkenes 49 catalyzed by 54b.
Scheme 17: Synthesis of p-tert-butylcalix[4]arene bis-squaramide derivative 64.
Scheme 18: Asymmetric Michael addition catalyzed by 64.
Scheme 19: Synthesis of chiral p-tert-butylphenol analogue 68.
Figure 8: Novel prolinamide organocatalysts based on the calix[4]arene scaffold.
Scheme 20: Asymmetric aldol reactions of 72 with 70 and 71 catalyzed by 69b.
Scheme 21: Synthesis of p-tert-butylcalix[4]arene-based chiral organocatalysts 75 and 78 derived from L-prolin...
Scheme 22: Synthesis of upper rim-functionalized calix[4]arene-based L-proline derivative 83.
Scheme 23: Synthesis and proposed structure of Calix-Pro-MN (86).
Figure 9: Calix[4]arene-based L-proline catalysts containing ester, amide and acid units.
Scheme 24: Synthesis of calix[4]arene-based prolinamide 92.
Scheme 25: Calixarene-based catalysts for the aldol reaction of 21 with 70.
Scheme 26: Asymmetric aldol reactions of 72 with cyclic ketones catalyzed by calix[4]arene-based chiral organo...
Figure 10: A proposed structure for catalyst 92 in H2O.
Scheme 27: Synthetic route for organocatalyst 98.
Scheme 28: Asymmetric aldol reactions catalyzed by 99.
Figure 11: Proposed catalytic environment for catalyst 99 in the presence of water.
Scheme 29: Asymmetric aldol reactions between 94 and 72 catalyzed by 55a.
Scheme 30: Enantioselective Biginelli reactions catalyzed by 69f.
Scheme 31: Synthesis of calix[4]arene–(salen) complexes.
Scheme 32: Enantioselective epoxidation of 108 catalyzed by 107a/107b.
Scheme 33: Synthesis of inherently chiral calix[4]arene catalysts 111 and 112.
Scheme 34: Enantioselective MPV reduction.
Scheme 35: Synthesis of chiral calix[4]arene ligands 116a–c.
Scheme 36: Asymmetric MPV reduction with chiral calix[4]arene ligands.
Scheme 37: Chiral AlIII–calixarene complexes bearing distally positioned chiral substituents.
Scheme 38: Asymmetric MPV reduction in the presence of chiral calix[4]arene diphosphites.
Scheme 39: Synthesis of enantiomerically pure inherently chiral calix[4]arene phosphonic acid.
Scheme 40: Asymmetric aza-Diels–Alder reactions catalyzed by (cR,pR)-121.
Scheme 41: Asymmetric ring opening of epoxides catalyzed by (cR,pR)-121.
Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays
- Marco Russo,
- Daniele La Corte,
- Annalisa Pisciotta,
- Serena Riela,
- Rosa Alduina and
- Paolo Lo Meo
Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271
- inclusion properties of the main CD scaffold. At the same time, we wanted to clarify the microscopic features and quantitative aspects of the interaction between AmCDs and polyanions such as polynucleotides. For these purposes, we investigated by means of polarimetry the behaviour of materials CD1–CD3
Graphical Abstract
Figure 1: Structures of: a) AmCDs CD1–3; b) p-nitroaniline guests 1–4; c) sodium alginate (Alg).
Figure 2: Trends of the molar optical rotation Θ of AmCDs CD1–3 vs pH.
Figure 3: Trends of the molar optical rotation Θ of AmCDs vs χH+.
Figure 4: Polarimetric data trends for the inclusion of 4 in CD1 at different pH values.
Figure 5: Possible association of AmCDs with guests 2–4.
Figure 6: Polarimetric data trends for the CD1–Alg interaction (with buffer).
Figure 7: nr Values for the AmCD–Alg interaction as a function of <nH+>.
Figure 8: Electrophoretic mobility shift assays of pDNA in the presence of AmCDs at different N/P ratios, as ...
Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds
- Sophie Letort,
- Michaël Bosco,
- Benedetta Cornelio,
- Frédérique Brégier,
- Sébastien Daulon,
- Géraldine Gouhier and
- François Estour
Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45
- hydrolyze the organophosphorus (OP) compounds under physiological conditions. In this context, cyclodextrins (CD) constitute attractive starting materials because, due to the inclusion properties of their internal cavity, they can form host–guest complexes in aqueous media by weak interactions with small
Graphical Abstract
Figure 1: Structures of G agents.
Figure 2: Scavenger based on a heterodifunctionalized β-cyclodextrin derivative.
Figure 3: Structures of β-cyclodextrin derivatives 2–5.
Figure 4: Structures of pesticides tested.
Scheme 1: Synthetic pathway to derivatives 2 and 3 (Tr = trityl).
Scheme 2: Synthesis of compound 4.
Scheme 3: Synthesis of compound 5 (Tr = trityl).
Figure 5: Hydrolysis of methyl paraoxon (0.5 mM) in the presence of compounds 1, 2, 3 or 2-iodosobenzoic acid...
Figure 6: Hydrolysis of methyl paraoxon (0.5 mM) in the presence of compounds 1, 2, 3 or 2-iodosobenzoic acid...
Figure 7: Hydrolysis of methyl paraoxon (0.5 mM) in the presence of compounds 2, 4, 5 or 2-iodosobenzoic acid...
Figure 8: Hydrolysis of methyl paraoxon (0.5 mM) in the presence of mixtures of compounds 4, 5 with IBA or im...
Figure 9: Influence of the pesticide structure on the hydrolytic efficiency of compound 2 (0.25 mM). Kinetic ...
Figure 10: Influence of TRIMEB, IBA and imidazole on the hydrolysis of methyl parathion (0.5 mM). The final co...
Figure 11: Ability of compounds 1–4 in preventing the inhibition of acetylcholinesterase by soman (GD).
Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds
- Sophie Letort,
- Sébastien Balieu,
- William Erb,
- Géraldine Gouhier and
- François Estour
Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23
- degradation of tabun (Scheme 4) [80]. However, it should be pointed out that a simple glucose derivative bearing the same nucleophilic group has a similar activity. The efficiency of 20c is therefore clearly related to the pyridinium oxime functional group and not to the inclusion properties of the
Graphical Abstract
Figure 1: Structure of NOPs.
Figure 2: Examples of structures of NOPs.
Figure 3: Structures of pesticides studied in the literature as guest to form an inclusion complex with CDs.
Figure 4: Structures of pesticides sensitive to the presence of CDs.
Scheme 1: The hydrolysis mechanism of substrate (S) in presence of a cyclodextrin (CD).
Figure 5: Structures of the different stereoisomers of G agents.
Scheme 2: Reaction mechanism of CD accelerated decomposition of organophosphorus compound (PX).
Scheme 3: Proposed degradation mechanism of cyclosarin by β-CD [72].
Figure 6: Schematic representations of β-CD and TRIMEB.
Scheme 4: Synthetic pathways to 6-monosubstituted CD derivatives.
Scheme 5: Synthetic pathways to 2-monosubstituted CD by an iodosobenzoate group.
Scheme 6: Synthetic pathways to 2-monosubstituted CDs with N–OH derivatives.
Scheme 7: Synthetic pathways to 3-monosubstituted CDs.
Scheme 8: Synthetic pathways to 3-homodisubstituted CDs.
Scheme 9: Synthetic pathways to 2,3-heterodisubstituted CDs.
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
Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20
- PEMPDA-β-CD, which differ in their substituent linker length (ethylene and propylene, respectively), was studied via 1H 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
- , yet robust and a straightforward process as well. Keywords: cyclodextrins; inclusion properties; solid surface; tetraalkylammonium derivatives; thermal stability; Introduction Cyclodextrins (CDs) are a very interesting group of natural macrocyclic carbohydrates, which were first described by
- . Based on these results the PEMPDA-β-CD was selected for further measurements. Inclusion properties of PEMPDA-β-CD in solution To evaluate the ability of the cationic derivative PEMPDA-β-CD to form inclusion complexes in aqueous solution, we measured the stability constants (Ks) with three model aromatic
Graphical Abstract
Scheme 1: Thermal decomposition of PEMEDA- and PEMPDA-β-CD with the decomposition products as characterized b...
Figure 1: Decomposition kinetics of PEMEDA- and PEMPDA-β-CD at 50 °C as determined by 1H NMR thermal experime...
Scheme 2: Host and guest molecules employed in Ks determination in solution at different pH.
Figure 2: Stability constants for β-CD with SAL, MEQ and NIA obtained by ITC measurements.
Figure 3: Stability constants for PEMPDA-β-CD with SAL, MEQ and NIA obtained by ITC measurements.
Scheme 3: Deposition of PEMPDA-β-CD onto solid surface (Nafion® 117).
Figure 4: Deposition kinetics of PEMPDA-β-CD onto Nafion® 117 as obtained from ELSD detection of the decreasi...
Scheme 4: Deposition of three model guests into the cavities of immobilized PEMPDA-β-CD.
Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs
- Lisa F. Becker,
- Dennis H. Schwarz and
- Gerhard Wenz
Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310
- heating device from Harrick, Pleasantville, New York. The inclusion properties of the host molecules were investigated by head space gas chromatography with a Shimadzu GC-17A GC equipped with a head space unit from Shimadzu, Kyoto, Japan. Vials of 5 mL volume were used, the ratio between gas (V = 3.2 mL
Graphical Abstract
Scheme 1: Synthetic route to neutral water-soluble CD thioethers.
Figure 1: ESI MS spectra of CD derivatives 2b1 (left) and 3b1 (right).
Figure 2: 1H NMR spectra of a) the statistical CD derivatives 2b1 and b) the corresponding uniform derivative ...
Figure 3: Transmission (λ = 670 nm) of aqueous solutions (1.0 wt %) of 2b1 (red) and 3b1 (blue).
Figure 4: Decay of the relative vapour pressure A/A0 as function of the host concentration 3b1 measured by GC...
Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer
- Florian Hamon,
- Claire Blaszkiewicz,
- Marie Buchotte,
- Estelle Banaszak-Léonard,
- Hervé Bricout,
- Sébastien Tilloy,
- Eric Monflier,
- Christine Cézard,
- Laurent Bouteiller,
- Christophe Len and
- Florence Djedaini-Pilard
Beilstein J. Org. Chem. 2014, 10, 2874–2885, doi:10.3762/bjoc.10.304
- configurations, respectively. In these conditions, using azobenzene as a linker between two β-CD can lead to a modulation of the inclusion properties, such as a cooperative effect. The cavity of each CD is available to form an inclusion complex with a hydrophobic guest molecule. Among these, adamantane is known
Graphical Abstract
Scheme 1: Synthesis pathway of the dimer AZO-CDim 1.
Figure 1: Overlaid UV spectra of the irradiation of AZO-CDim 1 (a) from 0 to 120 min at 365 nm and then (b) f...
Figure 2: HPLC quantification of the cis/trans ratio of AZO-CDim 1 before irradiation (left) and after irradi...
Figure 3: Percentage of cis isomer of AZO-CDim 1 produced during photoisomerization cycles (c = 10−4 M, water...
Figure 4: Representation of the most stable structures obtained for the azobenzene linker (a) for the trans c...
Figure 5: Structure of the ditopic guest ADAdim 4.
Figure 6: Titration of (a) β-CD (c = 0.8 mM) and (b) β-CD-NH2 (c = 0.8 mM) by ADAdim 4 (c = 4 mM). (c) Diluti...
Figure 7: (a) 1H NMR spectra of AZO-CDim 1 (500 MHz, D2O, 2.5 mM) in the absence (bottom) and presence of ADA...
Figure 8: Proposed structures of inclusion complexes with the ditopic host AZO-CDim 1 and the ditopic guest A...
Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene
- Wenting Liang,
- Cheng Yang,
- Masaki Nishijima,
- Gaku Fukuhara,
- Tadashi Mori,
- Andrea Mele,
- Franca Castiglione,
- Fabrizio Caldera,
- Francesco Trotta and
- Yoshihisa Inoue
Beilstein J. Org. Chem. 2012, 8, 1305–1311, doi:10.3762/bjoc.8.149
- spectra shifting to higher wavenumbers. On the other hand, the stiffness of the polymeric network of CDNSs is more affected by the PMA/CD ratio, rather than the type of CD used. The adsorption, absorption and inclusion properties of these new materials have been demonstrated for a large variety of
Graphical Abstract
Scheme 1: Enantiodifferentiating photoisomerizations of 1Z and 2ZZ sensitized by β- and γ-cyclodextrin nanosp...
Scheme 2: Representative enantiodifferentiating photosensitization of 1Z and 2ZZ with conventional and supram...
Figure 1: (a) Circular dichroism spectra of 3 (67 μg/mL) (black), 4 (67 μg/mL) (red) and 5 (50 μg/mL) (blue) ...
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...
Molecular recognition of organic ammonium ions in solution using synthetic receptors
- Andreas Späth and
- Burkhard König
Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32
Graphical Abstract
Figure 1: Biologically important amines and quaternary ammonium salts: histamine (1), dopamine (2) and acetyl...
Figure 2: Crown ether 18-crown-6.
Figure 3: Conformations of 18-crown-6 (4) in solvents of different polarity.
Figure 4: Binding topologies of the ammonium ion depending on the crown ring size.
Figure 5: A “pseudorotaxane” structure consisting of 24-crown-8 and a secondary ammonium ion (5); R = Ph.
Figure 6: Typical examples of azacrown ethers, cryptands and related aza macrocycles.
Figure 7: Binding of ammonium to azacrown ethers and cryptands [111-113].
Figure 8: A 19-crown-6-ether with decalino blocking groups (11) and a thiazole-dibenzo-18-crown-6-ether (12).
Figure 9: 1,3-Bis(6-oxopyridazin-1-yl)propane derivatives 13 and 14 by Campayo et al.
Figure 10: Fluorescent azacrown-PET-sensors based on coumarin.
Figure 11: Two different pyridino-cryptands (17 and 18) compared to a pyridino-crown (19); chiral ammonium ion...
Figure 12: Pyridino-18-crown-6 ligand (21), a similar acridino-18-crown-6 ligand (22) and a structurally relat...
Figure 13: Ciral pyridine-azacrown ether receptors 24.
Figure 14: Chiral 15-crown-5 receptors 26 and an analogue 18-crown-6 ligand 27 derived from amino alcohols.
Figure 15: C2-symmetric chiral 18-crown-6 amino alcohol derivatives 28 and related macrocycles.
Figure 16: Macrocycles with diamide-diester groups (30).
Figure 17: C2-symmetric chiral aza-18-crown-6 ethers (31) with phenethylamine residues.
Figure 18: Chiral C-pivot p-methoxy-phenoxy-lariat ethers.
Figure 19: Chiral lariat crown ether 34.
Figure 20: Sucrose-based chiral crown ether receptors 36.
Figure 21: Permethylated fructooligosaccharide 37 showing induced-fit chiral recognition.
Figure 22: Biphenanthryl-18-crown-6 derivative 38.
Figure 23: Chiral lariat crown ethers derived from binol by Fuji et al.
Figure 24: Chiral phenolic crown ether 41 with “aryl chiral barriers” and guest amines.
Figure 25: Chiral bis-crown receptor 43 with a meso-ternaphthalene backbone.
Figure 26: Chromogenic pH-dependent bis-crown chemosensor 44 for diamines.
Figure 27: Triamine guests for binding to receptor 44.
Figure 28: Chiral bis-crown phenolphthalein chemosensors 46.
Figure 29: Crown ether amino acid 47.
Figure 30: Luminescent receptor 48 for bis-alkylammonium guests.
Figure 31: Luminescent CEAA (49a), a bis-CEAA receptor for amino acids (49b) and the structure of lysine bindi...
Figure 32: Luminescent CEAA tripeptide for binding small peptides.
Figure 33: Bis crown ether 51a self assembles co-operatively with C60-ammonium ion 51b.
Figure 34: Triptycene-based macrotricyclic dibenzo-[24]-crown-8 ether host 52 and guests.
Figure 35: Copper imido diacetic acid azacrown receptor 53a and the suggested His-Lys binding motif; a copper ...
Figure 36: Urea (54) and thiourea (55) benzo crown receptor for transport and extraction of amino acids.
Figure 37: Crown pyryliums ion receptors 56 for amino acids.
Figure 38: Ditopic sulfonamide bridged crown ether receptor 57.
Figure 39: Luminescent peptide receptor 58.
Figure 40: Luminescent receptor 59 for the detection of D-glucosamine hydrochloride in water/ethanol and lumin...
Figure 41: Guanidinium azacrown receptor 61 for simple amino acids and ditopic receptor 62 with crown ether an...
Figure 42: Chiral bicyclic guanidinium azacrown receptor 63 and similar receptor 64 for the enantioselective t...
Figure 43: Receptors for zwitterionic species based on luminescent CEAAs.
Figure 44: 1,10-Azacrown ethers with sugar podand arms and the anticancer agent busulfan.
Figure 45: Benzo-18-crown-6 modified β-cyclodextrin 69 and β-cyclodextrin functionalized with diaza-18-crown-6...
Figure 46: Receptors for colorimetric detection of primary and secondary ammonium ions.
Figure 47: Porphyrine-crown-receptors 72.
Figure 48: Porphyrin-crown ether conjugate 73 and fullerene-ammonium ion guest 74.
Figure 49: Calix[4]arene (75a), homooxocalix[4]arene (75b) and resorcin[4]arene (75c) compared (R = H, alkyl c...
Figure 50: Calix[4]arene and ammonium ion guest (R = H, alkyl, OAcyl etc.), possible binding sites; A: co-ordi...
Figure 51: Typical guests for studies with calixarenes and related molecules.
Figure 52: Lower rim modified p-tert-butylcalix[5]arenes 82.
Figure 53: The first example of a water soluble calixarene.
Figure 54: Sulfonated water soluble calix[n]arenes that bind ammonium ions.
Figure 55: Displacement assay for acetylcholine (3) with a sulfonato-calix[6]arene (84b).
Figure 56: Amino acid inclusion in p-sulfonatocalix[4]arene (84a).
Figure 57: Calixarene receptor family 86 with upper and lower rim functionalization.
Figure 58: Calix[6]arenes 87 with one carboxylic acid functionality.
Figure 59: Sulfonated calix[n]arenes with mono-substitution at the lower rim systematically studied on their r...
Figure 60: Cyclotetrachromotropylene host (91) and its binding to lysine (81c).
Figure 61: Calixarenes 92 and 93 with phosphonic acids groups.
Figure 62: Calix[4]arene tetraphosphonic acid (94a) and a double bridged analogue (94b).
Figure 63: Calix[4]arene tetraphosphonic acid ester (92c) for surface recognition experiments.
Figure 64: Calixarene receptors 95 with α-aminophosphonate groups.
Figure 65: A bridged homocalix[3]arene 95 and a distally bridged homocalix[4]crown 96.
Figure 66: Homocalix[3]arene ammonium ion receptor 97a and the Reichardt’s dye (97b) for colorimetric assays.
Figure 67: Chromogenic diazo-bridged calix[4]arene 98.
Figure 68: Calixarene receptor 99 by Huang et al.
Figure 69: Calixarenes 100 reported by Parisi et al.
Figure 70: Guest molecules for inclusion in calixarenes 100: DAP × 2 HCl (101a), APA (101b) and Lys-OMe × 2 HC...
Figure 71: Different N-linked peptido-calixarenes open and with glycol chain bridges.
Figure 72: (S)-1,1′-Bi-2-naphthol calixarene derivative 104 published by Kubo et al.
Figure 73: A chiral ammonium-ion receptor 105 based on the calix[4]arene skeleton.
Figure 74: R-/S-phenylalaninol functionalized calix[6]arenes 106a and 106b.
Figure 75: Capped homocalix[3]arene ammonium ion receptor 107.
Figure 76: Two C3 symmetric capped calix[6]arenes 108 and 109.
Figure 77: Phosphorous-containing rigidified calix[6]arene 110.
Figure 78: Calix[6]azacryptand 111.
Figure 79: Further substituted calix[6]azacryptands 112.
Figure 80: Resorcin[4]arene (75c) and the cavitands (113).
Figure 81: Tetrasulfonatomethylcalix[4]resorcinarene (114).
Figure 82: Resorcin[4]arenes (115a/b) and pyrogallo[4]arenes (115c, 116).
Figure 83: Displacement assay for acetylcholine (3) with tetracyanoresorcin[4]arene (117).
Figure 84: Tetramethoxy resorcinarene mono-crown-5 (118).
Figure 85: Components of a resorcinarene based displacement assay for ammonium ions.
Figure 86: Chiral basket resorcin[4]arenas 121.
Figure 87: Resorcinarenes with deeper cavitand structure (122).
Figure 88: Resorcinarene with partially open deeper cavitand structure (123).
Figure 89: Water-stabilized deep cavitands with partially structure (124, 125).
Figure 90: Charged cavitands 126 for tetralkylammonium ions.
Figure 91: Ditopic calix[4]arene receptor 127 capped with glycol chains.
Figure 92: A calix[5]arene dimer for diammonium salt recognition.
Figure 93: Calixarene parts 92c and 129 for the formation molecular capsules.
Figure 94: Encapsulation of a quaternary ammonium cation by two resorcin[4]arene molecules (NMe4+@[75c]2 × Cl−...
Figure 95: Encapsulation of a quaternary ammonium cation by six resorcin[4]arene molecules (NMe3D+@[130]6 × Cl−...
Figure 96: Structure and schematic of cucurbit[6]uril (CB[6], 131a).
Figure 97: Cyclohexanocucurbit[6]uril (CB′[6], 132) and the guest molecule spermine (133).
Figure 98: α,α,δ,δ-Tetramethylcucurbit[6]uril (134).
Figure 99: Structure of the cucurbituril-phthalhydrazide analogue 135.
Figure 100: Organic cavities for the displacement assay for amine differentiation.
Figure 101: Displacement assay methodology for diammonium- and related guests involving cucurbiturils and some ...
Figure 102: Nor-seco-Cucurbituril (±)-bis-ns-CB[6] (140) and guest molecules.
Figure 103: The cucurbit[6]uril based complexes 141 for chiral discrimination.
Figure 104: Cucurbit[7]uril (131c) and its ferrocene guests (142) opposed.
Figure 105: Cucurbit[7]uril (131c) guest inclusion and representative guests.
Figure 106: Cucurbit[7]uril (131c) binding to succinylcholine (145) and different bis-ammonium and bis-phosphon...
Figure 107: Paraquat-cucurbit[8]uril complex 149.
Figure 108: Gluconuril-based ammonium receptors 150.
Figure 109: Examples of clefts (151a), tweezers (151b, 151c, 151d) and clips (151e).
Figure 110: Kemp’s triacid (152a), on example of Rebek’s receptors (152b) and guests.
Figure 111: Amino acid receptor (154) by Rebek et al.
Figure 112: Hexagonal lattice designed hosts by Bell et al.
Figure 113: Bell’s amidinium receptor (156) and the amidinium ion (157).
Figure 114: Aromatic phosphonic acids.
Figure 115: Xylene phosphonates 159 and 160a/b for recognition of amines and amino alcohols.
Figure 116: Bisphosphonate recognition motif 161 for a colorimetric assay with alizarin complexone (163) for ca...
Figure 117: Bisphosphonate/phosphate clip 164 and bisphosphonate cleft 165.
Figure 118: N-Methylpyrazine 166a, N-methylnicotinamide iodide (166b) and NAD+ (166c).
Figure 119: Bisphosphate cavitands.
Figure 120: Bisphosphonate 167 of Schrader and Finocchiaro.
Figure 121: Tweezer 168 for noradrenaline (80b).
Figure 122: Different tripods and heparin (170).
Figure 123: Squaramide based receptors 172.
Figure 124: Cage like NH4+ receptor 173 of Kim et al.
Figure 125: Ammonium receptors 174 of Chin et al.
Figure 126: 2-Oxazolin-based ammonium receptors 175a–d and 176 by Ahn et al.
Figure 127: Racemic guest molecules 177.
Figure 128: Tripods based on a imidazole containing macrocycle (178) and the guest molecules employed in the st...
Figure 129: Ammonium ion receptor 180.
Figure 130: Tetraoxa[3.3.3.3]paracyclophanes 181 and a cyclophanic tetraester (182).
Figure 131: Peptidic bridged paraquat-cyclophane.
Figure 132: Shape-selective noradrenaline host.
Figure 133: Receptor 185 for binding of noradrenaline on surface layers from Schrader et al.
Figure 134: Tetraphosphonate receptor for binding of noradrenaline.
Figure 135: Tetraphosphonate 187 of Schrader and Finocchiaro.
Figure 136: Zinc-Porphyrin ammonium-ion receptors 188 and 189 of Mizutani et al.
Figure 137: Zinc porphyrin receptor 190.
Figure 138: Zinc porphyrin receptors 191 capable of amino acid binding.
Figure 139: Zinc-porphyrins with amino acid side chains for stereoinduction.
Figure 140: Bis-zinc-bis-porphyrin based on Tröger’s base 193.
Figure 141: BINAP-zinc-prophyrin derivative 194 and it’s guests.
Figure 142: Bisaryl-linked-zinc-porphyrin receptors.
Figure 143: Bis-zinc-porphyrin 199 for diamine recognition and guests.
Figure 144: Bis-zinc-porphyrin crown ether 201.
Figure 145: Bis-zinc-porphyrin 202 for stereodiscrimination (L = large substituent; S = small substituent).
Figure 146: Bis-zinc-porphyrin[3]rotaxane and its copper complex and guests.
Figure 147: Dien-bipyridyl ligand 206 for co-ordination of two metal atoms.
Figure 148: The ligand and corresponding tetradentate co-complex 207 serving as enantioselective receptor for a...
Figure 149: Bis(oxazoline)–copper(II) complex 208 for the recognition of amino acids in aqueous solution.
Figure 150: Zinc-salen-complexes 209 for the recognition tertiary amines.
Figure 151: Bis(oxazoline)–copper(II) 211 for the recognition of amino acids in aqueous solution.
Figure 152: Zn(II)-complex of a C2 terpyridine crown ether.
Figure 153: Displacement assay and receptor for aspartate over glutamate.
Figure 154: Chiral complex 214 for a colorimetric displacement assay for amino acids.
Figure 155: Metal complex receptor 215 with tripeptide side arms.
Figure 156: A sandwich complex 216 and its displaceable dye 217.
Figure 157: Lanthanide complexes 218–220 for amino acid recognition.
Figure 158: Nonactin (221), valinomycin (222) and vancomycin (223).
Figure 159: Monesin (224a) and a chiral analogue for enantiodiscrimination of ammonium guests (224b).
Figure 160: Chiral podands (226) compared to pentaglyme-dimethylether (225) and 18-crown-6 (4).
Figure 161: Lasalocid A (228).
Figure 162: Lasalocid derivatives (230) of Sessler et al.
Figure 163: The Coporphyrin I tetraanion (231).
Figure 164: Linear and cyclic peptides for ammonium ion recognition.
Figure 165: Cyclic and bicyclic depsipeptides for ammonium ion recognition.
Figure 166: α-Cyclodextrin (136a) and novocaine (236).
Figure 167: Helical diol receptor 237 by Reetz and Sostmann.
Figure 168: Ammonium binding spherand by Cram et al. (238a) and the cyclic[6]metaphenylacetylene 238b in compar...
Figure 169: Receptor for peptide backbone and ammonium binding (239).
Figure 170: Anion sensor principle with 3-hydroxy-2-naphthanilide of Jiang et al.
Figure 171: 7-bromo-3-hydroxy-N-(2-hydroxyphenyl)naphthalene 2-carboxamide (241) and its amine binding.
Figure 172: Naturally occurring catechins with affinity to quaternary ammonium ions.
Figure 173: Spiropyran (244) and merocyanine form (244a) of the amino acid receptors of Fuji et al.
Figure 174: Coumarin aldehyde (245) and its iminium species with amino acid bound (245a) by Glass et al.
Figure 175: Coumarin aldehyde appended with boronic acid.
Figure 176: Quinolone aldehyde dimers by Glass et al.
Figure 177: Chromogenic ammonium ion receptors with trifluoroacetophenone recognition motifs.
Figure 178: Chromogenic ammonium ion receptor with trifluoroacetophenone recognition motif bound on different m...
