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Search for "resorcin[4]arene" in Full Text gives 10 result(s) in Beilstein Journal of Organic Chemistry.
Switchable molecular tweezers: design and applications
- Pablo Msellem,
- Maksym Dekthiarenko,
- Nihal Hadj Seyd and
- Guillaume Vives
Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45
Graphical Abstract
Figure 1: Principle of switchable molecular tweezers.
Figure 2: Principle of pH-switchable molecular tweezers 1 [19].
Figure 3: a) pH-Switchable tweezers 2 substituted with alkyl chains as switchable lipids. b) Schematic depict...
Figure 4: Modification of spectral properties of 3 by controlled induction of Pt–Pt interactions.
Figure 5: Conformational switching of di(hydroxyphenyl)pyrimidine-based tweezer 4 upon alkylation or fluoride...
Figure 6: Hydrazone-based pH-responsive tweezers 5 for mesogenic modulation.
Figure 7: pH-Switchable molecular tweezers 6 bearing acridinium moieties.
Figure 8: a) Terpyridine and pyridine-hydrazone-pyridine analogs molecular tweezers and b) extended pyridine ...
Figure 9: Terpyridine-based molecular tweezers with M–salphen arms and their field of application. Figure 9 was adapt...
Figure 10: a) Terpyridine-based molecular tweezers for diphosphate recognition [48]; b) bishelicene chiroptical te...
Figure 11: Terpyridine-based molecular tweezers with allosteric cooperative binding.
Figure 12: Terpyridine-based molecular tweezers presenting closed by default conformation.
Figure 13: Pyridine-pyrimidine-pyridine-based molecular tweezers.
Figure 14: Coordination-responsive molecular tweezers based on nitrogen-containing ligands.
Figure 15: Molecular tweezers exploiting the remote bipyridine or pyridine binding to trigger the conformation...
Figure 16: Bipyridine-based molecular tweezers exploiting the direct s-trans to s-cis-switching for a) anion b...
Figure 17: a) Podand-based molecular tweezers [66,67]. b) Application of tweezers 32 for the catalytic allosteric reg...
Figure 18: Anion-triggered molecular tweezers based on calix[4]pyrrole.
Figure 19: Anion-triggered molecular tweezers.
Figure 20: a) Principle of the weak link approach (WLA) developed by Mirkin and its application to b) symmetri...
Figure 21: Molecular tweezers as allosteric catalyst in asymmetric epoxide opening [80].
Figure 22: Allosteric regulation of catalytic activity in ring-opening polymerization with double tweezers 41.
Figure 23: a) Conformational switching of 42 by intramolecular –S–S– bridge formation. b) Shift of conformatio...
Figure 24: a) Redox-active glycoluril-TTF tweezers 44. b) Mechanism of stepwise oxidation of said tweezers wit...
Figure 25: Mechanism of formation of the mixed-valence dimers of tweezers 45.
Figure 26: Mechanism of carbohydrate liberation upon redox-mediated conformation switching of 46.
Figure 27: a) The encapsulation properties of 47 as well as the DCTNF release process from its host–guest comp...
Figure 28: Redox-active bipyridinium-based tweezers. a) With a ferrocenyl hinge 49, b) with a propyl hinge 50 ...
Figure 29: Redox-active calix[4]arene porphyrin molecular tweezers.
Figure 30: a) Mechanism of the three orthogonal stimuli. b) Cubic scheme showing the eight different states of ...
Figure 31: Redox-controlled molecular gripper based on a diquinone resorcin[4]arene.
Figure 32: a) Shinkai's butterfly tweezers and their different host–guest properties depending on the isomer. ...
Figure 33: Cyclam-tethered tweezers and their different host–guest complexes depending on their configuration.
Figure 34: Azobenzene-based catalytic tweezers.
Figure 35: Photoswitchable PIEZO channel mimic.
Figure 36: Stilbene-based porphyrin tweezers for fullerene recognition.
Figure 37: Stiff-stilbene-based tweezers with urea or thiourea functional units for a) anion binding, b) anion...
Figure 38: Feringa’s photoswitchable organocatalyst (a) and different catalyzed reactions with that system (b)....
Figure 39: a) Irie and Takeshita’s thioindigo-based molecular tweezers. b) Family of hemithioindigo-based mole...
Figure 40: Dithienylethylene crown ether-bearing molecular tweezers reported by Irie and co-workers.
Complexes of resorcin[4]arene with secondary amines: synthesis, solvent influence on “in-out” structure, and theoretical calculations of non-covalent interactions
- Waldemar Iwanek
Beilstein J. Org. Chem. 2023, 19, 1525–1536, doi:10.3762/bjoc.19.109
- exchange and dispersion interactions in CHCl3 in relation to DMSO are the driving forces behind the placement of sec-amine molecules into the R[4]A cavity and the formation of “in” type complexes. Keywords: complexes; DFT calculations; hydrogen bond; resorcin[4]arene; supramolecular chemistry
Graphical Abstract
Scheme 1: Scheme of the formation of R[4]A complexes with sec-amines in ethanol depending on the amine used.
Figure 1: 1H NMR spectra of the 1:1 complex of R[4]A with pyrrolidine in DMSO-d6 and CDCl3 solution. The inte...
Scheme 2: The procedure for finding the most energetically stable complex R[4]A with a sec-amine and calculat...
Figure 2: Theoretically calculated (PBE0-D4/def2-mTZVPP/CPCM) structures of the R[4]A:pyrrolidine complex in ...
Figure 3: Structures of complexes with 1:1 stoichiometry between R[4]A and sec-amines in CHCl3 and DMSO, calc...
Figure 4: Geometrically optimized (PBE0-D4/def2-mTZVPP/CPCM(DMSO) structures of complexes with 1:2 stoichiome...
Figure 5: pKa values of protons of hydroxy groups not involved in the formation of hydrogen bonds in the R[4]...
A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions
- Tommaso Lorenzetto,
- Fabrizio Fabris and
- Alessandro Scarso
Beilstein J. Org. Chem. 2022, 18, 337–349, doi:10.3762/bjoc.18.38
- Tommaso Lorenzetto Fabrizio Fabris Alessandro Scarso Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari di Venezia, via Torino 155, 30172, Mestre-Venezia, Italy 10.3762/bjoc.18.38 Abstract The hexameric resorcin[4]arene capsule as a self-assembled organocatalyst promotes a
- compared to many other strong Brønsted or Lewis acids. Keywords: cationic intermediates; encapsulation; organocatalysis; resorcin[4]arene hexamer; supramolecular catalysis; Introduction In enzymatic catalysis, the substrate is selected matching the size, shape and specific functional groups present in
- [20] or hydrogen bonding units. In the latter case, a key role is played by the resorcin[4]arene 1 as a one-step multigram synthesis product, that spontaneously self-assembles in wet apolar solvents like chloroform or benzene forming a hexameric structure [21] thanks to the formation of a seam of
Graphical Abstract
Scheme 1: Resorcin[4]arene 1 forming the corresponding hexameric capsule 16 and the species used for control ...
Scheme 2: Carbonyl–ene intramolecular cyclization of (S)-citronellal to the corresponding diastereoisomeric c...
Figure 1: 1H NMR spectra in water-saturated CDCl3 except for G. A: [16] (7.5 mM); B: citronellal; C: citronel...
Scheme 3: Dehydration reaction of 1,1-diphenylethanol to 1,1-diphenylethylene.
Figure 2: 1H NMR spectra in water-saturated CDCl3 except for G. A: [16] (7.5 mM); B: 1,1-diphenylethanol; C: ...
Scheme 4: Possible isomerization products from β-pinene and α-pinene.
Figure 3: 1H NMR spectra in water-saturated CDCl3 except for G. A: [16] (7.5 mM); B: α-pinene; C: α-pinene (7...
Figure 4: 1H NMR spectra in water-saturated CDCl3 except for G. A: [16] (7.5 mM); B: β-pinene; C: β-pinene (7...
Figure 5: 1H NMR spectra in water-saturated CDCl3, except for E. A: [16] (7.5 mM); B: β-pinene; C: β-pinene (...
Diametric calix[6]arene-based phosphine gold(I) cavitands
- Gabriele Giovanardi,
- Andrea Secchi,
- Arturo Arduini and
- Gianpiero Cera
Beilstein J. Org. Chem. 2022, 18, 190–196, doi:10.3762/bjoc.18.21
- , calix[4]- [9][10][11][12][13] and resorcin[4]arene [14][15][16][17] are the most exploited cavitands due to their inherent limited flexibility and already proved their ability to control the catalytic activity of late-transition metals and particularly gold(I) catalysts [18][19][20][21][22][23][24][25
- 7.48–7.20 (m, 5H), 6.93 (d, J = 16.2 Hz, 1H), 6.48 (d, J = 16.2 Hz, 1H), 5.73 (ddd, J = 2.7, 1.9, 0.9 Hz, 1H), 4.23–4.14 (m, 4H), 3.28 (dd, J = 1.9, 0.9 Hz, 2H), 3.18 (dd, J = 1.9, 0.9 Hz, 2H), 1.32–1.21 (m, 6H). Selected examples of: a) calix[4]arene-; b) resorcin[4]arene-; c) calix[6]arene-gold(I
Graphical Abstract
Figure 1: Selected examples of: a) calix[4]arene-; b) resorcin[4]arene-; c) calix[6]arene-gold(I) macrocyclic...
Scheme 1: i) NH2NH2∙H2O, Pd/C in EtOH, 80 °C (quant.); ii) diphenylphosphinobenzoic acid, EDC∙HCl, DMAP (cat....
Figure 2: Stacked-plot, mid-field expanded region of the 1H NMR spectrum (400 MHz, 298 K) of A(AuCl)2, B(AuCl)...
Figure 3: Stacked plot 1H NMR (tetrachloroethane-d2) of A(AuCl)2 at variable temperature.
Scheme 2: Synthesis of the monomeric gold catalyst analogues A’,B’,C’(AuCl). Conditions: i) diphenylphosphino...
Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers
- Anniina Kiesilä,
- Jani O. Moilanen,
- Anneli Kruve,
- Christoph A. Schalley,
- Perdita Barran and
- Elina Kalenius
Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241
- dimeric resorcin[4]arene and pyridine[4]arene capsules, we highlight here unique host–guest properties of pyridinearene capsules. In marked contrast to the corresponding resorcin[4]arene capsules, cation binding is clearly feasible, when anions bind in an exo-site and support cation encapsulation by
- towards the Me4N+ cation was compared to that of resorcin[4]arene, which is known to bind small cations with high affinity. 1, 2 and Me4NPF6 were mixed in 1:1:1 ratio and measured by ESI-QTOF-MS. As seen in Figure 2, the resorcin[4]arene dimer [22 + Me4N]+ was detected as the base peak in the positive
- complexation of solvent was also only detected with the pyridinearene homodimer (for example as the [12 + MeCN + PF6]− ion). This mixed host experiment shows the resorcin[4]arene affinity towards Me4N+ to be higher than that of pyridine[4]arene. Also, the lack of anion and/or solvent complex formation with 2
Graphical Abstract
Scheme 1: Structures of tetraisobutylpyridine[4]arene 1 and tetraisobutylresorcin[4]arene 2.
Figure 1: Spectra of 1 + Me4NPF6 1:3 in acetone in a) (+)ESI-MS and b) (−)ESI-MS. Insets showing arrival time...
Figure 2: (+)ESI-MS profile spectrum of the mixture of 1, 2 and TMAPF6 in acetonitrile (20 µM, 1:1:1). Inset ...
Figure 3: Calculated ESP surfaces (in au) superimposed on the total electron density (0.004 au) for 1 and 2: ...
Fluorinated azobenzenes as supramolecular halogen-bonding building blocks
- Esther Nieland,
- Oliver Weingart and
- Bernd M. Schmidt
Beilstein J. Org. Chem. 2019, 15, 2013–2019, doi:10.3762/bjoc.15.197
- in the field of crystal engineering [1]. Only few supramolecular capsules were reported so far [29], including the resorcin[4]arene capsules of Diederich and co-workers [21][23], triangular macrocycles assembled by self-complemented halogen bonding [20] and halogen bond templated, polyfluorinated
Graphical Abstract
Scheme 1: a) Azobenzenes A1–3 employed in this study. b) U-shaped anthracene halogen bond acceptor bearing tw...
Figure 1: Electrostatic potential map at different isodensity values (B3LYP/ def2/TZVP/DGZVP optimized geomet...
Figure 2: Top: Vertical electronic absorption spectra of a) A2 and b) A3, calculated using TD-B3LYP/def2-TZVP...
Figure 3: a) Space-filling model of U1···A2. The kinked alignment of both the lutidine units of U1 and the az...
Complexation of chiral amines by resorcin[4]arene sulfonic acids in polar media – circular dichroism and diffusion studies of chirality transfer and solvent dependence
- Bartosz Setner and
- Agnieszka Szumna
Beilstein J. Org. Chem. 2019, 15, 1913–1924, doi:10.3762/bjoc.15.187
- chemistry. In the present study we demonstrate that resorcin[4]arene sulfonic acid (RSA) interacts with chiral amines (amino acid derivatives and aminocavitands) to form inclusion complexes and capsules based on electrostatic interactions. The complexes were characterized by circular dichroism and DOSY NMR
- disintegrative for these complexes. This result is quite non-intuitive and worth attention in the context of formation of supramolecular complexes in polar environment, for which DMSO is most often a first-choice solvent. Keywords: cavitands; chirality; macrocycle; resorcin[4]arene; self-assembly
- cyclodextrines, which, when unmodified, interact with a wide range of hydrophobic guests albeit with low general selectivity and enantioselectivity in particular [6]. In this paper we present a group of synthetic macrocyclic compounds – resorcin[4]arene sulfonic acids (RSAs) and analyze their interactions with
Graphical Abstract
Figure 1: Structures of the compounds used in this study and labelling scheme for NMR spectra.
Figure 2: Spectra of complexes [1(LysOMe)2], [1(ArgOMe)2], [1(HisOMe)2]: 1H NMR (a–g) and ROESY (h–j) in meth...
Figure 3: CD (a) and UV (b) spectra of complexes [1(LysOMe)2], [1(PheOMe)2], [1(ValOMe)2], [1(ArgOMe)2], and [...
Figure 4: DOSY spectra of 1 (a), [1(LysOMe)2] (b), [1(ArgOMe)2] (c), [1(HisOMe)2] (d) and [LysOMe + 1(LysOMe)2...
Figure 5: 1H NMR spectra of 1 (a), LysOMe (b), 1H NMR and DOSY spectra of [1(LysOMe)2] (insets show the shape...
Figure 6: 1H NMR spectra of (R)-2 (a); [1((R)-2] (b); [1 + 1((R)-2] (c) (insets show the shape of signals f, ...
Figure 7: 1H NMR and DOSY spectra of (R)-2 (a); [1(R)-2] (b) (inset show the shape signals f, DMSO-d6, 298K, ...
Enantioselective supramolecular devices in the gas phase. Resorcin[4]arene as a model system
- Caterina Fraschetti,
- Matthias C. Letzel,
- Antonello Filippi,
- Maurizio Speranza and
- Jochen Mattay
Beilstein J. Org. Chem. 2012, 8, 539–550, doi:10.3762/bjoc.8.62
- counterion effects. Keywords: diastereomeric complexes; gas phase enantioselectivity; kinetics; mass spectrometry; resorcin[4]arene receptor; Review Enzymes are macromolecular assemblies that make up the machinery whose structures and dynamics enable and support life functions. They are invariably
- , strongly dependent on the isomeric structure of the used guest [10]. Resorcin[4]arene molecules are characterized by three main contact regions [11]: (1) The down-region is the cavity of the receptor, which can be hydrophilic or lipophilic depending on the nature of the lateral chains; (2) The external
- the attention will be focussed on the most recent results obtained by our group with this particular kinetic method. Methodology The proton-bound [M∙H∙G]+ aggregates (M: chiral hosting resorcin[4]arene; G: guest biomolecule) were generated by electrospray ionization (ESI) of M/G methanolic mixtures
Graphical Abstract
Figure 1: Examples of monoexponential decay: The slope of the line directly provides the reaction pseudo-firs...
Figure 2: Example of biexponential decay.
Figure 3: Amidoresorcin[4]arene YS.
Scheme 1: Studied (a) peptidoresorcin[4]arenes and (b) dipeptidic guests.
Figure 4: Catharanthine and vindoline, monomers constituting the anticancer vinblastine and the analogous vin...
Figure 5: Stable conformers of catharanthine.
Figure 6: Global minima of (a) [VS∙H∙T]+ and (b) [VR∙H∙T]+ complexes.
Figure 7: Guests studied in [47].
Figure 8: Selected nucleosides.
Figure 9: Example of molecular logic gate.
Figure 10: Cyclochiral resorcin[4]arenes.
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...
Size selective recognition of small esters by a negative allosteric hemicarcerand
- Holger Staats and
- Arne Lützen
Beilstein J. Org. Chem. 2010, 6, No. 10, doi:10.3762/bjoc.6.10
- resorcinarene moieties in different directions so that they cannot act cooperatively in the binding of the substrate. Keywords: allosteric receptors; 2,2′-bipyridine; hemicarcerand; molecular recognition; resorcin[4]arene; Introduction Nature uses allosteric effects in a very elegant manner to control
- derivatives of this first example of an allosteric hemicarcerand and their metal complexes formed upon coordination to metal salts or complexes like AgBF4, CuBF4, [Cuphen]BF4, or [(CO)5ReCl] [28]. Among these, bis(resorcin[4]arene) substituted 2,2′-bipyridine 2 is a structural isomer of 1 differing only in
Graphical Abstract
Scheme 1: Bis(resorcinarene) esters of 4,4′- and 4,6′-(2,2′-bipyridyl)dicarboxylic acid, 1 and 2, respectivel...
Scheme 2: Simple esters used as model substrates in this study.
Figure 1: Qualitative binding studies of 2 and the model substrates 3–7. 1H NMR spectra (500.1 MHz, 298 K in ...
Figure 2: 1H NMR titration (500.1 MHz, 298 K, c0(2) = 5.3 mmol/L) of 2 with increasing amounts of ethyl aceta...
Scheme 3: Binding model of the negative cooperative allosteric behaviour of 2.
