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Search for "cucurbituril" in Full Text gives 14 result(s) in Beilstein Journal of Organic Chemistry.
Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups
- Christian Akakpo,
- Peter Y. Zavalij and
- Lyle Isaacs
Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55
- specific guest. C1 binds more tightly to quaternary ammonium guests compared to the corresponding primary ammonium ions. Keywords: cucurbituril; host–guest chemistry; isothermal titration calorimetry; molecular container; X-ray crystallography; Introduction Molecular recognition interactions are key
Graphical Abstract
Figure 1: Chemical structures of CB[n] and selected acyclic CB[n]-type molecular containers M1 and M0.
Scheme 1: Synthesis of C1. Conditions: a) TFA/Ac2O, 70 °C, 3.5 h, 71%; b) LiOH, 50 °C, 69%; c) dry pyridine, ...
Figure 2: a) 1H NMR spectrum (600, D2O, rt) and b) 13C NMR spectrum recorded (150 MHz, D2O, rt) for C1.
Figure 3: Chemical structures of guests used in this study along with the complexation induced changes in che...
Figure 4: 1H NMR spectra recorded (400 MHz, D2O, rt) for: a) Me6PXDA (0.5 mM), b) a mixture of C1 (0.5 mM) an...
Figure 5: Cross-eyed stereoview of the C1·Me6CHDA complex in the crystal. Color code: C, gray; H, white; N, b...
Figure 6: Cross-eyed stereoview of the crystal packing observed in the molecular cell of C1·Me6CHDA. H-atoms ...
Figure 7: a) Representative plot of DP (μcal s−1) versus time from the titration of C1 (0.1 mM) in the ITC ce...
Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization
- Wentao Yu,
- Zhiyao Yang,
- Chengkan Yu,
- Xiaowei Li and
- Lihua Yuan
Beilstein J. Org. Chem. 2025, 21, 179–188, doi:10.3762/bjoc.21.10
- cucurbituril [18], cyclodextrin [19], and calix[4]pyrrole [20], as well as flexible crown ethers [10][21]. Few two-dimensional (2D) shape-persistent macrocyclic compounds are used for this purpose. One difficulty in realizing 2D macrocycle-based orthogonal assembly is that the construction motif must be
Graphical Abstract
Scheme 1: a) Chemical structures of H-bonded macrocycles H1, H2, and guest G1, and schematic representation o...
Figure 1: ESIMS spectrum of an equimolar mixture of G1 and H1 in CHCl3/CH3CN (1:1, v/v), including calculated...
Figure 2: Stacked 1H NMR spectra (CDCl3/CD3CN 1:1, v/v, 400 MHz, 298 K) of G1 upon addition of different equi...
Figure 3: Single-crystal X-ray structure of the complex H2 ⊃ G1. a) Dimeric structure formed by cyclo[6]arami...
Figure 4: Stacked 1H NMR spectra (CDCl3/CD3CN 1:1, v/v, 400 MHz, 298 K) of G2 upon addition of different equi...
Figure 5: TEM images of a solution of H1, G2, and Zn(ClO4)2 at different concentrations (CHCl3/CH3CN 1:1, v/v...
Figure 6: Stacked 1H NMR spectra (CDCl3/CD3CN 1:1, v/v, 400 MHz, 298 K) of G2 and Zn2+ upon addition of diffe...
Figure 7: Specific viscosity of the linear supramolecular polymer in CHCl3/CH3CN (1:1, v/v, 298 K) at variabl...
Figure 8: Variable-concentration 1H NMR spectra of the supramolecular polymer: (a) 2.0 mM, (b) 4.0 mM, (c) 6....
Light-responsive rotaxane-based materials: inducing motion in the solid state
- Adrian Saura-Sanmartin
Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64
- cyclobutanes (Figure 4b). Interestingly, the changes in the crystalline array as a consequence of this photodimerization within the cucurbituril macrocycles also induced a macroscopic deformation of the metal-organic material, promoting a photomechanical bending of the crystals. This photomechanical
Graphical Abstract
Figure 1: a) Chemical structure of pseudorotaxanes 1; and (b) single-crystal X-ray structure of rotaxane 1a (R...
Figure 2: (a) Chemical structure of polyrotaxane 2; and (b) cartoon representation of the light-triggered deg...
Figure 3: a) Chemical structures of rotaxanes (E)-3 and (Z)-3; b) stick representation of the solid structure...
Figure 4: Stick representations of the solid structures of: (a) U-CB[8]-MPyVB showing an interlocked ligand c...
Study on the interactions between melamine-cored Schiff bases with cucurbit[n]urils of different sizes and its application in detecting silver ions
- Jun-Xian Gou,
- Yang Luo,
- Xi-Nan Yang,
- Wei Zhang,
- Ji-Hong Lu,
- Zhu Tao and
- Xin Xiao
Beilstein J. Org. Chem. 2021, 17, 2950–2958, doi:10.3762/bjoc.17.204
- host–guest interactions. Among them, Q[7]-TBT is selected as a UV detector for the detection of silver ions (Ag+). This work makes full use of the characteristics of each cucurbituril and melamine-cored Schiff base to construct a series of complexes and these are applied to metal detection. Keywords
Graphical Abstract
Scheme 1: The Structures of Q[7], Q[8], TMeQ[6], and TBT.
Figure 1: The 1H NMR titration of TBT (1 mM) with an increasing amount of TMeQ[6] from 0 (i), 0.1 (ii), 0.2 (...
Figure 2: The 1H NMR titration of TBT (1 mM) with an increasing amount of Q[7] from 0 (i), 0.1 (ii), 0.5 (iii...
Figure 3: The UV–vis spectra (a) of TBT (20 μM) with an increasing amount of Q[7] from 0.0 to 4.0 equiv; the ...
Figure 4: The UV–vis spectra (a) of TBT (20 μM) with an increasing amount of Q[8] from 0.0 to 4.0 equiv and t...
Figure 5: The UV–vis spectra (a) of Q[7]-TBT (3:1, 20 μM) affected by Mn+ (50 equivalents); histogram of (b) ...
Figure 6: The UV–vis spectra (a) of Q[7]-TBT (20 μM) with an increasing amount of Ag+ from 0.0 to 2.0 equiv; ...
Scheme 2: The synthesis of TBT.
Synthesis of a novel aminobenzene-containing hemicucurbituril and its fluorescence spectral properties with ions
- Qingkai Zeng,
- Qiumeng Long,
- Jihong Lu,
- Li Wang,
- Yuting You,
- Xiaoting Yuan,
- Qianjun Zhang,
- Qingmei Ge,
- Hang Cong and
- Mao Liu
Beilstein J. Org. Chem. 2021, 17, 2840–2847, doi:10.3762/bjoc.17.195
- . Hemicucurbit[n]urils (HQ[n]) and relevant derivatives [24] represent as a sub-group of the cucurbituril family [25], possessing much more flexible structures than Q[n]s, and are generally characterized by an electroneutral cavity and a negative electro-potential portal. Comparing the coordination properties of
Graphical Abstract
Scheme 1: The evolution of hemicucurbituril analogs.
Scheme 2: The route for the synthesis of aminobenzene-containing hemicucurbituril 4.
Figure 1: The X-ray structure of nitrobenzene-containing hemicucurbituril 9 (CCDC 2094879).
Figure 2: Fluorescence emission spectra (λmax = 349 nm) of 4 (2.5 × 10−5 M) in the presence of 10 equivalents...
Figure 3: Column diagram of fluorescence quenching efficiency of 4 (2.5 × 10−5 M) in the presence of 10 equiv...
Figure 4: Fluorescence emission spectra (λmax = 349 nm) of 4 (2.5 × 10−5 M) in the presence of Fe3+ and Cu2+ ...
Figure 5: Fluorescence emission spectra (λmax = 349 nm) of 4 (2.5 × 10−5 M) in the presence of 20 equivalents...
Figure 6: Column diagram of fluorescence enhancement efficiency of 4 (2.5 × 10−5 M) in the presence of 20 equ...
Insight into functionalized-macrocycles-guided supramolecular photocatalysis
- Minzan Zuo,
- Krishnasamy Velmurugan,
- Kaiya Wang,
- Xueqi Tian and
- Xiao-Yu Hu
Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15
- of electron–hole pairs. Consequently, a high activity of TiO2 could be achieved, and the decolorization of methyl orange was realized efficiently. Cucurbituril-based photocatalysis CBs are a type of macrocyclic molecules made of glycoluril linked by methylene bridges. The name is derived from the
- molecules, binary 1:1 or ternary 1:1:1 complexes can be formed. In view of the unique host–guest binding characteristics, cucurbituril is also often used to construct photocatalytic systems [39][40][41]. The large and hydrophobic cavities of the CBs provide a suitable environment for various photochemical
Graphical Abstract
Figure 1: Chemical structures of representative macrocycles.
Figure 2: Ba2+-induced intermolecular [2 + 2]-photocycloaddition of crown ether-functionalized substrates 1 a...
Figure 3: Energy transfer system constructed of a BODIPY–zinc porphyrin–crown ether triad assembly bound to a...
Figure 4: The sensitizer 5 was prepared by a flavin–zinc(II)–cyclen complex for the photooxidation of benzyl ...
Figure 5: Enantiodifferentiating Z–E photoisomerization of cyclooctene sensitized by a chiral sensitizer as t...
Figure 6: Structures of the modified CDs as chiral sensitizing hosts. Adapted with permission from [24], Copyrigh...
Figure 7: Supramolecular 1:1 and 2:2 complexations of AC with the cationic β-CD derivatives 16–21 and subsequ...
Figure 8: Construction of the TiO2–AuNCs@β-CD photocatalyst. Republished with permission of The Royal Society...
Figure 9: Visible-light-driven conversion of benzyl alcohol to H2 and a vicinal diol or to H2 and benzaldehyd...
Figure 10: (a) Structures of CDs, (b) CoPyS, and (c) EY. Republished with permission of The Royal Society of C...
Figure 11: Conversion of CO2 to CO by ReP/HO-TPA–TiO2. Republished with permission of The Royal Society of Che...
Figure 12: Thiacalix[4]arene-protected TiO2 clusters for H2 evolution. Reprinted with permission from [37], Copyri...
Figure 13: 4-Methoxycalix[7]arene film-based TiO2 photocatalytic system. Reprinted from [38], Materials Today Chem...
Figure 14: (a) Photodimerization of 6-methylcoumarin (22). (b) Catalytic cycle for the photodimerization of 22...
Figure 15: Formation of a supramolecular PDI–CB[7] complex and structures of monomers and the chain transfer a...
Figure 16: Ternary self-assembled system for photocatalytic H2 evolution (a) and structure of 27 (b). Figure 16 reprodu...
Figure 17: Structures of COP-1, CMP-1, and their substrate S-1 and S-2.
Figure 18: Supramolecular self-assembly of the light-harvesting system formed by WP5, β-CAR, and Chl-b. Reprod...
Figure 19: Photocyclodimerization of AC based on WP5 and WP6.
NMR Spectroscopy of supramolecular chemistry on protein surfaces
- Peter Bayer,
- Anja Matena and
- Christine Beuck
Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203
- ]arene has been titrated to trimethyl-lysine (KMe3), which yields the largest shifts and most severe line broadening for the methyl protons and Hε resonances, indicating that these atoms are located inside the aromatic bowl of the calixarene [29]. The binding affinities of cucurbituril ligands for
Graphical Abstract
Figure 1: Ligands targeting charged areas on protein surfaces discussed in this review. The protein shown as ...
Figure 2: 1H NMR titration of lysine with tweezers. All signals show chemical shift perturbations and differe...
Figure 3: 1H,15N-HSQC Titration of full-length hPin1 with supramolecular tweezers (original data). (a) Spectr...
Figure 4: Relative signal intensities can be used to identify ligand binding sites (schematic representation ...
Figure 5: Schematic 1H,15N-HSQC spectrum of tauF4 (chemical shifts from BMRB # 17945, [109]) with and without spec...
Figure 6: H2(C)N spectra specific for arginine (a) and lysine (b) residues of the hPin1-WW domain at differen...
Morphology-tunable and pH-responsive supramolecular self-assemblies based on AB2-type host–guest-conjugated amphiphilic molecules for controlled drug delivery
- Yang Bai,
- Cai-ping Liu,
- Di Chen,
- Long-hai Zhuo,
- Huai-tian Bu and
- Wei Tian
Beilstein J. Org. Chem. 2019, 15, 1925–1932, doi:10.3762/bjoc.15.188
- stimuli-responsive supramolecular self-assemblies with regulated self-assembly morphologies due to their response to various external stimuli, such as temperature [12], light [13][14][15], redox [16][17][18], and pH [19][20]. In addition, β-cyclodextrin (β-CD), pillararene and cucurbituril have been
Graphical Abstract
Scheme 1: Schematic illustration of the construction of β-CD-BM2-based supramolecular self-assemblies, their ...
Figure 1: Typical TEM images (a–d) and DLS curves (e) of β-CD-BM2-based supramolecular self-assemblies at pH ...
Figure 2: 1H NMR spectra of β-CD-BM2-based supramolecular self-assemblies in DMSO-d6 (a), D2O (b) and DCl/D2O...
Figure 3: 2D NMR NOESY spectra in D2O (a) and D2O/DCl (b), UV–vis spectra (c) and fluorescence spectra (d) of...
Figure 4: Cumulative release curves of DOX-loaded β-CD-BM2 based SSAs at pH 7.4 and 5.0, respectively.
Figure 5: (a) Cell viability of PC-3 cells after incubated with β-CD-BM2 based FSSAs for 48 h. (b) In vitro c...
Figure 6: CLSM images of PC-3 cells incubated with the FSSAs and free DOX·HCl at a concentration of 5 μg/mL. ...
Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules
- Hendrik V. Schröder and
- Christoph A. Schalley
Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190
- example, the π-electron-rich wheel 8, consisting of two doubly-bridged 1,5-dioxynaphthalenes, is able to form a donor–acceptor complex with the π-electron-poor TTF2+ dication [26]. An astonishing discovery regarding TTF–cucurbituril complexes was made by Kim and co-workers in 2004 (Figure 7) [67]. The
Graphical Abstract
Figure 1: The two one-electron oxidation reactions of tetrathiafulvalene (TTF, 1) and the corresponding prope...
Figure 2: UV–vis spectra and photographs of TTF 2 in its three stable oxidation states (black line = 2, orang...
Figure 3: Structure and conformations of two TTF dimers in solution, the mixed-valence and the radical-cation...
Figure 4: (a) The isomerism problem of TTF. (b)–(d) Major synthetic breakthroughs for the construction of TTF...
Figure 5: (a) Host–guest equilibrium between π-electron-poor cyclophane 3 and different TTFs with their corre...
Figure 6: TTF complexes with different host molecules.
Figure 7: Stable TTF (a) radical-cation and (b) mixed-valence dimers in confined molecular spaces.
Figure 8: A “three-pole supramolecular switch”: Controlled by its oxidation state, TTF (1) jumps back and for...
Figure 9: Redox-controlled closing and opening motion of the artificial molecular lasso 12.
Figure 10: Graphical illustration how a non-degenerate TTF-based shuttle works under electrochemical operation....
Figure 11: The first TTF-based rotaxane 13.
Figure 12: A redox-switchable bistable molecular shuttle 14.
Figure 13: The redox-switchable cyclodextrin-based rotaxane 15.
Figure 14: The redox-switchable non-ionic rotaxane 16 with a pyromellitic diimide macrocycle.
Figure 15: The redox-switchable TTF rotaxane 17 based on a crown/ammonium binding motif.
Figure 16: Structure and operation of the electro- and photochemically switchable rotaxane 18 which acts as po...
Figure 17: (a) The redox-switchable rotaxane 19 with a donor–acceptor pair which is stable in five different s...
Figure 18: Schematic representation of a molecular electronic memory based on a bistable TTF-based rotaxane. (...
Figure 19: Schematic representation of bending motion of a microcantilever beam with gold surface induced by o...
Figure 20: TTF-dimer interactions in a redox-switchable tripodal [4]rotaxane 22.
Figure 21: (a) A molecular friction clutch 23 which can be operated by electrochemical stimuli. (b) Schematic ...
Figure 22: Fusion between rotaxane and catenane: a [3]rotacatenane 24 which can stabilize TTF dimers.
Figure 23: The first TTF-based catenane 25.
Figure 24: Electrochemically controlled circumrotation of the bistable catenane 26.
Figure 25: A tristable switch based on the redox-active [2]catenane 27 with three different stations.
Figure 26: Structure of catenane-functionalized MOF NU-1000 [108] with structural representation of subcomponents. ...
Figure 27: (a) [3]Catenanes 29 and 30 which can stabilize mixed-valence or radical-cation dimers of TTF. (b) S...
Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril
- Mohammad A. Alnajjar,
- Jürgen Bartelmeß,
- Robert Hein,
- Pichandi Ashokkumar,
- Mohamed Nilam,
- Werner M. Nau,
- Knut Rurack and
- Andreas Hennig
Beilstein J. Org. Chem. 2018, 14, 1961–1971, doi:10.3762/bjoc.14.171
- . This includes indicator displacement assays with favourable absorption and emission wavelengths in the visible spectral region, fluorescence correlation spectroscopy, and noncovalent surface functionalization with fluorophores. Keywords: BODIPY; cucurbituril; fluorescence; pH; photoinduced electron
Graphical Abstract
Figure 1: a) The “anchor group” approach for a rational design of CB–dye pairs involving a thermodynamic cycl...
Scheme 1: Synthesis of BODIPY derivatives.
Figure 2: a) Normalized absorption (solid line) and normalized fluorescence emission spectrum (dotted line) o...
Figure 3: a) Fluorescence spectral changes (λexc = 470 nm) upon addition of CB7 to 50 nM 1 in 10 mM citrate b...
Figure 4: Fluorescence pH titration of 2 and the respective complex (in presence of 3 mM CB7) in 30% (v/v) AC...
Figure 5: Fluorescence displacement titrations (λex = 470 nm, λem = 510 nm). a) 5 µM 2 and 2.5 µM CB7 with cy...
Figure 6: FCS autocorrelation curves obtained with 10 nM 2 in the absence (red fitted line) and presence (blu...
Figure 7: Fluorescence microscopy images of 1 mg/mL polymer microspheres a) with or b) without surface-bound ...
Interactions between photoacidic 3-hydroxynaphtho[1,2-b]quinolizinium and cucurbit[7]uril: Influence on acidity in the ground and excited state
- Jonas Becher,
- Daria V. Berdnikova,
- Darinka Dzubiel,
- Heiko Ihmels and
- Phil M. Pithan
Beilstein J. Org. Chem. 2017, 13, 203–212, doi:10.3762/bjoc.13.23
- effect of the ligand–CB[n] interplay may be used to modify and control the photochemical properties of a guest molecule [8][9]. For instance, the encapsulation of photoactive molecules in the constrained medium of a cucurbituril cavity enables the performance of chemo-, regio- or stereoselective
- interactions, whereas the linear phene-type derivatives bind with lesser, but still significant affinity. Considering the size of the cucurbituril host, it may be assumed that the angular molecules experience steric repulsion with the outer-rim carbonyl groups, which does not occur with the linear molecules
- equilibrium to a different extend depending on the ligand structure [54]. Remarkably, the pKa and pKa* values of compound 2 increase by about two to three orders of magnitude, respectively, when bound to CB[7]. Although the change of ground state pKa values of acids on association with cucurbituril hosts is
Graphical Abstract
Figure 1: Structures of quinolizinium derivatives 1a–c and 2.
Scheme 1: Synthesis of 3-hydroxynaphtho[1,2-b]quinolizinium bromide (2).
Figure 2: Absorption (A, c = 100 µM) and normalized emission spectra (B, c = 10 µM or Abs. = 0.1 at λex) of d...
Figure 3: Photometric (A) and fluorimetric (B) acid–base titration (λex = 380 nm) of naphthoquinolizinium 2 (c...
Figure 4: Absorption spectra of 2 (c = 100 µM) in MeOH (A) and MeCN (B). Black lines: without additive, red: ...
Figure 5: Normalized emission spectra of 2 (c = 10 µM) in MeOH (A, λex = 400 nm) and MeCN (B, λex = 398 nm). ...
Figure 6: Photometric titration of CB[7] (c = 0.45 mM) to 2 (c = 15 µM) in BPE buffer (with 10% v/v DMSO) at ...
Figure 7: Photometric (A) and fluorimetric (B) acid–base titration (λex = 380 nm) of 2 (c = 15 µM) in the pre...
Scheme 2: Acid–base equilibrium of hydroxynaphthoquinolizinium 2.
Figure 8: Structures of quinolizinium derivatives 6–8.
Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution
- Hai Ming Wang and
- Gerhard Wenz
Beilstein J. Org. Chem. 2013, 9, 1858–1866, doi:10.3762/bjoc.9.217
- 15 mM aqueous solution of COU proceeded with a low quantum yield Φ = 0.11% and afforded mainly the syn-HH isomer with a reasonable selectivity of syn/anti = 10, as previously described [38][39]. Photodimerization of 6-methyl-COU complexed in cucurbituril CB [8] furnished the syn-HT isomer as the main
Graphical Abstract
Figure 1: Chemical structures of selected aromatic guests: anthracene, ANT; acenaphthylene, ACE; and coumarin...
Figure 2: Structures of γ-CD and γ-CD thioethers 1–7.
Scheme 1: Photodimerization of ACE.
Figure 3: 1H NMR spectrum of the photo product of ACE in the presence of γ-CD thioether 3 in CDCl3.
Figure 4: Schematic drawing of the ACE photodimers in γ-CD: a) the syn photodimer and b) the anti photodimer....
Figure 5: Structures of COU photodimers.
Figure 6: Partial 1H NMR of the photodimers formed after irradiation of COU at various concentrations of Na2SO...
Structures of the reaction products of the AZADO radical with TCNQF4 or thiourea
- Hideto Suzuki,
- Yuta Kawahara,
- Hiroki Akutsu,
- Jun-ichi Yamada and
- Shin’ichi Nakatsuji
Beilstein J. Org. Chem. 2013, 9, 1487–1491, doi:10.3762/bjoc.9.169
- host molecules such as tris(o-phenylenedioxy)cyclotriphosphazene (TPP) [10], cyclodextrin (CD) [11], or cucurbituril (CB) derivatives [12] but the inclusion compound derived from AZADO is still unknown. Here in this paper we wish to report the apparent difference of reactivity between AZADO (2) and
Graphical Abstract
Figure 1: Structural formula of TEMPO (1), AZADO (2), TCNQF4 (3) and thiourea (4).
Scheme 1: Difference of the reaction products from TEMPO (1) and AZADO (2) with TCNQF4 (3).
Figure 2: Molecular structure of the adduct 5 obtained by X-ray analysis.
Scheme 2: A plausible mechanism of the reaction of AZADO (2) with TCNQF4 (3).
Figure 3: UV–vis spectra of 2 (red line), 3 (blue line) and 5 (green line).
Scheme 3: The reaction of 2 with 4 to form 6.
Figure 4: Crystal structure of the inclusion compound 6 obtained by X-ray analysis.
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...
