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Journal articles on the topic 'Cage-amine'

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Published: 4 June 2021

Last updated: 9 February 2022

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1

Long, Augustin, Olivier Perraud, Erwann Jeanneau, Christophe Aronica, Jean-Pierre Dutasta, and Alexandre Martinez. "A hemicryptophane with a triple-stranded helical structure." Beilstein Journal of Organic Chemistry 14 (July 24, 2018): 1885–89. http://dx.doi.org/10.3762/bjoc.14.162.

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A hemicryptophane cage bearing amine and amide functions in its three linkers was synthesized in five steps. The X-ray molecular structure of the cage shows a triple-stranded helical arrangement of the linkers stabilized by intramolecular hydrogen bonds between amide and amine groups. The chirality of the cyclotriveratrylene unit controls the propeller arrangement of the three aromatic rings in the opposite part of the cage. 1H NMR studies suggest that this structure is retained in solution.

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2

Koutsantonis, George A., Gareth L. Nealon, Craig E. Buckley, Mark Paskevicius, Laurent Douce, Jack M. Harrowfield, and Alasdair W. McDowall. "Wormlike Micelles from a Cage Amine Metallosurfactant." Langmuir 23, no. 24 (November 2007): 11986–90. http://dx.doi.org/10.1021/la701283b.

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3

Ma, Michelle T., Margaret S. Cooper, Rowena L. Paul, Karen P. Shaw, John A. Karas, Denis Scanlon, Jonathan M. White, Philip J. Blower, and Paul S. Donnelly. "Macrobicyclic Cage Amine Ligands for Copper Radiopharmaceuticals: A Single Bivalent Cage Amine Containing Two Lys3-bombesin Targeting Peptides." Inorganic Chemistry 50, no. 14 (July 18, 2011): 6701–10. http://dx.doi.org/10.1021/ic200681s.

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4

Modak, Ritwik, Bijnaneswar Mondal, Prodip Howlader, and Partha Sarathi Mukherjee. "Self-assembly of a “cationic-cage” via the formation of Ag–carbene bonds followed by imine condensation." Chemical Communications 55, no. 47 (2019): 6711–14. http://dx.doi.org/10.1039/c9cc02341k.

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We develop a new strategy for the synthesis of a “cationic-cage” (CC-Ag) via metal–carbene (M–C_NHC) bond formation followed by imine condensation. While the aldehyde alone doesn’t yield the desired cage with the amine, Ag–NHC bond formation allows such condensation, leading to the formation of a “cationic-cage”.

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5

Rivera, Augusto, Martı́n E. Núñez, Martha S. Morales-Rı́os, and Pedro Joseph-Nathan. "Preparation of cage amine 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecane." Tetrahedron Letters 45, no. 41 (October 2004): 7563–65. http://dx.doi.org/10.1016/j.tetlet.2004.08.123.

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6

Hong, Dae Ho, Brian J. Knight, Vincent J. Catalano, and Leslie J. Murray. "Isolation of chloride- and hydride-bridged tri-iron and -zinc clusters in a tris(β-oxo-δ-diimine) cyclophane ligand." Dalton Transactions 48, no. 26 (2019): 9570–75. http://dx.doi.org/10.1039/c9dt00799g.

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7

Smith, Paul H., Zelideth E. Reyes, Chi Woo Lee, and Kenneth N. Raymond. "Characterization of a series of lanthanide amine cage complexes." Inorganic Chemistry 27, no. 23 (November 1988): 4154–65. http://dx.doi.org/10.1021/ic00296a015.

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8

Klein, Liv B., Thorbjørn J. Morsing, Ruth A. Livingstone, Dave Townsend, and Theis I. Sølling. "The effects of symmetry and rigidity on non-adiabatic dynamics in tertiary amines: a time-resolved photoelectron velocity-map imaging study of the cage-amine ABCO." Physical Chemistry Chemical Physics 18, no. 14 (2016): 9715–23. http://dx.doi.org/10.1039/c5cp07910a.

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The non-adiabatic relaxation dynamics of the tertiary cage-amine azabicyclo[2.2.2]octane (ABCO) have been investigated following 3p Rydberg excitation at 201 nm using femtosecond time-resolved photoelectron imaging.

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9

Geue, RJ, P. Osvath, AM Sargeson, KR Acharya, SB Noor, TNG Row, and K. Venkatesan. "The Reaction of a Nitro-Capped Cobalt(III) Cage Complex With Base: the Crystal Structure of a Contracted Cage Complex, and the Mechanism of Its Formation." Australian Journal of Chemistry 47, no. 3 (1994): 511. http://dx.doi.org/10.1071/ch9940511.

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The synthesis, properties and crystal structure of the cage complex (1-hydroxy-8-methyl-3,6,10,13,15,18-hexaazabicyclo[6.6.5] nonadecane )cobalt(III) chloride hydrate ([Co( Me,OH-absar )]Cl3.H2O) are reported. The mechanism of the formation of this contracted cavity cage from a nitro-capped hexaazabicycloicosane type cage has been investigated. Treatment of (1- methyl-8-nitro-3,6,10,13,16,19-hexaazabicyclo[6.6.6] icosane )cobalt(III) chloride ([Co(Me,NO2- sar )]3+) with excess base in aqueous solution leads initially to rapid (t½. < 1 ms) and reversible deprotonation of one coordinated secondary amine. This species undergoes a retro-Mannich type reaction and imine hydrolysis (t½ ≈ 90 s). Quenching the reaction with acid gives rise to a pair of isomeric intermediate species which have been isolated and characterized. They have a pendant arm macrocyclic structure, resulting from the loss of a methylene unit from one of the arms of the cap. Heating either isomer in aqueous solution gives the new cage compound with the contracted cap. It is postulated that this occurs through a Nef reaction, resulting in the formation of a ketone which then condenses with the coordinated primary amine. A comparison with the corresponding bicycloicosane analogue indicates a reduced chromophoric cavity size for the contracted cage. The reduction potential of the cobalt(III)/cobalt(II) couple is 170 mV more negative for the smaller cage, and, in the electronic spectrum of the cobalt(III) complex, the d-d transitions are both shifted to higher energy, corresponding to a stronger ligand field.

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10

Acharyya, Koushik, and Partha Sarathi Mukherjee. "Shape and size directed self-selection in organic cage formation." Chemical Communications 51, no. 20 (2015): 4241–44. http://dx.doi.org/10.1039/c5cc00075k.

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[3+2] self-assembly of an unsymmetrical aldehyde and a flexible amine yielded a single isomeric cage out of two possible isomeric cages. The experimental and theoretical findings suggest that the geometric features of the aldehyde play a key role in such self-selection.

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11

Chen, Gong-Jun, Chao-Qun Chen, Xue-Tian Li, Hui-Chao Ma, and Yu-Bin Dong. "Cu3L2 metal–organic cages for A3-coupling reactions: reversible coordination interaction triggered homogeneous catalysis and heterogeneous recovery." Chemical Communications 54, no. 82 (2018): 11550–53. http://dx.doi.org/10.1039/c8cc07208f.

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A novel Cu₃L₂ metal–organic cage, which features coordination interaction triggered solubility, can be a highly active and reusable catalyst to homogeneously catalyse the one-pot aldehyde–alkyne–amine A³-coupling reaction.

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12

Sargeson, Alan M., and Peter A. Lay. "Dependence of the Properties of Cobalt(III) Cage Complex as a Function of the Derivatization of Amine Substituents." Australian Journal of Chemistry 62, no. 10 (2009): 1280. http://dx.doi.org/10.1071/ch09368.

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Control of redox properties of cobalt macrobicyclic hexaamine (cage) complexes by substituent modification is important for their use as electron-transfer agents, and the resultant derivatives can also change the lipophilicity of the complexes for a variety of biological and other applications. Such derivatization is also important for incorporating cage complexes into a range of redoxactive conjugates. Here, the derivatization of the amine groups in the 1 and 8 positions of [Co(sar)]3+ (sar = sarcophagine = 3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane) are reported. The synthesis and properties of methylamide (from the reactions with acetic anhydride), arylimine (from Schiff base reactions), benzylamine, phthalimido, and tosylate derivatives are described. These reactions provide synthons that have the potential to act as precursors for building a range of conjugates containing metal cage complexes, including dimers. The effects of the substituents on the ligand conformations, which affect other chemical and physical properties of the cage complexes, are discussed.

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13

Pinto, Andrea, Giulia Spigolon, Raquel Gavara, Cristiano Zonta, Giulia Licini, and Laura Rodríguez. "Tripodal gold(i) polypyridyl complexes and their Cu+ and Zn2+ heterometallic derivatives. Effects on luminescence." Dalton Transactions 49, no. 41 (2020): 14613–25. http://dx.doi.org/10.1039/d0dt02564j.

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Tripodal Au(i) complexes of tris(2-pyridylmethyl)amine coordinated to Au–PR₃ moieties with open or cage-like structures have been synthesized and the changes on their resulting luminescence upon coordination to Zn²⁺ and Cu⁺-salts analyzed.

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14

Mdzinarishvili, Alexander, Werner J. Geldenhuys, Thomas J. Abbruscato, Ulrich Bickel, Jochen Klein, and Cornelis J. Van der Schyf. "NGP1-01, a lipophilic polycyclic cage amine, is neuroprotective in focal ischemia." Neuroscience Letters 383, no. 1-2 (July 2005): 49–53. http://dx.doi.org/10.1016/j.neulet.2005.03.042.

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15

Clark, IJ, II Creaser, LM Engelhardt, JM Harrowfield, ER Krausz, GM Moran, AM Sargeson, and AH White. "Synthesis, Structure and Redox Properties of Nickel Complexes of Cage Amine Ligands." Australian Journal of Chemistry 46, no. 1 (1993): 111. http://dx.doi.org/10.1071/ch9930111.

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The syntheses of complexes containing the [Ni( sar )]2+/3+ and [Ni((NH3)2sar)]4+ ions are described along with an X-ray crystal structure analysis of the salt [Ni((NH3)2sar)] (NO3)4.H2O ( sar is 3,6,10,13,16,19-hexaazabicyclo[6.6.6] icosane ; (NH3)2sar2+ is its 1,8-diammonio derivative). The NiIII ion is a powerful oxidant, with E′ = 0.90 V (v. n.h.e. at 298 K, I = 0.2, aqueous trifluoromethanesulfonate medium), but is relatively stable in dilute aqueous acid. Both the NiII and NiIII complexes of sar have been resolved into their enantiomeric forms, and their absorption, optical rotatory dispersion and circular dichroism spectra recorded and partly analysed. The electron self-exchange rate between enantiomeric forms in the different oxidation states has been measured by a stopped-flow circular dichroism method, and ket = (5.3�0.3)×103 dm3 mol-1 s-1 at 298 K, I = 0.2 (NaCF3SO3). The activation parameters, ΔH‡ 22�4 kJ mol-1 and ΔS‡ -100�12 J K-1 mol-1, and the rate constants are consistent with the comparatively small rearrangements required in the structures of the two ions relative to the optimal cavity radius for the cage of 2.05(1) Ǻ.

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16

Comba, Peter, Lutz M. Engelhardt, Jack MacB Harrowfield, Geoffrey A. Lawrance, Lisandra L. Martin, Alan M. Sargeson, and Allan H. White. "Synthesis and characterization of a stable hexa-amine vanadium(IV) cage complex." Journal of the Chemical Society, Chemical Communications, no. 3 (1985): 174. http://dx.doi.org/10.1039/c39850000174.

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17

Paterson, Brett M., Gojko Buncic, Lachlan E. McInnes, Peter Roselt, Carleen Cullinane, David S. Binns, Charmaine M. Jeffery, Roger I. Price, Rodney J. Hicks, and Paul S. Donnelly. "Bifunctional 64Cu-labelled macrobicyclic cage amine isothiocyanates for immuno-positron emission tomography." Dalton Transactions 44, no. 11 (2015): 4901–9. http://dx.doi.org/10.1039/c4dt02983f.

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18

Edward, John T., Francis L. Chubb, Denis FR Gilson, Rosemary C. Hynes, Françoise Sauriol, and Alain Wiesenthal. "Article." Canadian Journal of Chemistry 77, no. 5-6 (June 1, 1999): 1057–65. http://dx.doi.org/10.1139/v99-118.

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Three new cage peroxides, 1,6-diaza-3,4,8,9-tetraoxabicyclo[4.4.2]dodecane (3a),1,6-diaza-3,4,8,9-tetraoxa-11-methylbicyclo[4.4.2]dodecane (3b), and 1,6-diaza-3,4,8,9-tetraoxatricyclo[4.4.2.411,12]hexadecane (4), have been prepared by reaction of 1,2-diaminoethane, 1,2-diaminopropane, and trans-1,2-diaminocyclohexane, respectively, with formaldehyde and hydrogen peroxide in aqueous acidic solution. Their structures have been established by X-ray diffraction, and show the bridgehead nitrogen atoms to be predominantly sp2 hybridized. The structures accord with 1H and 13C NMR spectra. Variable temperature NMR studies show that the diperoxide 3a begins to undergo rapid inversion (on the NMR time scale) at about 303 K; up to 370 K the diperoxides 3b and 4 show no conformational change.Key words: cage compounds, formaldehyde, peroxides, amine nitrogen, hybridization.

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19

Ling, Irene, Alexandre N. Sobolev, Rauzah Hashim, and Jack M. Harrowfield. "Stereochemistry of cage amine complexes – probing the ligand conformational flexibility with hydrogen bonds." CrystEngComm 16, no. 48 (2014): 11058–63. http://dx.doi.org/10.1039/c4ce01980f.

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Structure determinations for some Co(iii) sarcophagine complexes show that there is no evidence that the H-bonding involving the NH centres of the complex cations is influenced by electronic effects due to the substituents.

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20

Morozov, Boris S., Siva S. R. Namashivaya, Marina A. Zakharko, Aleksandr S. Oshchepkov, and Evgeny A. Kataev. "Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions." ChemistryOpen 9, no. 2 (December 4, 2019): 171–75. http://dx.doi.org/10.1002/open.201900309.

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21

Morozov, Boris S., Siva S. R. Namashivaya, Marina A. Zakharko, Aleksandr S. Oshchepkov, and Evgeny A. Kataev. "Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions." ChemistryOpen 9, no. 2 (January 30, 2020): 99. http://dx.doi.org/10.1002/open.202000009.

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22

Yao, Yuan, Jingya Li, Yanyan Zhou, Ting Gao, Hongfeng Li, and Pengfei Yan. "Turn-on luminescence detection of biogenic amine with an Eu(III) tetrahedron cage." Dyes and Pigments 192 (August 2021): 109441. http://dx.doi.org/10.1016/j.dyepig.2021.109441.

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23

Sapchenko, Sergey A., Danil N. Dybtsev, and Vladimir P. Fedin. "Cage amines in the metal–organic frameworks chemistry." Pure and Applied Chemistry 89, no. 8 (July 26, 2017): 1049–64. http://dx.doi.org/10.1515/pac-2016-1206.

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AbstractNitrogen-rich porous materials have outstanding gas sorption and separation capacity. Using cage amines in the synthesis of metal–organic frameworks is a simple approach for generating the free nitrogen donor centers within the channels of porous materials without the post-synthetic modification. 1,4-Diazabicyclo[2.2.2]octane has a linear arrangement of nitrogen centers and can be used as a linear linker for the design of porous MOF materials. Urotropine has four nitrogen atoms and can act as a tetrahedral four-connected, pyramidal three-connected or bent two-connected linker. Such a diversity of coordination possibilities enriches the structural chemistry of MOFs and allows obtaining the frameworks with unique secondary building units and topology. The presence of cage amines in the structure affects the sorption characteristics of the materials. They demonstrate high selectivity to CO2 and can participate as a heterogeneous base catalyst in the organic reactions. Besides that the cage-amine based metal–organic frameworks demonstrate photoluminescent properties and can be used as nanoreactors for photochemical transformations. These compounds are also an important object of thermodynamic studies helping us better understand the nature of host–guest interaction in the supramolecular systems.

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24

Qiu, Gege, Djamel Eddine Khatmi, Alexandre Martinez, and Paola Nava. "Rationalization of chirality transfer and fast conformational changes in a tris(2-pyridylmethyl)amine-based cage." RSC Advances 11, no. 23 (2021): 13763–68. http://dx.doi.org/10.1039/d1ra01761f.

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25

Harrowfield, Jack M., George A. Koutsantonis, Nigel A. Lengkeek, Brian W. Skelton, and Allan H. White. "Structural and Electrochemical Studies of Co(III) Cage Amine Complexes with Pendent Thienylmethylamino Groups." Inorganic Chemistry 49, no. 7 (April 5, 2010): 3152–61. http://dx.doi.org/10.1021/ic9019603.

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26

Diaz, Martin, Jojo Jaballas, Dan Tran, Hans Lee, Joachin Arias, and Thomas Onak. "Interaction of Trimethylamine andcloso-1,6-C2B7H9. Evidence for an “Open” Cage C2B7H9/Amine Adduct." Inorganic Chemistry 35, no. 16 (January 1996): 4536–40. http://dx.doi.org/10.1021/ic960254e.

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27

Kawakami, Yoshiteru, Kazuo Yamaguchi, Tsutomu Yokozawa, Takanori Serizawa, Minoru Hasegawa, and Yoshio Kabe. "Higher Polyhedral Silsesquioxane (POSS) Cage by Amine-catalyzed Condensation of Silanols and Related Siloxanes." Chemistry Letters 36, no. 6 (June 5, 2007): 792–93. http://dx.doi.org/10.1246/cl.2007.792.

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28

Qiu, Gege, Paola Nava, Alexandre Martinez, and Cédric Colomban. "A tris(benzyltriazolemethyl)amine-based cage as a CuAAC ligand tolerant to exogeneous bulky nucleophiles." Chemical Communications 57, no. 18 (2021): 2281–84. http://dx.doi.org/10.1039/d0cc08005e.

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The canonical CuAAC–ligand TBTA was capped with a bowl-shaped unit yielding the cage Hm-TBTA. The shielded structure does not suffer from product inhibition effect and is remarkably tolerant to the biological CuAAC-inhibitor Glutathione.

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29

Osvath, P., and AM Sargeson. "Ring Opening and Rearrangement of a Nitro-Capped Cobalt(III) Cage Complex With an N3S3 Donor Set." Australian Journal of Chemistry 47, no. 5 (1994): 807. http://dx.doi.org/10.1071/ch9940807.

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Treatment of the N3S3 donor cage complex [Co(NO2-capten)]3+ (1-methyl-8-nitro-3,13,16-trithia-6,10,19-triazabicyclo[6.6.6]icosanecobalt(III)) with excess base leads to deprotonation of a secondary coordinated amine group, followed by loss of a methylene unit from the cap by a retro-Mannich type reaction. Subsequent intermolecular hydride transfer gives a novel oxidized and partly delocalized macrocyclic complexed carbanion (13-(4-amino-2-thiabutyl)-13-methyl-6-nitro-1,11-dithia-4,8-diazacyclotetradec-4-enato(6)cobalt(III)) that is stabilized by deprotonation, and which remains deprotonated even in strong acid.

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30

Paterson, Brett M., Peter Roselt, Delphine Denoyer, Carleen Cullinane, David Binns, Wayne Noonan, Charmaine M. Jeffery, et al. "PET imaging of tumours with a64Cu labeled macrobicyclic cage amine ligand tethered to Tyr3-octreotate." Dalton Trans. 43, no. 3 (2014): 1386–96. http://dx.doi.org/10.1039/c3dt52647j.

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31

Štíbr, Bohumil. "Acyl chloride carbon insertion into dicarbaborane cages – new route to tricarbollide cages." Pure and Applied Chemistry 87, no. 2 (February 1, 2015): 135–42. http://dx.doi.org/10.1515/pac-2014-0937.

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AbstractReactions between the arachno-6,9-C2B8H14 dicarbaborane and acyl chlorides, RCOCl, in the presence of amine bases in CH2Cl2, followed by acidification with conc. H2SO4 at 0 °C, generate in high yields a series of neutral alkyl and aryl tricarbollides of structure 8-R-nido-7,8,9-C3B8H11 (where R=alkyls and aryls). These skeletal alkylcarbonation (SAC) reactions are consistent with an aldol-type condensation between the RCO group and open-face dicarbaborane hydrogen atoms, which is associated with the insertion of the acyl chloride RC unit into the structure under elimination of three extra hydrogen atoms as H2O and HCl. The reactions thus result in an effective cross-coupling between R and the tricarbollide cage. High-temperature reactions between 8-Ar-nido-7,8,9-C3B8H11 (where Ar=Ph, 1-C10H7, and 2-C10H7) compounds and [CpFe(CO)2]2 produced the first types of monoaryl substituted twelve-vertex ferratricarbollide complexes of general constitution [1-(CpFe)-closo-ArC3B8H10] with three different arrangements of cluster carbon vertexes. The Fe-complexation is accompanied by extensive rearrangement of the cluster carbon atoms over the twelve-vertex cage and the complexes isolated can be regarded as ferrocene analogues.

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32

Qiu, Gege, Cédric Colomban, Nicolas Vanthuyne, Michel Giorgi, and Alexandre Martinez. "Chirality transfer in a cage controls the clockwise/anticlockwise propeller arrangement of the tris(2-pyridylmethyl)amine ligand." Chemical Communications 55, no. 94 (2019): 14158–61. http://dx.doi.org/10.1039/c9cc07244f.

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A predictable control of the propeller arrangement of the tris(2-pyridylmethyl)amine (TPA) ligand was achieved in the smallest hemicryptophane 1. Coordination of Cu(i) result in a rare T-shaped complex with controlled helicity of the TPA-Cu core.

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33

Vasylevskyi, Serhii, Anja Holzheu, and Katharina M. Fromm. "Solid-state structure and antimicrobial and cytotoxicity studies of a cucurbit[6]uril-like Cu6 L 4 constructed from 3,5-bis[(1H-tetrazol-5-yl)methyl]-4H-1,2,4-triazol-4-amine." Acta Crystallographica Section C Structural Chemistry 74, no. 11 (October 18, 2018): 1413–19. http://dx.doi.org/10.1107/s2053229618013670.

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3,5-Bis[(1H-tetrazol-5-yl)methyl]-4H-1,2,4-triazol-4-amine (H2 L) associates under deprotonation with CuSO4 in aqueous medium to form a new waisted barrel-shaped M 6 L 4 cluster, namely hexaaquatetrakis{μ4-3,5-bis[(1H-tetrazol-5-yl)methyl]-4H-1,2,4-triazol-4-amine}-μ4-sulfato-hexacopper(II) sulfate hydrate, [Cu6(SO4)(C6H6N12)4(H2O)6]SO4·nH2O (n = ∼23) (1). Cluster 1 resembles concave cucurbit[6]uril and has one disordered sulfate anion trapped inside the cage, which additionally stabilizes the Cu6 unit. The CuII ions have either a square-pyramidal or a distorted octahedral geometry. The equatorial positions are filled by N atoms from the L 2− ligand, while the axial positions are occupied by coordinated water molecules and O atoms of the sulfate counter-ion. In the solid state, the Cu6 clusters are connected through a large number of hydrogen bonds formed by uncoordinated water molecules and an additional sulfate anion. The compound shows good antimicrobial activity against E. coli tested with the Kirby Bauer approach. In addition, the cell viability towards HeLa and L-929 cells was studied.

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34

Lockman, J. A., W. J. Geldenhuys, M. R. Jones-Higgins, J. D. Patrick, D. D. Allen, and C. J. Van der Schyf. "NGP1-01, a multi-targeted polycyclic cage amine, attenuates brain endothelial cell death in iron overload conditions." Brain Research 1489 (December 2012): 133–39. http://dx.doi.org/10.1016/j.brainres.2012.10.029.

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35

Budi Hartono, Sandy, ShiZhang Qiao, Kevin Jack, Bradley P. Ladewig, Zhengping Hao, and GaoQing (Max) Lu. "Improving Adsorbent Properties of Cage-like Ordered Amine Functionalized Mesoporous Silica with Very Large Pores for Bioadsorption." Langmuir 25, no. 11 (June 2, 2009): 6413–24. http://dx.doi.org/10.1021/la900023p.

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36

Lay, PA, J. Lydon, AWH Mau, P. Osvath, AM Sargeson, and WHF Sasse. "The Synthesis and Properties of Cobalt Cage Complexes With N3S3 Donor Sets." Australian Journal of Chemistry 46, no. 5 (1993): 641. http://dx.doi.org/10.1071/ch9930641.

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An understanding of how variations in the cage ligands modify the redox behaviour of cobalt(II)/(III) couples has led to rational syntheses of a series N3S3 donor cobalt cage complexes that have redox potentials and electron self-exchange rates appropriate for their use as electron carriers in systems devised for the photoreduction of water. Diazotization of [Co(NH3-capten)]Cl4 (NH3-capten = 8-ammonio-1-methyl-3,13,16-trithia-6,10,19-triazabicyclo[6.6.6] icosane ) in nitric acid resulted in a mixture of five complexes: [Co(NO2-capten)]3+, [Co( Cl-capten )]3+ and [Co(HO- capten )]3+ (8-nitro-, 8-chloro- and 8-hydroxy-1-methyl-3,13,16-trithia-6,10,19-triazabicyclo[6.6.6] icosanecobalt (III) respectively), in which the cage framework remained intact, together with two complexes with a contracted cap, [Co(ClCH2-abcapten)]3+ and [Co(HOCH2-abcapten)]3+, (8-chloromethyl- and 8-hydroxymethyl-1-methyl-3,13,16-trithia-6,10,19-triazabicyclo[6.6.5] nonadecanecobalt (III), respectively). Reductive elimination occurred with [Co( Cl-capten )]3+ in the presence of Zn or Ni/Al alloy to give the parent cage complex, [Co( capten )]3+ (1-methyl-3,13,16-trithia-6,10,19-triazabicyclo[6.6.6] icosanecobalt (III)). When [Co(ten)]3+(4,4′,4″-ethylidynetris(3-thiabutan-1-amine)cobalt(III)) and an aqeuous solution of diethyl malonate and formaldehyde were reacted under basic conditions, the amide cage complex, [Co( EtOOC-oxocapten-H )]2+, (8-ethoxycarbonyl-1-methyl-3,13,16-trithia-6,10,19-triazabicyclo [6.6.6]icosan-7-onato(1-)cobalt(III)) was obtained. Hydrolysis of the ester group in base yielded the carboxylate derivative [Co(OOC- oxocapten - H)]+(8-carboxylate-1-methyl-3,13,16-trithia-6,10,19-triazabicyclo[6.6.6]icosan-7-onato(1-)cobalt(III)). The complexes were characterized by microanalyses, 1H and 13C n.m.r. spectroscopy, and electrochemistry. The values of the cobalt(III)/(II) redox potentials change with the nature of the apical substituents in a similar manner to that observed for the analogous hexaamine cage complexes, but they are all more positive, and the cobalt(II) complexes are low spin. The N3S3 donor set stabilizes the lower oxidation state and the low-spin electronic configuration. All of these cage complexes are effective at quenching the lowest lying triplet excited state of the [ Ru ( bpy )3]2+ complex, with rate constants typically c. 109 dm3 mol-1s-1. [Co( EtOOC-oxocapten-H )]2+ quenches [ Ru*( bpy )3]2+ very efficiently and has a suitable redox potential for hydrogen production, but it is only moderately efficient as an electron-transfer agent in the photoreduction of water. It is apparent that the high molar absorption coefficients of these cage complexes in the visible region, the too positive redox potentials and competing energy transfer and/or back electron-transfer inhibit their ability to be used as effective electron-transfer agents in these reactions at pH c. 5. However, the molecules are inherently interesting and stable redox reagents which undergo rapid one-electron reactions.

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37

Goez, Martin, Isabell Frisch, and Ingo Sartorius. "Electron and hydrogen self-exchange of free radicals of sterically hindered tertiary aliphatic amines investigated by photo-CIDNP." Beilstein Journal of Organic Chemistry 9 (February 26, 2013): 437–46. http://dx.doi.org/10.3762/bjoc.9.46.

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The photoreactions of diazabicyclo[2,2,2]octane (DABCO) and triisopropylamine (TIPA) with the sensitizers anthraquinone (AQ) and xanthone (XA) or benzophenone (BP) were investigated by time-resolved photo-CIDNP (photochemically induced dynamic nuclear polarization) experiments. By varying the radical-pair concentration, it was ensured that these measurements respond only to self-exchange reactions of the free amine-derived radicals (radical cations DH • + or α-amino alkyl radicals D • ) with the parent amine DH; the acid–base equilibrium between DH • + and D • also plays no role. Although the sensitizer does not at all participate in the observed processes, it has a pronounced influence on the CIDNP kinetics because the reaction occurs through successive radical pairs. With AQ, the polarizations stem from the initially formed radical-ion pairs, and escaping DH • + then undergoes electron self-exchange with DH. In the reaction sensitized with XA (or BP), the polarizations arise in a secondary pair of neutral radicals that is rapidly produced by in-cage proton transfer, and the CIDNP kinetics are due to hydrogen self-exchange between escaping D • and DH. For TIPA, the activation parameters of both self-exchange reactions were determined. Outer-sphere reorganization energies obtained with the Marcus theory gave very good agreement between experimental and calculated values of ∆G ‡ 298.

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38

Morozov, Boris S., Siva S. R. Namashivaya, Marina A. Zakharko, Aleksandr S. Oshchepkov, and Evgeny A. Kataev. "Front Cover: Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions (ChemistryOpen 2/2020)." ChemistryOpen 9, no. 2 (January 28, 2020): 97. http://dx.doi.org/10.1002/open.202000010.

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39

Youn, Yeobum, Jiwoong Seol, Minjun Cha, Yun-Ho Ahn, and Huen Lee. "Structural Transition Induced by CH4 Enclathration and Cage Expansion with Large Guest Molecules Occurring in Amine Hydrate Systems." Journal of Chemical & Engineering Data 59, no. 6 (May 19, 2014): 2004–12. http://dx.doi.org/10.1021/je500167n.

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40

Deryabin, Dmitry G., Olga K. Davydova, Zulfiya ZH Yankina, Alexey S. Vasilchenko, Sergei A. Miroshnikov, Alexey B. Kornev, Anastasiya V. Ivanchikhina, and Pavel A. Troshin. "The Activity of [60]Fullerene Derivatives Bearing Amine and Carboxylic Solubilizing Groups againstEscherichia coli: A Comparative Study." Journal of Nanomaterials 2014 (2014): 1–9. http://dx.doi.org/10.1155/2014/907435.

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We report a comparative investigation of the antibacterial activity of two water-soluble fullerene derivatives bearing protonated amine (AF) and deprotonated carboxylic (CF) groups appended to the fullerene cage via organic linkers. The negatively charged fullerene derivative CF showed no tendency to bind to the bacterial cells and, consequently, no significant antibacterial activity. In contrast, the compound AF loaded with cationic groups showed strong and partially irreversible binding to the negatively chargedEscherichia coliK12 TG1 cells and to human erythrocytes, also possessing negative zeta potential. Adsorption of AF on the bacterial surface was visualized by atomic force microscopy revealing the formation of specific clusters (AF aggregates) surrounding the bacterial cell. Incubation ofE. coliK12 TG1 with AF led to a dose-dependent bactericidal effect withLD50 = 79.1 µM. The presence of human erythrocytes in the test medium decreased the AF antibacterial activity. Thus we reveal that the water-soluble cationic fullerene derivative AF possesses promising antibacterial activity, which might be utilized in the development of novel types of chemical disinfectants.

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41

Gahan, LR, TW Hambley, and PC Healy. "Dithiocarbamates as Innocent Anions: The Synthesis and Structural Properties of (8-Methyl-3,6,10,13,16,19-hexaazabicyclo[6.6.6]-icosan-1-amine)cobalt(Ii I) Tris(N,N-diethyldithiocarbamate), [Co(AMMEsar)][Et2dtc]3." Australian Journal of Chemistry 41, no. 5 (1988): 635. http://dx.doi.org/10.1071/ch9880635.

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Sodium diethyldithiocarbamate, Na[Et2dtc], reacts with (8-methyl-3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosan-1-aminium)cobalt(III) chloride, [Co( AMMEsarH )]Cl4, in aqueous solution to form the compound [Co( AMMEsar )][Et2dtc]3 which is readily soluble in organic solvents. Crystals are trigonal, space group R3c (3m, No. 167) with a 13.864(4), c 36.42(2)Ǻ, Z 6. A full-matrix least-squares refinement on 952 reflections, with I > 2.5σ(I), converged with final R of 0.037. The structure consists of the [Co( AMMEsar )]3+ cation and three [Et2dtc]- anions. The primary aminium group on one trigonal cap of the cage is deprotonated to an amine. Strong hydrogen bonds exist between the sulfur atoms of the diethyldithiocarbamate anions and the protons of the secondary amines of the complex cation, which is stabilized in the lel conformation.

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42

Ma, Michelle T., Oliver C. Neels, Delphine Denoyer, Peter Roselt, John A. Karas, Denis B. Scanlon, Jonathan M. White, Rodney J. Hicks, and Paul S. Donnelly. "Gallium-68 Complex of a Macrobicyclic Cage Amine Chelator Tethered to Two Integrin-Targeting Peptides for Diagnostic Tumor Imaging." Bioconjugate Chemistry 22, no. 10 (October 19, 2011): 2093–103. http://dx.doi.org/10.1021/bc200319q.

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43

Yao, Yuan, Yanyan Zhou, Tianyu Zhu, Ting Gao, Hongfeng Li, and Pengfei Yan. "Eu(III) Tetrahedron Cage as a Luminescent Chemosensor for Rapidly Reversible and Turn-On Detection of Volatile Amine/NH3." ACS Applied Materials & Interfaces 12, no. 13 (March 9, 2020): 15338–47. http://dx.doi.org/10.1021/acsami.9b21425.

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44

Ma, Michelle T., John A. Karas, Jonathan M. White, Denis Scanlon, and Paul S. Donnelly. "A new bifunctional chelator for copper radiopharmaceuticals: a cage amine ligand with a carboxylate functional group for conjugation to peptides." Chemical Communications, no. 22 (2009): 3237. http://dx.doi.org/10.1039/b903426a.

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45

Harrowfield, JM, Y. Kim, BW Skelton, and AH White. "Mixed Transition Metal/Lanthanide Complexes: Structural Characterization of Solids Containing Cage Amine Chromium(III) Cations and Tris(dipicolinato)lanthanide Anions." Australian Journal of Chemistry 48, no. 4 (1995): 807. http://dx.doi.org/10.1071/ch9950807.

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As the foundation to a survey of interactions between chromium(III) and lanthanide(III) ions within the same crystal lattice, a series of complexes of stoichiometry [Cr((NH2)2sar)]- [ Ln ( dipic )3].8H2O (sar = 3,6,10,13,16,19-hexaazabicyclo[6.6.6] icosane, Ln = La-Lu plus Y, dipic = pyridine-2,6-dicarboxylate) has been synthesized and structurally characterized by room-temperature single-crystal X-ray studies. An isomorphous series is found for all Ln, being triclinic, Pī , a ≈ 18.1, b ≈ 13.3, c ≈ 11 Ǻ, α ≈ 111.5, β ≈ 96.2, γ ≈ 109.2°, Z = 2 formula units, full structure determinations being recorded for Ln = La (conventional R 0.048 on |F| for No 6494 independent 'observed' [I > 3σ(I)] reflections at convergence), Ce (R 0.036 for No 8980) and Lu (R 0.046 for No 6791). A less well defined protonated series, with a 2:3 Cr/ Ln ratio, has also been characterized specifically for Ln = La [orthorhombic, Pbca , a 26.223(8), b 53.17(3), c 18.329(9) Ǻ, Z = 8; R 0.092 for No 5104], the lutetium analogue having a similar cell.

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46

Pulido, Angeles, Ming Liu, Paul Reiss, Anna Slater, Sam Chong, Marc Little, Tom Hasell, Mike Briggs, Andrew Cooper, and Graeme Day. "Towards computer-guided tuning of the crystal packing of porous organic cages." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C667. http://dx.doi.org/10.1107/s2053273314093322.

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Among microporous materials, there has been an increasing recent interest in porous organic cage (POC) crystals, which can display permanent intrinsic (molecular) and extrinsic (crystal network) porosity. These materials can be used as molecular sieves for gas separation and potential applications as enzyme mimics have been suggested since they exhibit structural response toward guest molecules[1]. Small structural modifications of the initial building blocks of the porous organic molecules can lead to quite different molecular assembly[1]. Moreover, the crystal packing of POCs is based on weak molecular interactions and is less predictable that other porous materials such as MOFs or zeolites.[2] In this contribution, we show that computational techniques -molecular conformational searches and crystal structure prediction- can be successfully used to understand POC crystal packing preferences. Computational results will be presented for a series of closely related tetrahedral imine- and amine-linked porous molecules, formed by [4+6] condensation of aromatic aldehydes and cyclohexyl linked diamines. While the basic cage is known to have one strongly preferred crystal structure, the presence of small alkyl groups on the POC modifies its crystal packing preferences, leading to extensive polymorphism. Calculations were able to successfully identify these trends as well as to predict the structures obtained experimentally, demonstrating the potential for computational pre-screening in the design of POCs within targeted crystal structures. Moreover, the need of accurate molecular (ab initio calculations) and crystal (based on atom-atom potential lattice energy minimization) modelling for computer-guided crystal engineering will be discussed.

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47

Magerstadt, M., R. Bruce King, M. G. Newton, N. E. Tonks, and C. E. Ringold. "Preparation of a novel sulfur-nitrogen cage compound by the transamination of bis(dimethylamino) sulfide with a macrocyclic tetra(secondary amine)." Journal of the American Chemical Society 108, no. 4 (February 1986): 850–51. http://dx.doi.org/10.1021/ja00264a055.

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48

Liu, Ming, Marc A. Little, Kim E. Jelfs, James T. A. Jones, Marc Schmidtmann, Samantha Y. Chong, Tom Hasell, and Andrew I. Cooper. "Acid- and Base-Stable Porous Organic Cages: Shape Persistence and pH Stability via Post-synthetic “Tying” of a Flexible Amine Cage." Journal of the American Chemical Society 136, no. 21 (May 13, 2014): 7583–86. http://dx.doi.org/10.1021/ja503223j.

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49

Springborg, Johan, Ulla Pretzmann, Carl Erik Olsen, Kim Simonsen, György Liptay, Katrin Trautwein-Fritz, Joseph Stackhouse, et al. "An Inert Proton Coordinated Inside the Tetrahedral Cage [3 6]Adamanzane. Synthesis of the Inside Monoprotonated Amine 1,5,9,13-Tetraazatricyclo[7.7.3.3(5,13)]docosane." Acta Chemica Scandinavica 50 (1996): 294–98. http://dx.doi.org/10.3891/acta.chem.scand.50-0294.

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50

Alt, Karen, Brett M. Paterson, Katie Ardipradja, Christine Schieber, Gojko Buncic, Bock Lim, Stan S. Poniger, et al. "Single-Chain Antibody Conjugated to a Cage Amine Chelator and Labeled with Positron-Emitting Copper-64 for Diagnostic Imaging of Activated Platelets." Molecular Pharmaceutics 11, no. 8 (July 14, 2014): 2855–63. http://dx.doi.org/10.1021/mp500209a.

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