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Journal articles on the topic 'Macrocyclic cyclophanes'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

Collins, Shawn K., and Yassir El-Azizi. "Development of quadrupolar engaging auxiliaries as novel gearing elements for macrocyclization." Pure and Applied Chemistry 78, no. 4 (January 1, 2006): 783–89. http://dx.doi.org/10.1351/pac200678040783.

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The formation of various macrocyclic cyclophanes via ring-closing olefin metathesis is possible through the use of a pendant pentafluorobenzyl ester group. A quadrupolar interaction between the cyclophane core and the auxiliary is proposed to act as a gearing element facilitating cyclization. The development of these noncovalent interactions as gearing elements as well as the investigation of the effect of the site of metathesis upon the macrocyclization process is described.

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2

Salazar-Medina, Alex J., Enrique F. Velazquez-Contreras, Rocio Sugich-Miranda, Hisila Santacruz, Rosa E. Navarro, Fernando Rocha-Alonzo, Maria A. Islas-Osuna, et al. "Immune response of human cultured cells towards macrocyclic Fe2PO and Fe2PC bioactive cyclophane complexes." PeerJ 8 (April 20, 2020): e8956. http://dx.doi.org/10.7717/peerj.8956.

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Synthetic molecules that mimic the function of natural enzymes or molecules have untapped potential for use in the next generation of drugs. Cyclic compounds that contain aromatic rings are macrocyclic cyclophanes, and when they coordinate iron ions are of particular interest due to their antioxidant and biomimetic properties. However, little is known about the molecular responses at the cellular level. This study aims to evaluate the changes in immune gene expression in human cells exposed to the cyclophanes Fe2PO and Fe2PC. Confluent human embryonic kidney cells were exposed to either the cyclophane Fe2PO or Fe2PC before extraction of RNA. The expression of a panel of innate and adaptive immune genes was analyzed by quantitative real-time PCR. Evidence was found for an inflammatory response elicited by the cyclophane exposures. After 8 h of exposure, the cells increased the relative expression of inflammatory mediators such as interleukin 1; IRAK, which transduces signals between interleukin 1 receptors and the NFκB pathway; and the LPS pattern recognition receptor CD14. After 24 h of exposure, regulatory genes begin to counter the inflammation, as some genes involved in oxidative stress, apoptosis and non-inflammatory immune responses come into play. Both Fe2PO and Fe2PC induced similar immunogenetic changes in transcription profiles, but equal molar doses of Fe2PC resulted in more robust responses. These data suggest that further work in whole animal models may provide more insights into the extent of systemic physiological changes induced by these cyclophanes.

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3

Monchaud, David, Anton Granzhan, Nicolas Saettel, Aurore Guédin, Jean-Louis Mergny, and Marie-Paule Teulade-Fichou. "“One Ring to Bind Them All”—Part I: The Efficiency of the Macrocyclic Scaffold for G-Quadruplex DNA Recognition." Journal of Nucleic Acids 2010 (2010): 1–19. http://dx.doi.org/10.4061/2010/525862.

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Macrocyclic scaffolds are particularly attractive for designing selective G-quadruplex ligands essentially because, on one hand, they show a poor affinity for the “standard” B-DNA conformation and, on the other hand, they fit nicely with the external G-quartets of quadruplexes. Stimulated by the pioneering studies on the cationic porphyrin TMPyP4 and the natural product telomestatin, follow-up studies have developed, rapidly leading to a large diversity of macrocyclic structures with remarkable-quadruplex binding properties and biological activities. In this review we summarize the current state of the art in detailing the three main categories of quadruplex-binding macrocycles described so far (telomestatin-like polyheteroarenes, porphyrins and derivatives, polyammonium cyclophanes), and in addressing both synthetic issues and biological aspects.

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4

Seliger, Piotr, Danuta Tomczyk, Grzegorz Andrijewski, and Ewa Tomal. "The Determination of Protonation Constants of Peptidomimetic Cyclophanes in Binary Methanol-Water Mixtures." Journal of Analytical Methods in Chemistry 2016 (2016): 1–7. http://dx.doi.org/10.1155/2016/1721069.

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The protonation constants of new group of peptidomimetic cyclophanes with valine or phenylalanine moieties incorporated into the macrocyclic skeleton as well as their linear analogues were determined by potentiometric measurements in solutions of methanol-water mixtures at 25°C and constant ionic strength. The influence of cavity size, location of protonation sites, and attached substituents of the macrocyclic ligands on the protonation constants were discussed on the basis of potentiometric measurement as well as H1-NMR results.

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5

Liu, Zhichang, Siva Krishna Mohan Nalluri, and J. Fraser Stoddart. "Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes." Chemical Society Reviews 46, no. 9 (2017): 2459–78. http://dx.doi.org/10.1039/c7cs00185a.

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6

Heerklotz, Joerg A., Changchun Fu, Anthony Linden, and Manfred Hesse. "ChemInform Abstract: Photochemical Ring Enlargement of Macrocyclic N-Phenyl Imides into Cyclophanes." ChemInform 31, no. 47 (November 21, 2000): no. http://dx.doi.org/10.1002/chin.200047157.

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7

Esteve, Ferran, Belen Altava, Michael Bolte, M. Isabel Burguete, Eduardo García-Verdugo, and Santiago V. Luis. "Highly Selective Anion Template Effect in the Synthesis of Constrained Pseudopeptidic Macrocyclic Cyclophanes." Journal of Organic Chemistry 85, no. 2 (December 20, 2019): 1138–45. http://dx.doi.org/10.1021/acs.joc.9b03048.

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8

Murakami, Yukito, Osamu Hayashida, and Yasuyuki Nagai. "Hybrid molecular assemblies in combinations of a synthetic peptide lipid with macrocyclic cyclophanes." Recueil des Travaux Chimiques des Pays-Bas 113, no. 4 (September 2, 2010): 209–15. http://dx.doi.org/10.1002/recl.19941130408.

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9

Bedi, Anjan, Linda J. W. Shimon, Benny Bogoslavsky, and Ori Gidron. "Easier to Twist than Bend: The Scope of the Bridge Formation Approach to Naphthalenophane Synthesis." Organic Materials 02, no. 04 (October 2020): 323–29. http://dx.doi.org/10.1055/s-0040-1721102.

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Twisting anthracene and higher acenes can alter their optical, magnetic, and electronic properties. To test the effect of twisting on the lower homologue, naphthalene, we synthesized tethered naphthalenophanes bearing alkyl bridges. Both X-ray structure and DFT calculations show that hexyl and butyl bridges induce a 6° and 12° end-to-end twist on the naphthalene unit, respectively. Attempts to increase the twisting further using shorter tethers resulted in an elimination product. Enantiomerically pure naphthalenophanes display strong chiroptical properties, which intensify with increasing twist. Attempts to induce bending, rather than twisting, using the same synthetic methodology, resulted in intermolecular dimerization, yielding macrocyclic naphthalenes. This work highlights the importance of steric hindrance in the synthesis of curved cyclophanes using the bridge formation approach.

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10

Miyake, Yoshihiro, Mo Wu, M. Jalilur Rahman, Yoshiyuki Kuwatani, and Masahiko Iyoda. "Efficient Construction of Biaryls and Macrocyclic Cyclophanes via Electron-Transfer Oxidation of Lipshutz Cuprates." Journal of Organic Chemistry 71, no. 16 (August 2006): 6110–17. http://dx.doi.org/10.1021/jo0608063.

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11

Murakami, Yukito, Jun-ichi Kikuchi, Masashi Suzuki, and Takeo Matsuura. "Syntheses of macrocyclic enzyme models. Part 6. Preparation and guest-binding behaviour of octopus cyclophanes." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1988): 1289. http://dx.doi.org/10.1039/p19880001289.

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12

Merzhyievskyi, D. O., O. V. Shablykin, O. V. Shablykina, N. M. Shevchenko, and V. S. Brovarets. "Two-stage threecomponent synthesis of 6,11-diaza-1,5(2,5)-dioxazole- 3(1,2)-benzenecycloundecapha ne-14,54- dicarbonitrile." Reports of the National Academy of Sciences of Ukraine, no. 11 (2020): 71–77. http://dx.doi.org/10.15407/dopovidi2020.11.071.

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The possibilities of 2-amino-3,3-dichloroacrylonitrile (ADAN) used for the construction of macrocyclic structures such as cyclophanes with two oxazole fragments are investigated. For this purpose, bifunctional reagents were used in the classic ADAN transformation into 5-amino-4-cyanooxazoles (sequential treatment of ADAN with acyl chloride and a primary or secondary amine). As a result of the reaction of 2,2'‎-(1,2-phenylene)-diacetyl chloride with 2 eq of ADAN, a compound with two acrylonitrile fragments, 2,2' ‎- (1,2-phenylene)bis(N- (2,2-dichloro-1-cyanovinyl)acetamide), was obtained. In this substance, both ADAN residues can interact with amines and form oxazole cycles: for example, the treatment with an excess of dimethylamine produces 2,2'‎ - (1,2-phenylenebis(methylene))bis(5-(dimethylamino)oxazole-4-carbonitrile). The target macrocyclic structure was obtained by the interaction of 2,2'‎ - (1,2-phenylene)bis(N-(2,2-dichloro-1-cyanovinyl)acetamide) with butane-1,4-diamine, as a result the simultaneous forming of both oxazole rings and an aliphatic bridge connected with them was happened. At this stage, it was used a procedure, that is typical of the creation of macrocyclic structures based on polyfunctional reagents, — strong dilution (about 0.04 M). The molecule of the synthesized 6,11-diaza-1,5(2,5)-dioxazole-3(1,2)-benzenecycloundecaphan-14,54-dicarbonitrile has high spatial symmetry, which is confirmed by the presence of only one series of peaks in the 1H and 13C NMR spectra (for example, the butane-1,4-diamine fragment in the aliphatic part of the spectrum looks likes two triplets). The formation of a macrocyclic structure is evidenced by HPLC-MS data, as well as homo- and heteronuclear correlations in the NMR spectra. The proposed procedure for the synthesis of 6,11-diaza-1,5(2,5)-dioxazole-3(1,2)-benzenecycloundecaphan- 14,54-dicarbonitrile is based on the use of simple and inexpensive reagents, and the total yield of the target substance in two stages starting with the 2,2'‎ - (1,2-phenylene)diacetyl chloride, is 51 %.

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13

Alfonso, Ignacio, M. Isabel Burguete, and Santiago V. Luis. "A Hydrogen-Bonding-Modulated Molecular Rotor: Environmental Effect in the Conformational Stability of Peptidomimetic Macrocyclic Cyclophanes." Journal of Organic Chemistry 71, no. 6 (March 2006): 2242–50. http://dx.doi.org/10.1021/jo051974i.

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14

Werz, Daniel B., Felix R. Fischer, Stefan C. Kornmayer, Frank Rominger, and Rolf Gleiter. "Macrocyclic Cyclophanes with Two and Three α,ω-Dichalcogena-1,4-diethynylaryl Units: Syntheses and Structural Properties." Journal of Organic Chemistry 73, no. 20 (October 17, 2008): 8021–29. http://dx.doi.org/10.1021/jo801378p.

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15

Balog, Mirela, Ion Grosu, Gérard Plé, Yvan Ramondenc, Eric Condamine, and Richard A. Varga. "Design and Synthesis of New Macrocyclic Cyclophanes Using 1,3-Dioxane Units as Bridges: A Molecular “Rocking Chair”." Journal of Organic Chemistry 69, no. 4 (February 2004): 1337–45. http://dx.doi.org/10.1021/jo0353987.

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16

Gorbachuk, Vladimir V., Anna R. Marysheva, and Ivan I. Stoykov. "Total oxidation of decahydroxypillar[5]arene with copper(II) and iron(III) nitrates." Butlerov Communications 63, no. 7 (July 31, 2020): 19–23. http://dx.doi.org/10.37952/roi-jbc-01/20-63-7-19.

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Pillar[n]arenes are suitable synthetic platforms for synthesis of functionalized p-cyclophanes, versatile building blocks for creating supramolecular polymers and (pseudo)rotaxanes. The presence of hydroquinone fragments in unsubstituted pillar[n]arene derivatives opens wide opportunities for their application in electrochemical sensors and for their use as reducing agents for synthesis of hybrid materials. Macrocyclic cavity plays the key role in molecular recognition, supramolecular self-assembly of pillararenes, and therefore possibility of switching electron donor properties of aromatic moieties, forming macrocyclic cavity presents specific interest. Synthesis of pillar[n]quinones is non-trivial goal, usually, it requires expensive reagents (сerium(IV) ammonium nitrate). As an oxidized compound alkoxy-derivatives of pillararenes are used. While possibility of red-ox transitions of decahydroxypillar[5]arene are well known, to the date in literature there are no examples of total oxidation of decahydroxypillar[5]arene. We have studied interaction of decahydroxy-pillar[5]arene with a row of inorganic oxidants: catalytic oxidation with air oxygen in presence of copper(II) and iron(III) nitrates, and oxidation with ammonium persulfate. In order to find the optimal conditions for oxidation of pillar[5]arene the series of solvents were tried (proton donor alcohols and acetic acid, proton acceptor dimethylformamide and dimethylsulfoxide). It was established that using glacial acetic acid as a solvent with ultrasonication leads to total oxidation of pillar[5]arene to pillar[5]quinone. This fact is explained by strong proton-donor properties of glacial acetic acid, to prevent formation of insoluble quinhydrone complexes of pillar[5]arene oxidation products. Using ammonium persulfate does not lead to the product of total oxidation.

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17

Wilcox, Craig S., and Marlon D. Cowart. "New approaches to synthetic receptors. Studies on the synthesis and properties of macrocyclic C-glycosyl compounds as chiral, water-soluble cyclophanes." Carbohydrate Research 171, no. 1 (December 1987): 141–60. http://dx.doi.org/10.1016/s0008-6215(00)90884-x.

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18

Yamato, Takehiko, Koji Tsuchihashi, Noriko Nakamura, Mai Hirahara, and Hirohisa Tsuzuki. "Medium-sized cyclophanes, part 59:1 Nitration of [3.3]- and [3.3.3]metacyclophanes Through-space electronic interactions between two or three benzene rings." Canadian Journal of Chemistry 80, no. 2 (February 1, 2002): 207–15. http://dx.doi.org/10.1139/v02-009.

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The two tert-butyl groups of anti-6,15-di-tert-butyl-9,18-dimethoxy[3.3]metacyclophane (anti-4) are both ipso-nitrated even under mild reaction conditions such as copper(II) nitrate in an acetic anhydride solution because of the decreased deactivation of the second aromatic ring by the introduced nitro group. On the other hand, anti-5,13-di-tert-butyl-8,16-dimethoxy[2.2]metacyclophane (anti-1) undergoes replacement of only one tert-butyl group under the same reaction conditions. The higher yields of the twofold ipso-nitration product anti-7 were obtained in nitration of anti-4 with fuming nitric acid or mixed acid (HNO3H2SO4). Thus, the number of ipso-nitrations at the tert-butyl groups of anti-4 was strongly affected by the reactivity of the nitration reagent. Nitration of the corresponding syn-conformer syn-4 with copper(II) nitrate in an acetic anhydride solution, however, led only to the recovery of the starting compound. The presently developed procedure was further applied to the direct removal of the tert-butyl group by electrophilic substitution of the larger-sized ring macrocyclic metacyclophanes, cone- and partial-cone-tri-tert-butyl[3.3.3]metacyclophanes 11.Key words: [3n]metacyclophanes, conformation, ipso-nitration, through-space electronic interaction, crystal structure.

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19

Murakami, Yukito, Junichi Kikuchi, Teruhisa Ohno, Osamu Hayashida, and Masayo Kojima. "Syntheses of macrocyclic enzyme models. 7. Octopus cyclophanes having L-aspartate residues as novel water-soluble hosts; aggregation behavior and induced-fit molecular recognition." Journal of the American Chemical Society 112, no. 21 (October 1990): 7672–81. http://dx.doi.org/10.1021/ja00177a031.

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20

Soberanes, Yedith, Rosa Elena Navarro, Motomichi Inoue, Hisila Santacruz-Ortega, Refugio Pérez-González, Karen Ochoa Lara, and Rogerio R. Sotelo-Mundo. "Interaction of Na+ and K+ ions with DTPA-amide dioxa-pentaaza-cyclophanes: effect of electrostatic field in macrocyclic cavity on UV absorption spectra and protonation." Journal of Inclusion Phenomena and Macrocyclic Chemistry 92, no. 3-4 (November 21, 2018): 419–26. http://dx.doi.org/10.1007/s10847-018-0864-3.

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21

Marsau, Pierre, Gérard Guinand, Jean Hinschberger, Jean-Pierre Desvergne, and Henri Bouas-Laurent. "Molecular and Crystal Structure of a Bisanthracene-9,10-diyl Macrocyclic Coronand AAO5O5 and of its Bis-1,4-endoperoxide, a Bistetraoxapaddlane." Australian Journal of Chemistry 57, no. 11 (2004): 1085. http://dx.doi.org/10.1071/ch04068.

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AAO5O5 3, a bisanthracene macrocyclic cyclophane, is known to be an excimer-type fluorosensor for sodium cations and to encapsulate electron-deficient species such as paraquat. Its bis-1,4-endoperoxide 4 is a tetraoxapaddlane. The molecular and crystal structures of 3 and 4 are described.

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22

Mehta, Goverdhan, Chebiyyam Prabhakar, Munirathinam Nethaji, and Kailasam Venkatesan. "Triquinane-derived macrocyclic cyclophane hosts." Journal of the Chemical Society, Chemical Communications, no. 5 (1993): 483. http://dx.doi.org/10.1039/c39930000483.

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23

HIROTSU, Ken, and Taiichi HIGUCHI. "Structure of macrocyclic cyclophane inclusion compounds." Nihon Kessho Gakkaishi 28, no. 4 (1986): 261–72. http://dx.doi.org/10.5940/jcrsj.28.261.

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24

Podyachev, Sergey N., Rustem R. Zairov, and Asiya R. Mustafina. "1,3-Diketone Calix[4]arene Derivatives—A New Type of Versatile Ligands for Metal Complexes and Nanoparticles." Molecules 26, no. 5 (February 24, 2021): 1214. http://dx.doi.org/10.3390/molecules26051214.

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The present review is aimed at highlighting outlooks for cyclophanic 1,3-diketones as a new type of versatile ligands and building blocks of the nanomaterial for sensing and bioimaging. Thus, the main synthetic routes for achieving the structural diversity of cyclophanic 1,3-diketones are discussed. The structural diversity is demonstrated by variation of both cyclophanic backbones (calix[4]arene, calix[4]resorcinarene and thiacalix[4]arene) and embedding of different substituents onto lower or upper macrocyclic rims. The structural features of the cyclophanic 1,3-diketones are correlated with their ability to form lanthanide complexes exhibiting both lanthanide-centered luminescence and magnetic relaxivity parameters convenient for contrast effect in magnetic resonance imaging (MRI). The revealed structure–property relationships and the applicability of facile one-pot transformation of the complexes to hydrophilic nanoparticles demonstrates the advantages of 1,3-diketone calix[4]arene ligands and their complexes in developing of nanomaterials for sensing and bioimaging.

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25

Yamato, Takehiko, Kenji Kumamaru, and Hirohisa Tsuzuki. "The metal template effect on O-alkylation of tetrahydroxy[3.1.3.1]metacyclophane with 4-(chloromethyl)pyridine to afford tetrakis- [(4-pyridylmethyl)oxy][3.1.3.1]metacyclophanes and their conformational studies." Canadian Journal of Chemistry 79, no. 10 (October 1, 2001): 1422–30. http://dx.doi.org/10.1139/v01-115.

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An attempted O-alkylation of the flexible macrocycle tetrahydroxy[3.1.3.1]metacyclophane (1) with 4-(chloromethyl) pyridine (2a) in the presence of NaH under THF reflux gave 1,3-di-O-substitution product distal-3a as a major product. In contrast, tetraol 1 was O-alkylated with 2a in the presence of Cs2CO3 to afford a mixture of two conformers of tetra-O-alkylated product 4a in a ratio of 77:23 (1,4-alternate-4a:partial-cone-4a) in 95% yield. No formation of the cone conformer in the reaction of the tetraol 1 with 2a, in comparison with those with 2-(chloromethyl) pyridine (2b) or benzyl bromide (2c) in the presence of NaH or K2CO3, which predominantly afforded cone-conformer, might be attributable to the absence of contributions derived from cationN interactions as well as cationπ interactions. The latter effect might be much smaller because of the decreased π-density of the pyridine ring compared to that of the benzene ring. The structural characterization of these products in solution as well as solid state is also discussed.Key words: macrocycles, calixarenes, cyclophanes, [3.1.3.1]metacyclophanes, O-alkylation, conformation, crystal structure, cationN interaction.

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26

Yamato, Takehiko, Mitsuteru Haraguchi, Jun-Ichi Nishikawa, Seiji Ide, and Hirohisa Tsuzuki. "Synthesis, conformational studies, and inclusion properties of tris[(2-pyridylmethyl)oxy]hexahomotrioxacalix[3]arenes." Canadian Journal of Chemistry 76, no. 7 (July 1, 1998): 989–96. http://dx.doi.org/10.1139/v98-102.

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O-Alkylation of the flexible macrocycle 1 with 2-(chloromethyl)pyridine in the presence of Cs2CO3 resulted in the preferential formation of partial-cone-2. The cone-to-partial-cone ratio of 2 increased in the presence of K2CO3, and led to almost equal in the presence of NaH. The template effect of the alkali metal cations plays an important role in this O-alkylation reaction. The structural characterization of these products is also discussed. The two-phase solvent extraction data indicated that tris[(2-pyridylmethyl)oxy]hexahomotrioxacalix[3]arenes 2 show moderate extractability for n-butylammonium ion and high extractability for Ag+. The 1H NMR titration of cone-2 with AgSO3CF3 clearly demonstrates that a 1:1 complex is formed, which is stable on the NMR time scale. Thus, the synergism of cyclophane moiety and two or three lower-rim side chains with pyridyl groups play a significant role on the complexation of tris[(2-pyridylmethyl)oxy] derivatives cone-2 and partial-cone-2 with Ag+ ion and n-butylammonium ion.Key words: macrocycles, calixarenes, O-alkylation, ionophores, cation-N interaction.

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27

Granzhan, Anton, David Monchaud, Nicolas Saettel, Aurore Guédin, Jean-Louis Mergny, and Marie-Paule Teulade-Fichou. "“One Ring to Bind Them All”—Part II: Identification of Promising G-Quadruplex Ligands by Screening of Cyclophane-Type Macrocycles." Journal of Nucleic Acids 2010 (2010): 1–11. http://dx.doi.org/10.4061/2010/460561.

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A collection of 26 polyammonium cyclophane-type macrocycles with a large structural diversity has been screened for G-quadruplex recognition. A two-step selection procedure based on the FRET-melting assay was carried out enabling identification of macrocycles of high affinity (ΔT1/2up to30°C) and high selectivity for the human telomeric G-quadruplex. The four selected hits possess sophisticated architectures, more particularly the presence of a pendant side-arm as well as the existence of a particular topological arrangement appear to be strong determinants of quadruplex binding. These compounds are thus likely to create multiple contacts with the target that may be at the origin of their high selectivity, thereby suggesting that this class of macrocycles offers unique advantages for targeting G-quadruplex-DNA.

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28

Sakamaki, Daisuke, Akihiro Ito, Takashi Matsumoto, and Kazuyoshi Tanaka. "Electronic structure of tetraaza[1.1.1.1]o,p,o,p-cyclophane and its oxidized states." RSC Adv. 4, no. 74 (2014): 39476–83. http://dx.doi.org/10.1039/c4ra06065b.

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29

Kotha, Sambasivarao, Milind Meshram, and Chandravathi Chakkapalli. "Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps." Beilstein Journal of Organic Chemistry 14 (September 21, 2018): 2468–81. http://dx.doi.org/10.3762/bjoc.14.223.

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This account provides an overview of recent work, including our own contribution dealing with Suzuki–Miyaura cross coupling in combination with metathesis (or vice-versa). Several cyclophanes, polycycles, macrocycles, spirocycles, stilbenes, biaryls, and heterocycles have been synthesized by employing a combination of Suzuki cross-coupling and metathesis. Various popular reactions such as Diels–Alder reaction, Claisen rearrangement, cross-metathesis, and cross-enyne metathesis are used. The synergistic combination of these powerful reactions is found to be useful for the construction of complex targets and fulfill synthetic brevity.

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30

Viswanathan, Vijayan, Ayyavu Thirunarayanan, Perumal Rajakumar, and Devadasan Velmurugan. "An amide cyclophane." Acta Crystallographica Section E Structure Reports Online 70, no. 8 (July 11, 2014): o865. http://dx.doi.org/10.1107/s1600536814015621.

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The title compound, 8,18-dithia-2,6-diaza-13(1,4)-piperidina-1(1,2),4(1,3),7(1,2)-tribenzenaoctadecaphane-10,15-diyne-3,6-dione, C32H30N4O2S2, is composed of a relatively planar bis(2-mercaptophenyl)isophthalamide unit linked to a bridging 1,4-di(but-2-yn-1-yl)piperazine unit, forming a macrocycle. The isophthalamide ring is inclined to the outer mercaptophenyl rings by 8.18 (11) and 5.59 (10)°, while these two rings are inclined to one another by 9.10 (12)°. The piperazine ring adopts a chair conformation. There are two intramolecular N—H...S hydrogen bonds generatingS(5) ring motifs. In the crystal, molecules are linkedviaC—H...S and C—H...O hydrogen bonds, forming slabs lying parallel to (001). An O atom in the isophthalamide group is disordered over two positions with an occupancy ratio of 0.41 (6):0.59 (6).

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31

Heerklotz, Jörg A, Changchun Fu, Anthony Linden, and Manfred Hesse. "Photochemical Ring Enlargement of MacrocyclicN-Phenyl Imides into Cyclophanes." Helvetica Chimica Acta 83, no. 8 (August 9, 2000): 1809–24. http://dx.doi.org/10.1002/1522-2675(20000809)83:8<1809::aid-hlca1809>3.0.co;2-l.

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32

Phan, Ngoc-Minh, Emma P. K. L. Choy, Lev N. Zakharov, and Darren W. Johnson. "Self-sorting in dynamic disulfide assembly: new biphenyl-bridged “nanohoops” and unsymmetrical cyclophanes." Chemical Communications 55, no. 79 (2019): 11840–43. http://dx.doi.org/10.1039/c9cc06503b.

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33

Groot, Broer de, Hilary A. Jenkins, Stephen J. Loeb, and Shannon L. Murphy. "Ruthenium(II) complexes of the thiacyclophane ligands 2,5,8-trithia[9]-o-cyclophane (TT[9]OC) and 5-oxa-2,8-dithia[9]-o-cyclophane (ODT[9]OC). Structures of RuCl2(DMSO)(TT[9]OC) and RuCl2(PPh3)(ODT[9]OC)." Canadian Journal of Chemistry 73, no. 7 (July 1, 1995): 1102–10. http://dx.doi.org/10.1139/v95-136.

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Abstract:

Ruthenium(II) complexes of the thiacyclophane ligands 2,5,8-trithia[9]-o-cyclophane (TT[9]OC) and 5-oxa-2,8-dithia[9]-o-cyclophane (ODT[9]OC) were synthesized by ligand displacement reactions employing RuCl2(DMSO)4, RuCl2(PPh3)3, and RuHCl(PPh3)3 as starting materials. X-ray crystal structures of two of these complexes, RuCl2(DMSO)(TT[9]OC) and RuCl2(PPh3)(ODT[9]OC), demonstrate how TT[9]OC and ODT[9]OC bind to Ru(II). RuCl2(DMSO)(TT[9]OC) crystallized as the DMSO solvate in the orthorhombic space group Pbca with a = 19.590(5), b = 16.849(4), c = 13.149(4) Å, V = 4340(3) Å3, and Z = 8. The structure refined to R = 5.27% and Rw = 6.27% for 2472 reflections with Fo2 > 3σ(Fo2). RuCl2(PPh3)(ODT[9]OC) crystallized as a ClCH2CH2Cl solvate in the monoclinic space group P21/c with a = 7.912(1), b = 22.419(5), c = 18.794(3) Å, β = 101.12(1),° V = 3271.2(9) Å3, and Z = 4. The structure refined to R = 4.96% and Rw = 5.14% for 1800 reflections with Fo2 > 3σ(Fo2). Both compounds are octahedral with the thiacyclophane ligand bound through three donor atoms in a facial coordination mode, cis chlorine atoms, and the unique ancillary ligand, DMSO or PPh3, bound trans to the central S or O donor of the macrocycle. The X-ray structures support 1H NMR spectral evidence which shows that the ligands are bound in an "endo" mode for L = DMSO and in an "exo" mode when L = PPh3. The reaction of RuHCl(PPh3)3 with TT[9]OC yields the ruthenium hydride complex RuHCl(PPh3)2(TT[9]OC). 1H and 31P NMR spectroscopy are consistent with an octahedral species for which the macrocycle occupies only two coordination sites acting as a bidentate η2-chelating ligand. Keywords: thioether, macrocycle, hydride, crystal structure.

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34

Kotha, Sambasivarao, and Somnath Halder. "Synthesis of macrocyclic cyclophane-based unusual α-amino acid derivatives." Arkivoc 2005, no. 3 (October 2, 2004): 56–66. http://dx.doi.org/10.3998/ark.5550190.0006.308.

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35

Kihara, Nobuhiro, Kazuhiko Saigo, Yoshio Kabata, Mami Ohno, and Masaki Hasegawa. "Lithium Selective Complexation by a Novel Cyclophane-type Macrocyclic Ligand." Chemistry Letters 18, no. 7 (July 1989): 1289–92. http://dx.doi.org/10.1246/cl.1989.1289.

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36

Nour, Hany F., Agnieszka Golon, and Nikolai Kuhnert. "Synthesis of novel chiral tetra-(hydrazinecarboxamide) cyclophane macrocycles." Tetrahedron Letters 54, no. 32 (August 2013): 4139–42. http://dx.doi.org/10.1016/j.tetlet.2013.05.085.

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37

Kawase, Takeshi. "Allenophane and Allenoacetylenic Macrocycles: A New Class of Chiral Cyclophanes." Angewandte Chemie International Edition 44, no. 45 (November 18, 2005): 7334–36. http://dx.doi.org/10.1002/anie.200502474.

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38

Zeller, Matthias, Marlon R. Lutz Jr, and Daniel P. Becker. "An aza-cyclophane stacked in racemic columnar assemblies: whole-molecule disorder in a two-dimensional solid solution." Acta Crystallographica Section B Structural Science 65, no. 2 (February 20, 2009): 223–29. http://dx.doi.org/10.1107/s0108768109002134.

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The oxime derivative of [1.1.1]cyclophane cyclotriveratrylene (CTV) was ring expanded utilizing a Beckmann rearrangement to provide a ten-membered N-acetyl macrocyclic amide that crystallizes as a chloroform monosolvate in columnar assemblies manifesting an unusual disorder within the crystal. Columns made up of this structure consist of infinite columnar assemblies of alternating D and L enantiomers and therefore necessarily are made up of a racemate, yet the chiralities of individual molecules in adjacent columns are independent of one another, leading to the overall formation of a two-dimensional solid solution. The random arrangement of the columns within the structure leads to the emergence of a crystallographic mirror plane not reflected by the molecular symmetry, to a change of symmetry from Pna21 to Pnma and to whole-molecule disorder of the bowl-shaped molecules within the columns.

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39

Kotha, Sambasivarao, and Mukesh Shirbhate. "Diversity-Oriented Approach to Macrocyclic Cyclophane Derivatives via Ring-Closing Metathesis." Synlett 23, no. 15 (August 31, 2012): 2183–88. http://dx.doi.org/10.1055/s-0032-1317020.

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40

Nour, Hany F., Nadim Hourani, and Nikolai Kuhnert. "Synthesis of novel enantiomerically pure tetra-carbohydrazide cyclophane macrocycles." Organic & Biomolecular Chemistry 10, no. 22 (2012): 4381. http://dx.doi.org/10.1039/c2ob25171j.

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41

Spenst, Peter, and Frank Würthner. "Photo- and redoxfunctional cyclophanes, macrocycles, and catenanes based on aromatic bisimides." Journal of Photochemistry and Photobiology C: Photochemistry Reviews 31 (June 2017): 114–38. http://dx.doi.org/10.1016/j.jphotochemrev.2017.03.002.

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42

Li, Guangwu, Taisuke Matsuno, Yi Han, Hoa Phan, Shaofei Wu, Qing Jiang, Ya Zou, Hiroyuki Isobe, and Jishan Wu. "Benzidine/Quinoidal‐Benzidine‐Linked, Superbenzene‐Based π‐Conjugated Chiral Macrocycles and Cyclophanes." Angewandte Chemie International Edition 59, no. 24 (April 7, 2020): 9727–35. http://dx.doi.org/10.1002/anie.202002447.

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43

Li, Guangwu, Taisuke Matsuno, Yi Han, Hoa Phan, Shaofei Wu, Qing Jiang, Ya Zou, Hiroyuki Isobe, and Jishan Wu. "Benzidine/Quinoidal‐Benzidine‐Linked, Superbenzene‐Based π‐Conjugated Chiral Macrocycles and Cyclophanes." Angewandte Chemie 132, no. 24 (April 7, 2020): 9814–22. http://dx.doi.org/10.1002/ange.202002447.

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44

Yamato, Takehiko, Yuko Kinosaki, and Fenglei Zhang. "ipso-NITRATION OF HEXAMETHOXY[(2.1)3]METACYCLOPHANE, A CALIXARENE ANALOGOUS MACROCYCLIC META CYCLOPHANE." Organic Preparations and Procedures International 31, no. 2 (April 1999): 167–72. http://dx.doi.org/10.1080/00304949909355706.

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45

Hegmann, Torsten, Bernhard Neumann, Jens Kain, Siegmar Diele, and Carsten Tschierske. "Butterfly-mesogens: para-cyclophane based macrocyclic metallomesogens forming smectic and columnar liquid crystalline phases." Journal of Materials Chemistry 10, no. 10 (2000): 2244–48. http://dx.doi.org/10.1039/b003594g.

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46

Iwanaga, Tetsuo, Ryoma Nakamoto, Mikio Yasutake, Hiroyuki Takemura, Katsuya Sako, and Teruo Shinmyozu. "Cyclophanes within Cyclophanes: The Synthesis of a Pyromellitic Diimide-Based Macrocycle as a Structural Unit in a Molecular Tube and Its Inclusion Phenomena." Angewandte Chemie International Edition 45, no. 22 (May 26, 2006): 3643–47. http://dx.doi.org/10.1002/anie.200504499.

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47

Iwanaga, Tetsuo, Ryoma Nakamoto, Mikio Yasutake, Hiroyuki Takemura, Katsuya Sako, and Teruo Shinmyozu. "Cyclophanes within Cyclophanes: The Synthesis of a Pyromellitic Diimide-Based Macrocycle as a Structural Unit in a Molecular Tube and Its Inclusion Phenomena." Angewandte Chemie 118, no. 22 (May 26, 2006): 3725–29. http://dx.doi.org/10.1002/ange.200504499.

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48

Dell, Steven, Douglas M. Ho, and Robert A. Pascal. "Cyclophanes with Sharp Corners: Synthesis of Macrocycles Containing One or Two 1,5,2,4,6,8-Dithiatetrazocine Rings." Inorganic Chemistry 35, no. 10 (January 1996): 2866–71. http://dx.doi.org/10.1021/ic960172q.

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49

Odermatt, Severin, J. Lorenzo Alonso-Gómez, Paul Seiler, M. Magdalena Cid, and François Diederich. "Shape-Persistent Chiral Alleno-Acetylenic Macrocycles and Cyclophanes by Acetylenic Scaffolding with 1,3-Diethynylallenes." Angewandte Chemie International Edition 44, no. 32 (August 12, 2005): 5074–78. http://dx.doi.org/10.1002/anie.200501621.

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Lahoz, Inmaculada R., Armando Navarro-Vázquez, José Lorenzo Alonso-Gómez, and M. Magdalena Cid. "Acetylenic Homocoupling Methodology Towards the Synthesis of 1,3-Butadiynyl Macrocycles: [142]-Alleno-Acetylenic Cyclophanes." European Journal of Organic Chemistry 2014, no. 9 (January 15, 2014): 1915–24. http://dx.doi.org/10.1002/ejoc.201301701.

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