Mechanisch verkn�pfte Molek�le Catenane und Rotaxane

Schill, Gottfried; Zürcher, Clemens

doi:10.1007/bf00620800

Cited by 26 publications

(13 citation statements)

References 26 publications

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“…H NMR: δ ϭ 7.87 (broad s, 4 H, H α ), 7.60 (half of AAЈXXЈ, 8 H, H γ -2,-6), 7.33, 7.26 (AAЈXXЈ with underlying broad signals, 32 H, H β , H δ ), 6.92 (half of AAЈXXЈ, 8 H, H γ -3,-5), 4.31 (q, J ϭ 7.1 Hz, 4 H, CO 2 CH 2 ), 4.05 (t, J ϭ 6.2 Hz, 8 H, ArOCH 2 ), 2.37 (t, J ϭ 7.0 Hz, 8 H, CH 2 CϵC), 1.80 (m, 8 H, OCH 2 CH 2 ), 1.6Ϫ1.2 (m, 70 H, CH 2 , CH3 ) 13. C NMR: δ ϭ 165.3 (CO 2 ), 159.3 (C γ -4), 147.4 (CO 3 ), 147.2 (C α -4), 135.5 (C α -3,-5, C β -1), 133.2 (C γ -2,-6), 132.2 (CH δ ), 131.6 (C α -2,-6, C β -3,-5), 131.5 (CH δ ), 129.2 (C α -1), 128.6 (very broad, C β -2,-6), 125.1 (C δ -1 or C δ -4), 123.2 (C β -4), 120.6 (C δ -1 or C δ -4), 115.4 (C γ -1), 114.9 (C γ -3,-5), 93.6 (CH 2 CϵC), 90.8 (CϵCAr γ ), 88.5 (Ar β CϵC), 81.9 (CϵCϪCϵC), 80.2 (CH 2 CϵC), 75.1 (CϵCϪCϵC), 67.9 (ArOCH 2 ), 61.2 (CO 2 CH 2 ), 29.2Ϫ28.7 (7 signals), 25.7, 19.5 (CH 2 ), 14.3 (CH 3 ).…”

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confidence: 99%

The Effect of Ring Size on Catenane Synthesis

Duda

Godt

2003

Eur J Org Chem

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The synthesis of a [2]catenane with 87‐membered rings was improved and extended to [2]catenanes with 63‐ and 147‐membered rings. One of the key features is the carbonate linkage between phenols with tolane substituents in the 2‐ and 6‐positions, which serves as a covalent template for the geometrical arrangement of a macrocycle and a ring precursor. Subsequent cyclization of the threaded ring precursor gives the precatenane as the main product, and this is converted into the catenane by carbonate hydrolysis. As well as the precatenane, its dumbbell shaped isomer is formed in the cyclization step. From the known conformation of the templating carbonate moiety and the strong dependence of the ratio of precatenane and dumbbell on the ring size, the dumbbell's origin is attributed to the conformational flexibility of the large rings and not to geometrical ambiguity of the carbonate moiety. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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confidence: 99%

The Effect of Ring Size on Catenane Synthesis

Duda

Godt

2003

Eur J Org Chem

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“…A different threading scheme could have been expected where a single axle would be threaded through both rings of the same bismacrocycle. This would have led to a doubly charged [2]rotaxane consisting of one dumbbell and one bis-macrocycle (1:1 species). The 1:1 species would have had the same m/z value as the 2:2 species, but the isotope profile would have been different.…”

Section: Resultsmentioning

confidence: 99%

“…The gap between two signals in the isotope profile would have been twice as large. We can thus rule out the possibility that a [2]rotaxane was formed in the reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Porphyrin-containing catenanes and rotaxanes [1] represent an important class of such molecules, [2] either in relation to molecular machines, [3] a particularly active area of research, or as far as electron or energy-transfer processes are concerned. [4] Free-base porphyrins and variously metalated porphyrins (mostly Zn-complexed systems) are important building blocks in the elaboration of multi-component molecules or assemblies able to undergo photoinduced electron and energy transfer processes.…”

Section: Introductionmentioning

confidence: 99%

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A Flexible Copper(I)‐Complexed [4]Rotaxane Containing Two Face‐to‐Face Porphyrinic Plates that Behaves as a Distensible Receptor

Roche

Sour

Sauvage

2012

Chemistry A European J

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A new cyclic [4]rotaxane composed of two flexible bis-macrocycles and two rigid axles is described. Each bis-macrocycle consists of two rings attached to antipodal meso positions of a central Zn porphyrin through single C-C bonds. Each ring incorporates a 2,9-diphenyl-1,10-phenanthroline chelation site. The axles contain two coplanar bidentate sites derived from the 2,2'-bipyridine motif. The building blocks were assembled by using a one-pot threading-and-stoppering reaction, which afforded the [4]rotaxane in 50% yield. The "gathering-and-threading" effect of copper(I) was utilised in the formation of a [4]pseudorotaxane, which was immediately converted to the corresponding [4]rotaxane by a quadruple CuAAC stoppering reaction. The rotaxane contains two face-to-face zinc porphyrins, which allowed the coordination of ditopic guest substrates. The rotaxane host showed remarkable flexibility and was able to adjust its conformation to the guest size. It can be distended and accommodate rod-like guests of 2.6 to 15.8 Å in length.

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“…Yet,catenoid deoxyribonucleic acids in the mitochondria of several cells (catenanes are topologically-mechanically-interlocked molecular architectures, consisting of two or more interlocked macrocycles), are pervasive to organic chemistry and DNA (Schill and Zurcher, 1971).…”

Section: Non-orientable Self-referentialmentioning

confidence: 99%

Surmounting the Cartesian Cut: Klein Bottle Logophysics, The Dirac Algebra and the Genetic Code

Rapoport¹

2011

Neuroquantology

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We reintroduce the Klein Bottle (KB) logophysics at the foundations of the unification of quantum geometry, cell biology, embryology and evolution, to extend it to the genetic code and allosteric recognition. We find that the genetic code has three possible fractal topologies: two different families of KBs embedded in HyperKBs, or still a 2-torus, depending which pair of three subalphabets for the genetic "letters" is chosen; this does not require the double helix. We complete the genetic codification of embryological differentiation introduced in an accompanying article. We discuss the Hadamard-KB representation of this codification and discuss its robustness and that of embryological development with respect to environmental noise. We discuss this KB codification of the 64 codons with its isomorphic representation in terms of the Dirac Algebra (DA) of Quantum Mechanics, in the Nilpotent Universal Computational Rewrite System (NUCRS), a self-referential syntax that generates much of mathematics and the fundamental symmetries of physics. We show that the double helix can be obtained from the duplication of the KB associated with the bistable perception of the tetrahedron representation of the four genetic letters. The DA and its double tetrahedron codification in NUCRS is found to be associated with a pair of superposed KBs, yielding the double 3D (space and momentum) space of physics, and the double helix of DNA, which thus appears related to a pair of KBs, being the case that only one is necessary to construct the genome. We show that the depth-time variable of visual perception materializes as space Thus, the DA is derivable from two KBs, and the purported dualism of physics as presented in NUCRS, is rendered to be based in the non-dualistic KBL. We discuss the relations with a theory of evolutions, and between biological periodicities and the KB of the Mendeleev table (Boeyens). We present relations between metacognition and the HyperKlein Bottle, and evolution in terms of time waves defining in toto the different structures. We present rudiments of the ontoepistemology of the Hyper KB Logic, its relations with the anthropic principles and the universal physical constants, which are found to be contextual.

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Mechanisch verkn�pfte Molek�le Catenane und Rotaxane

Cited by 26 publications

References 26 publications

The Effect of Ring Size on Catenane Synthesis

The Effect of Ring Size on Catenane Synthesis

A Flexible Copper(I)‐Complexed [4]Rotaxane Containing Two Face‐to‐Face Porphyrinic Plates that Behaves as a Distensible Receptor

Surmounting the Cartesian Cut: Klein Bottle Logophysics, The Dirac Algebra and the Genetic Code

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