Supramolekulare Gänseblümchenketten durch Selbstorganisation

Ashton, Peter R.; Parsons, Ian W.; Raymo, Françisco M.; Stoddart, J. Fraser; White, Andrew J. P.; Williams, David J.; Wolf, Reinhard

doi:10.1002/(sici)1521-3757(19980703)110:13/14<2016::aid-ange2016>3.0.co;2-4

Cited by 27 publications

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“…1 is named as a [2]catenane, 5 as a [3]catenane, and 6 as an [8]catenane, 2 as a [2]rotaxane, 7, 8 and 9 as [3]rotaxanes.…”

Section: Rules and Examplesmentioning

confidence: 99%

“…Thus, they are not suggestive of the total structure or at least of a "cartoon" of the molecule only by flying over the name, and it takes more time to recognize the linking pattern or to draw a graph [2b]. Experience shows, however, that such nomenclatures are only adopted and frequent- 4 Hence, it is easy to understand that new mechanically linked molecular architectures have been given trivial names for years, as illustrated by the expressions "catenanes", "rotaxanes", "knotanes" [6], "pretzelanes" [7], "daisy rotaxanes" [8], "catrotanes" [9a], "rotacatenanes" [9b], "bonnanes" [10]. Without further rules and a hierarchy of rules it will be even more difficult to name more complicated catenanes and rotaxanes like 4, built up from several rings and assemblies of covalently and mechanically linked units [11].…”

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Nomenclature for Catenanes, Rotaxanes, Molecular Knots, and Assemblies Derived from These Structural Elements

et al. 2000

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The IUPAC notation system does not provide a nomenclature for interlocked, mechanically linked molecules beyond very simple catenanes and rotaxanes [1]. Whereas simple catenanes and rotaxanes like 1 and 2 can be named explicitly as [2]catenane and [2]rotaxane according to IUPAC, [1] one already brakes new ground with the naming of additionally bridged types of compounds -such as "pretzelanes" 3 [2] which are easily accessible nowadays.Abstract. We introduce a systematic nomenclature for mechanically linked molecules -such as catenanes, rotaxanes, and assemblies derived from these structural elements -which comes up to the increasing complexity of already synthesized interlocked molecules and the ones to be expected in future. Like in the naming of other substance classes (polycycles, ly used by chemists, if they are constructed from easily comprehensible characteristic parts, basing on immediately convincing rules. Like in the former cases mentioned above a new nomenclature seems to be sensible, which contains -analogously to the bicyclo nomenclature of von Baeyer and to the crown compounds, cyclophanes [3], podands [4], and dendrimers [5] -a characteristic part of the name, for example in brackets, so that it indicates the "overall structure" and its most important features, such as e.g. the type, number, and sequence of the mechanical bonds particularly relevant in this case. phanes, crown compounds, podands, dendrimers) we attach importance to the fact, that certain units in the name, e.g. expressions in brackets, quickly convey an idea of the molecular architecture. Furthermore, this modular nomenclature reveals as many analogies to the IUPAC nomenclature as possible.

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“…1 is named as a [2]catenane, 5 as a [3]catenane, and 6 as an [8]catenane, 2 as a [2]rotaxane, 7, 8 and 9 as [3]rotaxanes.…”

Section: Rules and Examplesmentioning

confidence: 99%

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confidence: 99%

Nomenclature for Catenanes, Rotaxanes, Molecular Knots, and Assemblies Derived from These Structural Elements

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Highly Stable Self-Association of 5-(Guanidiniocarbonyl)-1H-pyrrole-2-carboxylate in DMSO – The Importance of Electrostatic Interactions

Schmuck

1999

Eur. J. Org. Chem.

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The zwitterionic compound 5‐(guanidiniocarbonyl)‐1H‐pyrrole‐2‐carboxylate (1) self‐assembles to form dimers, which are completely stable in DMSO even at 170 °C or at concentrations of 0.001 mM. This high stability stems from a combination of multiple weak interactions. NMR titrations of 1H‐pyrrole‐2‐carboxylate (5) with (1H‐pyrrole‐2‐carbonyl)guanidinium (6) and [5‐(methoxycarbonyl)‐1H‐pyrrole‐2‐carbonyl]guanidinium (8) led to binding constants of K ≈ 106 mol–1 in DMSO and K ≈ 103 mol–1 in 40% water/DMSO for carboxylate binding by the 2‐(guanidiniocarbonyl)pyrrole moiety. The stability constant for the dimer 12 in DMSO could therefore be estimated as K ≈ 1012 mol–1. In solution, the self‐association process of 1 can be completely disrupted by protonation of the carboxylate group. In the solid state, however, the hydrochloride salt 1+ also exists as a similar but only very weakly hydrogen‐bonded dimer.

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A Self-Complexing [2]Catenane

et al. 2000

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Molecules capable of recognizing one or more identical copies of themselves can be employed for the noncovalent synthesis [1] of supermolecules and/or supramolecular arrays. Indeed, self-replicating systems, [2] self-assembling capsules, [3] and supramolecular polymers [4, 5] have all been developed successfully by employing appropriate self-complementary molecules as precursors. Consequently, we contemplated the possibility of synthesizing receptor molecules incorporating mechanically interlocked [6] components by modifying the design of some [2]catenanes [7] such that they acquire receptor characteristics. These [2]catenanes incorporate a 1,5-dioxynaphthalene-based macrocyclic polyether component interlocked with cyclobis(paraquat-4,4'-biphenylene) [8] and are able to bind [7] p-electron-deficient and p-electron-rich substrates. These recognition phenomena have already been exploited in the synthesis of a ªrotacatenaneº [7b] composed of a 1,5-dioxynaphtho[38]crown-10 moiety interlocked with cyclobis(paraquat-4,4'-biphenylene) [8] and with a third acyclic polyether component containing a 1,5-dioxynaphthalene ring system threaded through the cavity of the bipyridinium-based cyclophane and stoppered by bulky groups.To generate self-complementary [2]catenanes, we have lengthened and introduced some flexibility into the spacers separating the bipyridinium units in the tetracationic cyclophane component. By inserting a 2,6-bis(oxymethyl)pyridine unit between the two phenylene rings of the 4,4'-bitolyl spacers, the size of the cavity associated with cyclobis(paraquat-4,4'-biphenylene) can be enlarged and enriched with hydrogen bonding acceptorsÐnamely, the nitrogen and oxygen atoms of the 2,6-bis(oxymethyl)pyridine unit. Here, we report the template-directed synthesis of a self-complementary [2]catenane and the formation of a supramolecular homodimer composed of two mutually interpenetrating [2]catenanes both in solution and in the solid state.Reaction of 1´2 PF 6 and 2 [9] in the presence of the 1,5dioxynaphthalene-based macrocyclic polyether 3 gives the [2]catenane 4´4 PF 6 in 18 % yield after counterion exchange (Scheme 1), together with small amounts of a [3]catenane incorporating one tetracationic cyclophane and two macrocyclic polyether components. Scheme 1. The template-directed synthesis of the [2]catenane 4´4 PF 6 .

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Supramolekulare Gänseblümchenketten durch Selbstorganisation

Cited by 27 publications

References 29 publications

Nomenclature for Catenanes, Rotaxanes, Molecular Knots, and Assemblies Derived from These Structural Elements

Nomenclature for Catenanes, Rotaxanes, Molecular Knots, and Assemblies Derived from These Structural Elements

Highly Stable Self-Association of 5-(Guanidiniocarbonyl)-1H-pyrrole-2-carboxylate in DMSO – The Importance of Electrostatic Interactions

A Self-Complexing [2]Catenane

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