Synthesis of Macrobicyclic Polyamines by Direct Macrobicyclisation <i>via</i> Tripode‐Tripode Coupling

Dietrich, B.; Hosseini, Mir Wais; Lehn, Jean‐Maríe; Sessions, Richard B.

doi:10.1002/hlca.19850680202

Cited by 77 publications

(25 citation statements)

References 41 publications

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“…[13] The new polyamine macrobicyclic compound was prepared as outlined in Scheme 4. A key element in this synthesis was the 4-(diethoxymethyl)benzaldehyde, in which one of the aldehyde groups is protected in the form of diethylacetal and the other is available to react with tren.…”

Section: Resultsmentioning

confidence: 99%

Recognition of Oxalate by a Copper(II) Polyaza Macrobicyclic Complex

Mateus

Delgado

Brandão

et al. 2011

Chemistry A European J

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A new polyamine macrobicyclic compound was synthesised through a [1+1] "tripod-tripod coupling" strategy and using a Schiff base condensation reaction, followed by sodium borohydride reduction. The resulting compound is a heteroditopic cage (btpN(7)) in which one of the head units is appropriate for the coordination of copper(II), whereas the other head is available for additional hydrogen-bonding and electrostatic interactions with substrates. The acid-base behaviour of the new compound, the stability constants of its complex with the Cu(2+) ion and the association constants of the copper(II) cryptate with oxalate (oxa(2-)), malonate (mal(2-)), succinate (suc(2-)), maleate (male(2-)) and fumarate (fum(2-)) were determined by potentiometry at 298.2 K in aqueous solution and at an ionic strength of 0.10 mol dm(-3) in KNO(3). These studies revealed a clear preference of the receptor [CuH(h)btpN(7)H(2)O]((2+h)+) for oxa(2-) over the other dicarboxylate substrates. This arises from co-operativity between metal-anion coordination and electrostatic and hydrogen-bonding interactions, in accordance with the ideal size of this dicarboxylate, which allow it to take full advantage of the potential binding sites of the receptor. A qualitative indicator-displacement study, in agreement with the potentiometric studies, demonstrated that the copper cryptate receptor can be used as a selective visual sensor for oxalate.

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Section: Resultsmentioning

confidence: 99%

Recognition of Oxalate by a Copper(II) Polyaza Macrobicyclic Complex

Mateus

Delgado

Brandão

et al. 2011

Chemistry A European J

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“…[10a] 2-[2-(2-chloroethoxy)ethoxy]tetrahydropyran (7), [24] 2-[2-(carbazol-9-yl)ethoxy]ethanol (19), [15] 4-(dimethylamino)pyridinium ptoluenesulfonate (DPTS), [25] 2-{2-[2-(2-benzylethoxy)ethoxy]ethoxy}-ptoluene sulfonate (9) [13] and 3,5-(dipyrrolidine-1-yl)phenol (4) [11] were synthesized according to literature procedures. The synthesis of {2-[2-(carbazol-9-yl)ethoxy]ethyl}3,4,5-tris- (12,12,12,11,11,10,10,9,9,8,8,7,7,6,6, 5,5-heptadecafluoro- 4,5-tris(12,12,12,11,11, 10,10,9,9,8,8,7-,7,6,6,5,5-heptadecafluoro-…”

Section: Methodsmentioning

confidence: 99%

Self‐Assembly of Semifluorinated Dendrons Attached to Electron‐Donor Groups Mediates Their π‐Stacking via a Helical Pyramidal Column

Percéc

Glodde

Peterca

et al. 2006

Chemistry A European J

125

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Semifluorinated first-generation self-assembling dendrons attached via a flexible spacer to electron-donor molecules induce pi-stacking of the donors in the center of a supramolecular helical pyramidal column. These helical pyramidal columns self-organize in various columnar liquid crystal phases that mediate self-processing of large single crystal liquid crystal domains of columns and self-repair their intracolumnar structural defects. In addition, all supramolecular columns exhibit a columnar phase at lower temperatures that maintains the helical pyramidal columnar supramolecular structure and displays higher intracolumnar order than that in the liquid crystals phases. The results described here demonstrate the universality of this concept, the power of the fluorous phase or the fluorophobic effect in self-assembly and the unexpected generality of pyramidal liquid crystals.

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“…Commercial grade chemicals were used without further purification, and thionyl chloride from triphenyl phosphite. Benzo-15-crown-5 [18], N-tosylaziridine [19], benzo-15-crown-5-monoaza [20] [20] were prepared according to literature procedures. The alkali picrate extractions were carried out as described in the literature [6,7,24].…”

Section: Experimental Synthesismentioning

confidence: 99%

Synthesis and Properties of Copper(II) Phthalocyanines with Monoazacrown and Crown Ethers as Peripheral Substituents

Kandaz

Bekâroĝlu

1999

J. Porphyrins Phthalocyanines

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Soluble and less soluble phthalocyaninatocopper(II) derivatives (4a and 4b) were prepared from the corresponding 7-[(4′-benzo-15-crown-5)oyl]-15, 16-dibromo-2,3,6,7,8,9,11,12-octahydro-5H-benzo[e]-[1,4,10,13,7] tetraoxaazacyclopentadecine (3a) and 7-(2′-tosylaminoethyl)-15, 16-dibromo-2,3,6,7,8,9,11, 12-octahydro-5H-benzo[e]-[1,4,10,13,7] tetraoxaazacyclopentadecine (3b) and CuCN in pyridine. A less soluble novel multifunctionalized scorpiand macrocycle-substituted phthalocyanine (4c) in which an NH 2 CH 2 CH 2— chain is appended to a monoazacrown ether ring was obtained by detosylation of 4b with concentrated sulfuric acid.

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Synthesis of Macrobicyclic Polyamines by Direct Macrobicyclisation via Tripode‐Tripode Coupling

Cited by 77 publications

References 41 publications

Recognition of Oxalate by a Copper(II) Polyaza Macrobicyclic Complex

Recognition of Oxalate by a Copper(II) Polyaza Macrobicyclic Complex

Self‐Assembly of Semifluorinated Dendrons Attached to Electron‐Donor Groups Mediates Their π‐Stacking via a Helical Pyramidal Column

Synthesis and Properties of Copper(II) Phthalocyanines with Monoazacrown and Crown Ethers as Peripheral Substituents

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