Six-nitrogen macrocyclic complexes of the dioxouranium(VI) and praseodymium(III) ions

Benetollo, Franco; Bombieri, G.; Cola, Luisa De; Polo, A.; Smailes, D. L.; Vallarino, L. M.

doi:10.1021/ic00317a011

Cited by 24 publications

(12 citation statements)

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“…Theoretical calculations on related Schiff base macrocycles,39 as well as single‐crystal XRD data from dodecahydrohexaazakekulene derivatives11 and bis(1,10‐phenanthrolinyl‐2,5‐pyrrole),40 revealed that the distance between two opposite nitrogen atoms of the hexagonal cavity was between 5.0 and 6.0 Å for these compounds; this is in good agreement with our results. Therefore, it can be anticipated that only large alkaline,3–5, 8, 11 alkaline earth,5, 10 and transition‐metal cations3, 6 will be suitable guests for 7 a – c .…”

Section: Resultsmentioning

confidence: 99%

“…However, significant deviations from planarity will be encountered and prevent efficient face‐to‐face packing of these molecules in the solid state 5. 6 On the contrary, cyclosexipyridine D 7, 8 is a hexaaza macrocycle, in which the aromatic units are connected through aryl–aryl bonds with the six nitrogen atoms directed towards the center of the cavity. Additional fusion of the six pyridine units of D through ethyl linkages will further increase both rigidity and planarity 9–12.…”

Section: Introductionmentioning

confidence: 99%

“…[1,2] Examples of toroidal macrocycles involveanumber of conjugated cyclic Schiff bases derived from the parent hexa [18]azaannulene system A. [1,[3][4][5][6] Depending on the choice of the precursors, pyridine [3][4][5][6] B or 1,10-phenanthroline C [1] contribute to the sixfold binding geometry of these cyclic ligands, which are typicallys ynthesized through [2 + 2] template-assisted cyclocondensation. However,s ignificant deviations from planarity will be encountered and prevent efficient face-to-face packing of these molecules in the solid state.…”

Section: Introductionmentioning

confidence: 99%

“…However,s ignificant deviations from planarity will be encountered and prevent efficient face-to-face packing of these molecules in the solid state. [5,6] On the contrary,c yclosexipyridine D [7,8] is ah exaaza macrocycle, in which the aromatic units are connected through aryl-aryl bonds with the six nitrogen atoms directed towards the center of the cavity. Additional fusion of the six pyridine Scheme1.The molecular structures of representative hexaaza macrocycles with an 18-membered cavity:S chiff base macrocycles A-C,c yclosexipyridine D,d odecahydrohexaazakekulene E,a nd target compoundcyclo-2,9-tris-1,10phenanthroline F. units of D through ethyl linkages will further increase both rigidity and planarity.…”

Section: Introductionmentioning

confidence: 99%

“…[31][32][33] Previous investigations into metal complexation of related toroidal macrocycles, such as cyclosexipyridine D [7,8] and dodecahydrohexaazakekulene E, [9][10][11][12] have been hampered by their poor solubility,i nc ombination with the high polarity of the hexaaza cavity. [7][8][9][10][11][12] Regarding self-assembly,u nderstanding of this class of ligandsh as so far been limited to the crystalline state [3,5,6,11] andt hin films. [12] Liquid crystallinity,w hich can be anticipated from their flat doughnut-like geometry;s urface-assisted 2D self-assembly;a nd the impact of metal guests on the supramolecular chemistry remaini mportant issues yet to be explored.…”

Section: Introductionmentioning

confidence: 99%

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Torands Revisited: Metal Sequestration and Self‐Assembly of Cyclo‐2,9‐tris‐1,10‐phenanthroline Hexaaza Macrocycles

Schwab

Takase

Mavrinsky

et al. 2015

Chemistry A European J

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A series of novel toroidal cyclo-2,9-tris-1,10-phenanthroline macrocycles with an unusual hexaaza cavity are reported. Nickel-mediated Yamamoto aryl-aryl coupling was found to be a versatile tool for the cyclotrimerization of functionalized 1,10-phenathroline precursors. Due to the now improved processability, both liquid-crystalline behavior in the bulk phase and two-dimensional self-assembly at the molecular level could be studied, for the first time, for a torand system. The macrocycles exhibited a strong affinity for the complexation of different metal cations, as evidenced by MALDI-TOF analysis and spectroscopic methods. Experimental results were correlated to an extensive computational study of the cyclo-2,9-tris-1,10-phenanthroline cavity and its binding mode for metal cations. Due to the combination of several interesting features, toroidal macrocycles may find future applications in the field of ion and charge transport through molecular channels, as well as for chemical sensing and molecular writing in surface-confined monolayers under STM conditions.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Torands Revisited: Metal Sequestration and Self‐Assembly of Cyclo‐2,9‐tris‐1,10‐phenanthroline Hexaaza Macrocycles

Schwab

Takase

Mavrinsky

et al. 2015

Chemistry A European J

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Template synthesis of macrocyclic systems based on di‐ and polyamines and polyfunctional dicarbonyl compounds

Gérbéléu

Arion

Burgess

1999

Template Synthesis of Macrocyclic Compounds

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Smart Macrocyclic Molecules: Induced Fit and Ultrafast Self‐Sorting Inclusion Behavior through Dynamic Covalent Chemistry

Han¹,

Pan²,

Lei³

et al. 2010

Chemistry A European J

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A family of macrocycles with oligo(ethylene glycol) chains, 4O, 5O, and 6O, was developed to construct a series of new incorporated macrocycles through dynamic covalent chemistry. These flexible macrocycles exhibited excellent "self-sorting" abilities with diamine compounds, which depended on the "induced-fit" rule. For instance, the host macrocycles underwent conformational modulation to accommodate the diamine guests, affording [1+1] intramolecular addition compounds regardless of the flexibility of the diamine. These macrocycles folded themselves to fit various diamines with different chain length through modulation of the flexible polyether chain, and afforded intramolecular condensation products. However, if the chain of the diamine was too long and rigid, oligomers or polymers were obtained from the mixture of the macromolecule and the diamine. All results demonstrated that inclusion compounds involving conformationally suitable aromatic diamines were thermodynamically favorable candidates in the mixture due to the restriction of the macrocycle size. Furthermore, kinetic and thermodynamic studies of self-sorting behaviors of both mixed 4O-5O and 4O-6O systems were investigated in detail. Finally, theoretical calculations were also employed to further understand such self-sorting behavior, and indicated that the large enthalpy change of H(2)NArArNH(2)@4O is the driving force for the sorting behavior. Our system may provide a model to further understand the principle of biomolecules with high specificity due only to their conformational self-adjusting ability.

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Six-nitrogen macrocyclic complexes of the dioxouranium(VI) and praseodymium(III) ions

Cited by 24 publications

References 0 publications

Torands Revisited: Metal Sequestration and Self‐Assembly of Cyclo‐2,9‐tris‐1,10‐phenanthroline Hexaaza Macrocycles

Torands Revisited: Metal Sequestration and Self‐Assembly of Cyclo‐2,9‐tris‐1,10‐phenanthroline Hexaaza Macrocycles

Template synthesis of macrocyclic systems based on di‐ and polyamines and polyfunctional dicarbonyl compounds

Smart Macrocyclic Molecules: Induced Fit and Ultrafast Self‐Sorting Inclusion Behavior through Dynamic Covalent Chemistry

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