Self‐Assembly of Dinuclear Double‐ and Triple‐Stranded Helicates from Bis(bipyridine) Ligands Derived from Tröger's Base Analogues

Kiehne, Ulf; Weilandt, Torsten; Lützen, Arne

doi:10.1002/ejoc.200701215

Cited by 49 publications

(27 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…2þ on the basis of ROESY NMR experiments and energies of PM3-optimized diastereoisomers but was not unambiguously confirmed [76].…”

Section: Synthesis Of Linear Tris-trçgers Base 29mentioning

confidence: 92%

“…In a reaction between (AE)-37 and a Rh I complex with preferred square planar geometry, a more complicated behavior was observed, namely, the formation of a mixture of di-and trimeric metallomacrocycles [75]. Another class of conceptually new ligands for the metal-mediated self-assembly comprise the Trçgers base scaffold expanded with 2,2'-bipyridine fragments [24] [76]. Upon the coordination of two bis(bipyridine) ligands (AE)-40 around Ag þ cations, selfassembly of a double-stranded helical complex [Ag 2 (40) 2 ] 2þ was observed, as confirmed by ESI-MS. Interestingly, the use of racemic rather than enantiomerically pure ligands allows one to take more advantage of the chirality of the Trçgers base core and gain deeper insight into the self-assembly process.…”

Section: Synthesis Of Linear Tris-trçgers Base 29mentioning

confidence: 98%

See 1 more Smart Citation

Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

Sergeyev

2009

Helvetica Chimica Acta

132

View full text Add to dashboard Cite

Trçgers base is a well-known chiral molecule with a few unusual structural features. The chemistry of Trçgers base analogues has been greatly developed over the last 20 years, and numerous interesting applications in supramolecular chemistry and in molecular recognition have emerged. This Review gives a short overview of the chemistry of Trçgers base and its analogues, with particular focus on recent achievements in synthesis, enantiomer separations, and applications.

show abstract

“…2þ on the basis of ROESY NMR experiments and energies of PM3-optimized diastereoisomers but was not unambiguously confirmed [76].…”

Section: Synthesis Of Linear Tris-trçgers Base 29mentioning

confidence: 92%

Section: Synthesis Of Linear Tris-trçgers Base 29mentioning

confidence: 98%

Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

Sergeyev

2009

Helvetica Chimica Acta

132

View full text Add to dashboard Cite

show abstract

“…[88][89][90][91] The required compound was a 2,2 0 -bipyridine carrying either a halide or an alkynyl substituent in the 5-position. Our first approach started from a published Stille coupling procedure to give 5-nitro-2,2 0 -bipyridine (43) from commercially available 2-chloro-5-nitropyridine (41) and 42, followed by reduction to the amine and Sandmeyer reaction to give the required 5-iodo-2,2 0 -bipyridine.…”

Section: General Considerationsmentioning

confidence: 99%

Versatile tools in the construction of substituted 2,2′-bipyridines—cross-coupling reactions with tin, zinc and boron compounds

2008

Self Cite

View full text Add to dashboard Cite

2,2'-Bipyridines are among the most widely used classes of chelating ligands that have found applications in the fields of coordination chemistry, supra-, nano- and macromolecular chemistry, analytical and photochemistry, but also in asymmetric synthesis and natural product chemistry. Hence, there is a huge demand for efficient synthetic approaches to functionalized derivatives. Modern cross-coupling procedures have been proven to be particularly effective in this context. This critical review will give an overview about the advances made so far focussing mainly on cross-coupling reactions with tin, zinc and boron compounds for the achievement of interesting, versatile and unusual substitution patterns (156 references).

show abstract

“…This product was subjected to chromatography on silica gel and isolated as its PF 6 -salt. The deep red colouration is characteristic of the presence of a low-spin [Fe(bipyridine) 3 ] 2+ chromophore.…”

Section: Expanded Quaterpyridine Ligand Synthesismentioning

confidence: 99%

Nickel(ii) and iron(ii) triple helicates assembled from expanded quaterpyridines incorporating flexible linkages

et al. 2011

View full text Add to dashboard Cite

In the present study the interaction of Fe(II) and Ni(II) with the related expanded quaterpyridines, 1,2-, 1,3-and 1,4-bis-(5¢-methyl-[2,2¢]bipyridinyl-5-ylmethoxy)benzene ligands (4-6 respectively), incorporating flexible, bis-aryl/methylene ether linkages in the bridges between the dipyridyl domains, was shown to predominantly result in the assembly of [M 2 L 3 ] 4+ complexes; although with 4 and 6 there was also evidence for the (minor) formation of the corresponding [M 4 L 6 ] 8+ species. Overall, this result contrasts with the behaviour of the essentially rigid 'parent' quaterpyridine 1 for which only tetrahedral [M 4 L 6 ] 8+ cage species were observed when reacted with various Fe(II) salts. It also contrasts with that observed for 2 and 3 incorporating essentially rigid substituted phenylene and biphenylene bridges between the dipyridyl domains where reaction with Fe(II) and Ni(II) yielded both [M 2 L 3 ] 4+ and [M 4 L 6 ] 8+ complex types, but in this case it was the latter species that was assigned as the thermodynamically favoured product type. The X-ray structures of the triple helicate complexes [

show abstract

Self‐Assembly of Dinuclear Double‐ and Triple‐Stranded Helicates from Bis(bipyridine) Ligands Derived from Tröger's Base Analogues

Cited by 49 publications

References 45 publications

Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

Versatile tools in the construction of substituted 2,2′-bipyridines—cross-coupling reactions with tin, zinc and boron compounds

Nickel(ii) and iron(ii) triple helicates assembled from expanded quaterpyridines incorporating flexible linkages

Contact Info

Product

Resources

About