Bipyridne Building Blocks for Self-Organization Systems: First Complete NMR-spectroscopic Investigation of 6,6'-Disubstituted 2,2'-Bipyridines Obtained via N-Oxidation Route and Related Reactions

Supramolecular self-assembly on a solid support: metal-directed complementarity

“…This was characterised using magic angle spinning nano-probe 1 H NMR which revealed the expected B aromatic signals (d 7.27 (7.17), 7.22 (7.41), 7.57 (7.69), 7.73 (7.79), 8.14 (8.18), 8.35 (8.32) ppm, 6-hydroxymethyl-69-methyl-2,29-bipyridine in CD 3 OD solution in parentheses). 11 Reaction of the functionalised resin 2 with Cu(OTf) 2 (OTf 5 O 3 SCF 3 ) and terpy followed by repeated washing, resulted in the formation of olive green beads, consistent with known {Cu(bipy)(terpy)} 2+ solution species. 8 Treatment of the beads with KCN resulted in decolorisation and a solution phase that contained terpy as the only organic species (Scheme 1).…”

“…which was then reacted with 1 and BF 3 ?Et 2 O to give the B-functionalised resin 3. Deprotonation (NaH-DMF) followed by reaction with 6-bromomethyl-69-methyl-2,29-bipyridine 11 yielded the resin functionalised with a bis-bipy BNB strand 4 (Scheme 2), confirmed by MALDI-TOF MS of the organic material cleaved from the bead by reaction with TFA (Fig. 1a).…”

“…Reactions on the solid phase were performed with reagents in large excess followed by filtration of the resin and repeated washing with swelling solvents in which both reagents and non-resin-bound species were soluble. Deprotonation of 6,69-di(hydroxymethyl)-2,29-bipyridine 11 1 (NaH, DMF) followed by reaction with chloromethyl-form Merrifield resin gave a B-functionalised bead 2. This was characterised using magic angle spinning nano-probe 1 H NMR which revealed the expected B aromatic signals (d 7.27 (7.17), 7.22 (7.41), 7.57 (7.69), 7.73 (7.79), 8.14 (8.18), 8.35 (8.32) ppm, 6-hydroxymethyl-69-methyl-2,29-bipyridine in CD 3 OD solution in parentheses).…”

A Versatile Strategy for the Synthesis of Functionalized 2,2‘-Bi- and 2,2‘:6‘,2‘ ‘-Terpyridines via Their 1,2,4-Triazine Analogues

“…On the basis of functionalized 2,2‘-bipyridine and 2,2‘:6‘,2‘ ‘-terpyridine ligands and their complexes, highly sensitive analytical reagents, various sensor systems, − reagents for enantioselective synthesis, and luminescent agents for labeled peptide synthesis were created. 2,2‘:6‘,2‘ ‘-Terpyridines are attractive building blocks for supramolecular chemistry too. , Due to their high emission quantum yields, bi-and terpyridines bearing aromatic substituents in the β-position are particularly interesting for photophysical applications. , …”

Electroactive, Internal Anthraquinonoid Dendritic Cores1

“…As a consequence, a two-electron reduction of the nitroso derivative to yield the hydroxylamine takes place at the same potential of that corresponding to the second wave. As a result of these coupled chemical and electrochemical reactions, the second reduction wave is larger than the first one and the anodic part of the voltammogram does not reveal the oxidation of the anion radical formed during the negative scan …”