162971-20-2

Upstream product

• 112633-26-8 2,6-bis[(tosyloxy)methyl]pyridine 
• 1195-59-1 2.6-bis(hydroxymethyl)pyridine 
• 123-08-0 4-hydroxy-benzaldehyde 
• 7703-74-4 2,6-bis-(bromomethyl)pyridine 
• 144106-20-7 2,6-bis(4-formylphenoxymethyl)pyridine 
• 162971-19-9 2,6-Di(p-methoxycarbonylphenoxymethyl)pyridine 

Downstream Products

• 261355-65-1 2,6-Di(p-bromomethylphenoxymethyl)pyridine 
• 162971-21-3 2,6-bis(4-chloromethylphenoxy)lutidine 

Relevant academic research and scientific papers

Synthesis of intra-annularly functionalized cationic pyridinophanes

The precyclophane 1 derived from 2,6-bis(bromomethyl)pyridine and 2.1 equiv. of benzimidazole afforded pyridinobenzimidazolophanes 6-8 on further reaction with 1 equiv. of 2,6-bis(bromomethyl)pyridine, 3,5-bis(bromomethyl)anisole and 1,3-bis(bromomethyl)-4-nitrophenol, respectively. A similar synthetic strategy was used for the synthesis of pyridinobenzotriazolophanes 9-11. Potential receptors 16 and 17 were also synthesized.

Synthesis of chiral cyclophanes based on meta-terphenyl and pyridyl blocks

Coupling of m-terphenyl dibromide with binol afforded the corresponding optically active cyclophane. Chiral cyclophanes were also obtained by the coupling of p-nitrophenol or 4,4″-bis(bromomethyl)-1,3-dibenzylbenzene with binol.

Self-complementary [2]catenanes and their related [3]catenanes

Three [3]catenanes with cavities large enough to accommodate aromatic guests have been designed and synthesized (yields = 5-20%) by means of kinetically controlled self-assembly processes. The X-ray structural analysis of one of three [3]catenanes confirmed the presence of a rectangular cavity (dimensions = 7 ×11 A) lined by π-electron-rich recognition sites and hydro-gen-bond acceptor groups. In spite of their apparently ideal recognition features, none of these [3]catenanes bind guests incorporating a π-electron-deficient bipyridinium unit. However, the template-directed syntheses of the [3]catenanes also produce, in yields of 2-23%, [2]catenanes incorporating a l,5-dioxynaphtho[38]crown-10 inter-locked with a bipyridinium-based tetracationic cyclophane. The X-ray structural analyses of two of these [2]catenanes revealed that a combination of [π...π] and [C-H...π] interactions is responsible for the formation of supramolecular homodimers in the solid state. 1H NMR spectroscopic investigations of the four [2]catenanes demonstrated that supramolecular homodimers are also formed (Ka= 17-31M-1, T= 185 K) in (CD3)2CO solutions. Dynamic 1H NMR spectroscopy revealed that the 1,5-dioxynaphtho[38]crown-10 and tetracationic cyclophane components in the four [2]catenanes and in the three [3]catenanes circumrotate (ΔGC? = 9-14 kcal mol-1) through each other's cavity in (CD3)2CO. Similarly, the 1,5-dioxynaphthalene and the bipyridinium ring systems rotate (ΔGc? =10-14 kcalmol-1) about their [O...O] and [N ... N] axes, respectively, in solution.

Meta-terphenyls as Building Blocks for Pyridinophanes

Pyridinophanes 6 and 7 were prepared in good yield from bis(thiomethyl)-m-terphenyls 2 and 12 and bis(chloromethyl)pyridine derivative 11.