Heemstra Jennifer M, Moore Jeffrey S
Department of Chemistry, 600 South Mathews Avenue, The University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA.
Org Lett. 2004 Mar 4;6(5):659-62. doi: 10.1021/ol0363016.
Incorporation of a pyridine monomer into the backbone of a m-phenylene ethynylene oligomer allows functionalization of the interior binding cavity of the folded oligomer. The basicity of the inwardly directed pyridine moiety was modulated by changing the substituents on the pyridine ring and through oligomer folding, granting access to a pK(a) range of 5-14 in acetonitrile. [reaction: see text]
