2005
DOI: 10.1021/jo050798a
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Synthesis of Crescent Aromatic Oligoamides

Abstract: [structures: see text] This article describes the synthetic procedures for the preparation of crescent (and helical) aromatic oligoamides developed in recent years in our laboratory. The large-scale preparation of a variety of monomers derived from various tetrasubstituted benzenes is presented. Three different strategies for constructing various oligomers consisting of meta- and meta/para-linked benzene residues are discussed. Factors affecting coupling efficiency and yields are analyzed. The developed synthe… Show more

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Cited by 53 publications
(45 citation statements)
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“…In attempts to control the absolute helicity of the metallofoldamer, a different salophen (oligomeric ligand 6, Figure 5) was designed to stabilize the (M)-helix by a threecenter hydrogen bond [20] while destabilizing the (P)-helix through steric interference of the amide carbonyl, by ad- ditional ester functions. Accordingly, ligand 6 was synthesized and mixed with Ni(OAc) 2 to obtain the corresponding Ni complex (oligomer 5, Figure 5).…”
Section: Folding Of Linear Oligomersmentioning
confidence: 99%
“…In attempts to control the absolute helicity of the metallofoldamer, a different salophen (oligomeric ligand 6, Figure 5) was designed to stabilize the (M)-helix by a threecenter hydrogen bond [20] while destabilizing the (P)-helix through steric interference of the amide carbonyl, by ad- ditional ester functions. Accordingly, ligand 6 was synthesized and mixed with Ni(OAc) 2 to obtain the corresponding Ni complex (oligomer 5, Figure 5).…”
Section: Folding Of Linear Oligomersmentioning
confidence: 99%
“…They were dried under vacuum for at least 48 h before use and the concentrations of their stock solutions were standardized by complexometry using xylenol orange as coloured indicators [23,24]. 1,5-Dimethoxy-2,4-diaminobenzene 3 and 2,4-dimethoxy-5-nitroaniline 7 were obtained from reduction of 1,5-dimethoxy-2,4-dinitrobenzene [25]. Diacid chlorides 6 (a, b, c) were prepared from oxalyl chloride and their corresponding diacids, and 4 was synthesized according to similar literature procedures [25].…”
Section: Methodsmentioning
confidence: 99%
“…Polymer P4 was prepared from the reaction of 10 and 11 [32] as a white solid according to a procedure similar to that for the preparation of P1.…”
Section: Polymer P4mentioning
confidence: 99%