title: Exploring and expanding the structural diversity of self-assembling dendrons through combinations of AB, constitutional isomeric AB2, and AB3 biphenyl-4-methyl ether building blocks.
abstract: General, efficient and inexpensive methods for the synthesis of dendritic building blocks methyl 3',4'-dihydroxybiphenyl-4-carboxylate, 3',5'-dihydroxybiphenyl-4-carboxylate, and methyl 3',4',5'-trihydroxybiphenyl-4-carboxylate were elaborated. In all syntheses the major step involved an inexpensive Ni(II)-catalyzed Suzuki cross-coupling reaction. These three building blocks were employed together with methyl 4'-hydroxybiphenyl-4-carboxylate in a convergent iterative strategy to synthesize seven libraries containing up to three generations of 3',4'-, 3',5'-, and 3',4',5'-substituted biphenyl-4-methyl ether based amphiphilic dendrons. These dendrons self-assemble into supramolecular dendrimers that self-organize into periodic assemblies. Structural and retrostructural analysis of their assemblies demonstrated that these dendrons self-assemble into hollow and non-hollow supramolecular dendrimers exhibiting dimensions of up to twice those reported for architecturally related dendrons based on benzyl ether repeat units. These new dendrons expand the structural diversity and demonstrate the generality of the concept of self-assembling dendrons based on amphiphilic arylmethyl ethers.
authors.affiliation: Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA. percec@sas.upenn.edu
authors.forename: Virgil
authors.initials: V
authors.lastname: Percec
authors.forename: Marian N
authors.initials: MN
authors.lastname: Holerca
authors.forename: Sami
authors.initials: S
authors.lastname: Nummelin
authors.forename: John J
authors.initials: JJ
authors.lastname: Morrison
authors.forename: Martin
authors.initials: M
authors.lastname: Glodde
authors.forename: Jan
authors.initials: J
authors.lastname: Smidrkal
authors.forename: Mihai
authors.initials: M
authors.lastname: Peterca
authors.forename: Brad M
authors.initials: BM
authors.lastname: Rosen
authors.forename: Satoshi
authors.initials: S
authors.lastname: Uchida
authors.forename: Venkatachalapathy S K
authors.initials: VS
authors.lastname: Balagurusamy
authors.forename: Monika J
authors.initials: MJ
authors.lastname: Sienkowska
authors.forename: Paul A
authors.initials: PA
authors.lastname: Heiney