Self-assembly of hybrid dendrons with complex primary structure into functional helical pores.
The synthesis of three libraries of self-assembling hybrid dendrons containing a primary structure based on the sequence (4-3,4-3,5)12G2-CO(2)CH(3) generated from benzyl ether, biphenyl-4-methyl ether, and AB(2) repeat units constructed from (AB)(y)--AB(2) combinations of benzyl ethers, is reported. The structural and retrostructural analysis of their supramolecular dendrimers facilitated the discovery of new architectural principles that lead to the assembly of functional helical pores. The self-assembly of an example of hybrid dendron containing -H, -CO(2)CH(3), -CH(2)OH, -COOH, -COOK, -CONH(2), -CONHCH(3), -CO(2)(CH(2))(2)OCH(3), -(R) and -(S)-CONHCH(CH(3))C(2)H(5) as X-groups at the apex demonstrated that these self-assembling dendrons provide the simplest strategy for the design and synthesis of porous columns containing a diversity of hydrophilic and hydrophobic functional groups in the inner part of the pore. The results reported here expand the scope and limitations of dendrons available for the self-assembly of functional pores that previously were generated mostly from dendritic dipeptides, to simpler architectures based on hybrid dendrons.
Percec
Virgil
V
Roy and Diana Vagelos Laboratories, Department of Chemistry, Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, PA 19104-6323, USA. percec@sas.upenn.edu
Smidrkal
Jan
J
Peterca
Mihai
M
Mitchell
Catherine M
CM
Nummelin
Sami
S
Dulcey
Andrés E
AE
Sienkowska
Monika J
MJ
Heiney
Paul A
PA
D000873:Anthracenes / Q000737:chemistry*; D002942:Circular Dichroism; D015394:Molecular Structure; D014961:X-Ray Diffraction
D000873:Anthracenes; C501244:dendron