Synthesis and Self-Assembly of Supramolecular Dendritic “Bow-Ties”: Effect of Peripheral Functionality on Association Constants
- 8 November 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (1) , 46-53
- https://doi.org/10.1021/jo035329s
Abstract
Self-assembled polyester dendritic bow-ties with various peripheral groups were prepared, and their association constants were measured by (1)H NMR in CDCl(3). The two complementary dendrons were prepared by attachment of either a bis(adamantylurea) or a glycinylurea to the focal point of the dendron. The parent self-assembled system with benzylidene acetals on one periphery and isopropylidene acetals on the other had an association constant of 520 M(-)(1). Upon deprotection of one dendron, the association constant is increased by more than an order of magnitude as the solubility of the hydroxyl-terminated dendron in CDCl(3) is decreased. In contrast, attachment of tri(ethylene oxide) units to the periphery of one dendron lowers the association constant by almost an order of magnitude. The causes of these relatively large changes in complex strength are discussed in terms of solubility, steric effects, competitive hydrogen bonding, and the structure of the dendritic scaffold.Keywords
This publication has 25 references indexed in Scilit:
- Catalysis inside dendrimersChemical Society Reviews, 2002
- Dendritic−Linear AxBx Block Copolymers Prepared via Controlled Ring-Opening Polymerization of Lactones from Orthogonally Protected Multifunctional InitiatorsMacromolecules, 2001
- Synthesis and Structural Analysis of Two Constitutional Isomeric Libraries of AB2-Based Monodendrons and Supramolecular DendrimersJournal of the American Chemical Society, 2001
- Dendrimers Based on Electroactive Metal Complexes. A Review of Recent AdvancesCollection of Czechoslovak Chemical Communications, 2001
- Iron−Sulfur Core Dendrimers Display Dramatically Different Electrochemical Behavior in Films Compared to SolutionJournal of the American Chemical Society, 2000
- Dendrimers Functionalized with a Single Fluorescent Dansyl Group Attached “Off Center”: Synthesis and Photophysical StudiesJournal of the American Chemical Society, 2000
- Synthesis and Catalytic Activity of Unimolecular Dendritic Reverse Micelles with “Internal” Functional GroupsJournal of the American Chemical Society, 1999
- Morphology-Dependent Photochemical Events in Aryl Ether Dendrimer Porphyrins: Cooperation of Dendron Subunits for Singlet Energy TransductionJournal of the American Chemical Society, 1998
- Self-Assembled Lanthanide-Cored Dendrimer Complexes: Enhancement of the Luminescence Properties of Lanthanide Ions through Site-Isolation and Antenna EffectsChemistry of Materials, 1998
- Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromoleculesJournal of the American Chemical Society, 1990