ORGN 286 |
| The synthesis of “designer” dendrimers and dendrons with sulfonimide units at every branching point is based on series of (regio)selective functionalization reactions of amines and sulfonamides allowing to precisely control the dendrimers' shape, the number of branches in each generation, and their peripheral decoration with functional groups. By utilizing the selectivities inherent in the reactions, no complicated protective group strategy is required. In principle, structurally different branches can be incorporated at any position within the dendrimer structure at will. Structurally perfect symmetrical and two-faced “Janus”-type dendrimers, as well as dendrimers and dendrons with intended interstices were synthesized on a preparative scale and fully characterized. Oligosulfonimide dendrons of various generations bearing an aryl bromide functional group at their focal points were attached to a p-phenylene core with the aid of Suzuki cross-coupling reactions resulting in dendrimers with photoactive terphenyl cores. Dendritic oligosulfonimides and their polymers self-organize in the crystalline state and form well-defined aggregates in solution and at interfaces.
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Materials, Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Monday, 11 September 2006 Moscone Center -- Room 132, Oral
Division of Organic Chemistry |
