Tripodal oxazolines

Substantial efforts have been devoted to the development of molecular sensors for dopamine. Raymo et al.70 reported a two-step procedure to coat silica particles with fluorescent 2,7-diazapyrenium dications sensing toward dopamine. The analysis of the fluorescence decay with multiple-equilibria binding model revealed that the electron deficient dications and the electron-rich analytes form 1 1 and 1 2 complexes at the particle/water interface. The interfacial dissociation constants of the 1 1 complexes were 5.6mM and 3.6mM for dopamine and catechol, respectively. Dopamine was dominated by the interaction of its electron-rich dioxyarene fragment with the electron-deficient fluorophore in neutral aqueous environments. Ahn et al.71 reported tripodal oxazoline-based artificial receptors, capable of providing a preorganized hydrophobic environment by rational design, which mimics a hydrophobic pocket predicted for a human D2 receptor. A moderate binding affinity, a dissociation constant of 8.2 mM was obtained by NMR titrations of tripodal oxazoline-based artificial receptor with dopamine in a phosphate buffer solution (pH 7.0). Structurally related ammonium ions, norepinephrine, 2-phenylethylamine,... 

The natural product westiellamide (158) and other unnatural cyclopeptide alkaloids were synthesised by cyclooligomerisation reactions <00T9143>. The benzene-based tripodal tris(oxazolines) 159 were developed as new selective receptors toward alkylammonium ions <00CEJ3399>. 

Additionally, the synthesis of tripods with mixed substitution patterns (B-D, including the inversion of chiral centers as in B) was achieved in excellent yields [13]. This opened up the possibility to approach the synthesis of such polydentate oxazolines in a modular way, including tripods with mixed stereochemistry, that is, partially inverted chiral centers as well as achiral oxazoline rings. 

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