The synthesis and characterization of a highly fluorescent core-substituted naphthalene diimide sensor (varphi = 0.34) bearing a bis-sulfonamide group is described. The compound shows a unique selectivity and reactivity for the fluoride ion over other anions in CHCl(3) by a two-stage deprotonation process leading to a colorimetric response. In DMSO solution, the sensor is shown to be highly selective for fluoride (K(a) approximately 10(6) M(-1)) over other anions with more pronounced changes in absorption characteristics.

a Reaction conditions: 2a (1.0 mmol), boronic acid (3 mmol), 2 mol% Pd(PPh 3 ) 4 , 2 M Na 2 CO 3 (1 mL) and dioxane (3 mL), reflux for 12 h under argon atmosphere. b Isolated yield.

The results of a solvo-controlled self-assembly process involving a novel non-ionic protoporphyrin IX functionalized with triethylene glycol (Proto-NTEG) chains is discussed. In relatively non-polar aprotic solvents (cyclohexane/CHCl3), the protoporphyrin forms stable, uniformly-sized multilamellar micro-vesicles of approximately 65 nm diameter, while in more polar protic solvent mixes (CHCl3/MeOH), the same protoporphyrin forms micellar aggregates with dimensions of approximately 6 nm. The solvo-control operates based on the differing properties of glycol units in cyclohexane and methanol leading to inverse self-assembled structures.