Synthesis and properties of new water-soluble aliphatic hyperbranched poly(amido acids) with high pH-dependent photoluminescence

Abstract

Water-soluble fluorescent hyperbranched poly(amido acids) (HBPAAs), based on wholly aliphatic structures were prepared through direct self-condensation of N-(3-aminopropyl) diethano succinate amine (APDESA, AB2 monomer) in the presence of N,N-dicyclohexylcarbodiimide (DCC) as a condensation agent. The resulting HBPAAs were soluble in water, DMF and THF, and the structure of synthesized AB2 monomer and polymers was confirmed by IR, 1H, and 13C NMR measurements. TEM image indicated that the HBPAAs self-assembled in H2O to form a spherical micelle with a diameter ranging from 30 to 50 nm. A significant pH-dependent profile of fluorescent intensity in the pH range from 3 to 10 was observed, wherein pH 4 provided a critical jump as the solution pH was increased. Further increasing the pH to 10 decreased the fluorescence because of partial hydrolysis. Strong fluorescence emission was observed at 395 nm in aqueous media and the fluorescence quantum yields are to 23%. These amphiphilic HBPAAs, with excellent water-solubility, void-rich space, multiple functional peripheries and high blue fluorescence, have potential uses as tracing nanocarriers and molecular-level containers.