Chemical Properties
N-Hydroxynaphthalimide triflate is a low molecular weight compound with the appearance of white to light yellow powder to crystal, melting point is 212.1~214.2 °C, boiling point is 456.2±55.0 °C, density is 1.76±0.1 g/cm
3, maximum absorption wavelength is 365(CH3CN) nm. It is sensitive to light and moisture and is normally stored under inert gas.
Uses
HNT can be used to form patterned nanoparticles that find potential applications in volumetric manufacturing of semiconductor devices. It can also be used in the photo-responsive pore reopening of zeolites that facilitates the regulation of the gas permeation process. UV-irradiated trimethylsilyl ultrathin cellulose based films can be formed in presence of HNT as a PAG.
Application
N-Hydroxynaphthalimide triflate is a cationic photoinitiator and nonionic photoacid generator used for polymer science, contact printing, and self-assembled monolayers (SAMs).
General Description
N-Hydroxynaphthalimide triflate (HNT) is a photoacid generator(PAG) that forms an acid upon exposure to UV light which can be used to generate patterned structures. It can also be used to tune the solubility of a polymer by forming acid linkages.
Synthesis
A mixture of 10.0 g (0.051 mol) naphthalic anhydride, 3.9 g (0.056 mol) hydroxylamine hydrochloride and 80 ml pyridine was taken and stirred at 100 C for 10 hours. After cooling to room temperature, the reaction solution was poured into 1 N hydrochloric acid and the precipitate was recovered by filtration. The resulting precipitate 5.0 g was dissolved in pyridine (50 ml) into which 8.3 g (0.026 mol) of synthesized bis(pentafluoroethyl)phosphinic chloride was added dropwise while stirring at 0 C. After stirring at 25 C for 2 h, the reaction solution was extracted with dichloromethane-water, and the organic layer was removed under reduced pressure to remove the solvent, giving an orange solid. Recrystallization with acetonitrile gave a white solid 5.3 g, 0.01 mol). Bis(pentafluoroethyl)phosphinic chloride was added to trifluoromethanesulfonic acid and the anhydride (7.3 g, 0.028 mol) was substituted for the anhydride to give the crude product, N-hydroxynaphthimide trifluoromethanesulfonate (7.0 g, 0.020 mmol).
