Optimization of the Synthesis of n-Phthalimidoalkylthiols as Precursors for w-Aminoalkylthiols as Prepared by Undergraduate Chemistry Students

The synthesis of n-phthalimidoalkylthiols from phthalimide and n,m-dibromoalkane was demonstrated as a general approach to short and medium chain (x = 1 to 12) functional alkylthiols in an undergraduate laboratory setting. The reaction conditions were demonstrated to be mild enough to directly synthesize nphthalimidoalkylthiols with a carbon chain containing either double or triple bonds. The syntheses of each of these alkylthiols can be completed in less than 24 h (over a few laboratory periods) with at least a 50% overall yield. Reactivity of n,m-dibromoalkane with phthalimide was monitored with 1 H-NMR to determine the length of time needed for the reaction to reach completion avoiding the inaccurate use of thin layer chromatography. Based on this result, reaction times were reduced by two-thirds from those previously reported in the literature, which was necessary to prepare a method that will accommodate the duration of second year introductory organic or organic spectroscopy courses

Utilizing the photothermal effect for releasing molecules from the surfaces of gold nanoparticles

Nanomaterials, with unique physical and chemical properties, have the potential to help in the development of drug delivery systems. Some of these properties can be attributed to the nanoscale dimension of these materials. By masking, targeting, and release of a therapeutic agent, these nanomaterials can provide a delivery system that would reduce side effects. Gold nanoparticles have been studied as a candidate for the drug delivery system. These materials can be decorated with molecules that have a thermally responsive reaction (i.e., Diels-Alder). In addition, gold nanoparticles when irradiated with a right wavelength of light produce heat. Consequently, the generated heat from nanoparticles causes a retro-Diels-Alder reaction, which release a segment of molecule (i.e., payload) from gold surfaces. This controlled release mechanism is a novel method to take advantage of the properties inherent in gold nanoparticles and have the potential to be used in drug delivery system