The purpose of this study was the synthesis of novel degradable polymer-based devices capable of releasing an encapsulated agent in a controlled manner with specific interest for use as drug delivery materials. Base-catalyzed thiol Michael additions between trithiols and triacrylates containing silyl ether groups were exploited to prepare a series of degradable cross-linked networks. Disodium fluorescein was loaded as a hydrophilic drug surrogate inside the networks, and the degradation of the networks and the release of dye were monitored. The networks were characterized by Fourier transform infrared spectroscopy, and their thermal and mechanical properties were investigated through thermogravimetric analysis and dynamic mechanical analysis. The effects of the monomer structure on degradation, release behavior, and thermal properties were investigated. The networks prepared from more sterically hindered silyl ether monomers exhibited decreased rates of degradation and correspondingly slower release of encapsulated disodium fluorescein dye. The results suggest that the characteristics of the networks can be fine-tuned by manipulation of the group attached to the Si atom in the silyl ether monomers.
New naphthalene-and perylene-containing polyarylene poly(amic acid)s and polyimides were synthesized from a new phenylated phenylenediamine. A small-molecule model compound was also synthesized with naphthalene end-groups. The new compounds were characterized, and the structures were confirmed using 1 H NMR and attenuated total reflectance Fourier transform infrared spectroscopy. Thermal characterization was conducted using thermogravimetric analysis and differential scanning calorimetry. Onset of thermal degradation temperatures for the naphthalene and perylene polyimides were 561 and 545°C, and char yields at 1000°C were 61 and 59% (under nitrogen), respectively. The glass transition temperatures were 381 and 396°C, respectively. Molecular weights determined using gel permeation chromatography were M w = 35 000 and 24 000 g mol −1 , respectively. The absorption maxima were at 387 and 427/458/491/527 nm, respectively, while the fluorescence emission maxima were at 498 and 541/582 nm, respectively. Nanoparticles were prepared from these new fluorescent dye-containing polyarylene polyimides with sizes of 102/397 and 177 nm, respectively, as determined using dynamic light scattering.
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