Thiol-ene networks are of current interest to the biomedical and flexible electronics communities due to their synthetic accessibility, uniform network formation and excellent adherence to deposited electrodes. Nevertheless, thiol-ene materials often suffer from hydrolytic instability, due to enchained ester functionalities, and low glass transition, due to the flexible nature of the monomers and the small energy barrier of rotation in the thioether bonds. Therefore, the synthesis of rigid, hydrolytically stable thiol-ene monomers is essential to overcoming these shortfalls. Recently we have developed a synthetic methodology for the facile conversion of a commercially available tricyclic diols to dithiols in three steps. Initial studies with commercially available monomers have yielded polymers which are hydrolytically stable (up to 1 week in 1M NaOH at 37 �C without mass loss) and have high glass transition temperatures for thiolene networks (up to 80 �C) while possessing low crosslink density. Herein we report the polymer and network properties of these new dithiol monomers and their potential application to biomedical devices and flexible electronics.  Figure 1. DMA of novel dithiol network (low crosslink density) versus commercially available trithiol network (high crosslink density).

Rigid dithiols: New monomers for thiolene polymers and networks

247th National Meeting (2014)

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