Synthesis of New Organic Materials
Research in the Maly lab focuses on the synthesis of organic compounds that are designed to self-assemble in predictable ways to produce functional materials. Specifically, we are interested in developing methods for the synthesis of novel polycyclic aromatic hydrocarbons that are expected to exhibit columnar liquid crystal phases, as well as the synthesis of novel porous organic networks from small molecule building blocks.
New Polycyclic Aromatic Hydrocarbons
Polycyclic aromatic hydrocarbons (PAHs) have molecular properties that make make them potentially useful for applications in organic electronics. We are interested in the synthesis of new PAHs and exploring their self-assembly and potential to form discotic liquid crystal phases. For example, we make use of a palladium-catalyzed aryne cycotrimerization reaction to prepare compounds such as the substituted trinaphthylene (shown below).
For more information, see: Philip T. Lynett and Kenneth E. Maly, Org. Lett. 2009, 3726-3729.
We are currently pursuing the synthesis of different disk-shaped PAHs, such as hexaalkoxy-substituted dibenzanthracenes. These compounds are prepared from simples precursors using Suzuki-Miyaura cross-coupling, followed by oxidative cyclization. These compounds also offer the opportunity for further synthetic transformations by electrophilic aromatic substitution. These materials exhibit broad columnar liquid crystal phases, as shown by polarized optical microscopy and differential scanning calorimetry.
New Microporous Solids
Microporous solids (possessing pores smaller than 2nm) are materials with potential applications in areas such as gas storage, catalysis, and size-based separations. Our research in this area focuses on the synthesis of new microporous solids based on rigid organic building blocks. In particular, we use rigid molecules such as spirobifluorenes and iptycenes to prepare extended three-dimensional frameworks. We are also interested in controlling the properties of these materials by postsynthetic covalent modification of the materials.
For more information, see: Kenneth E. Maly, J. Mater. Chem., 2009, 19, 1781-1787.