Reticular Synthesis of Nanoporous Materials Using Triptycene-Based Organic Building Blocks

Nanoporous materials are crystalline frameworks materials including metal-organic frameworks, covalent organic frameworks, and hydrogen-bonded organic frameworks. These materials can be designed and synthesized using the reticular chemistry approach. Reticular chemistry uses underlying geometry arguments of individual molecular building blocks to assemble periodic networks. The toolbox of reticular chemistry includes organic and inorganic building units with versatile geometries. Such a toolbox makes the reticular chemistry approach a powerful tool for designing nanoporous materials with pre-defined network structures. To further develop the capability of reticular chemistry, organic clusters with higher connectivity are needed. This thesis presents triptycene-based organic building units with high connectivity for synthesizing nanoporous materials. We present 1) the first example of a hydrogen-bonded organic framework with a 12-connecting organic building block, 2) the second example of a metal-organic framework with a hexagonal prismatic organic building block, and 3) a 6-connecting organic building block for synthesizing covalent organic frameworks with unprecedented network topologies. The metal-organic framework report in this thesis exhibits excellent performance in selectively capturing methane over nitrogen. The results presented in this thesis demonstrate that triptycene is a powerful precursor toward organic building blocks for nanoporous materials with unique network geometries.