Creation of Adamantane Polymers Using Organic Synthesis
Presentation Date
7-2015
Abstract
Diamondoids are a unique set of pure carbon clusters that feature the tetrahedral structure of diamond. Like its namesake, these diamondoids are highly symmetrical and crystalline. Adamantane contains 10 carbons in its chemical structure, making it the smallest and simplest diamondoid. Polymers incorporating diamondoids are relatively unexplored, though they can have great potential for nano-technology applications. Thus, research will explore a three step sequence to synthesize adamantane polymers. The first step is to incorporate a dichloromethyl functionality onto the adamantane using a phase-transfer. This reaction is characterized by the use of adamantane dissolved in an organic solvent with chloroform, where the phase transfer catalyst a shuttles strong base, hydroxide, from the water layer to produce dichlorocarbene to attack the adamantane cluster. The second step will be an acid or base hydrolysis to add a carbonyl functionality onto the adamantane. Finally, a Wittig reaction will exchange the oxygen in the carbonyl group with a methylene unit to form the vinyl group and give an olefin monomer suitable for chain growth polymerization and block copolymers.
Creation of Adamantane Polymers Using Organic Synthesis
Diamondoids are a unique set of pure carbon clusters that feature the tetrahedral structure of diamond. Like its namesake, these diamondoids are highly symmetrical and crystalline. Adamantane contains 10 carbons in its chemical structure, making it the smallest and simplest diamondoid. Polymers incorporating diamondoids are relatively unexplored, though they can have great potential for nano-technology applications. Thus, research will explore a three step sequence to synthesize adamantane polymers. The first step is to incorporate a dichloromethyl functionality onto the adamantane using a phase-transfer. This reaction is characterized by the use of adamantane dissolved in an organic solvent with chloroform, where the phase transfer catalyst a shuttles strong base, hydroxide, from the water layer to produce dichlorocarbene to attack the adamantane cluster. The second step will be an acid or base hydrolysis to add a carbonyl functionality onto the adamantane. Finally, a Wittig reaction will exchange the oxygen in the carbonyl group with a methylene unit to form the vinyl group and give an olefin monomer suitable for chain growth polymerization and block copolymers.