This award is made in the Advanced Materials and Processing Program of the Chemistry Division in support of the research of Prof. Thomas Katz. The focus of this research is the rational development of ways to make a variety of helicenes, to obtain them optically active, and to link them together to produce ones much larger than available before.The Diels-Alder reactions of enol ethers of bis-acetophenones and related nitrogen and sulfur compounds will be studied as routes to the helicenes. A number of ways will be evaluated to obtain the helicenes optically active, including a new method using amine adducts of quinones. The methods to be studied for linking helicenes will include one using the Diels-Alder reaction, a second using photocondensations, a third involving a unique trimerization, a fourth using charge-transfer complexes, and a fifth using coordination complexation. The synthetic approaches will allow helicenes to be made in large quantities which has not been possible before. The synthesized helicenes should have novel optical properties, including very large rotational strengths, electronic absorptions at very low wavelengths, and nonlinear optical coefficients, which may impart unique material properties to these compounds. %%% Professor Katz will focus his work on the rational development of ways to make a variety of helicenes, which are helical molecules with unbroken chains of conjugated electrons that wind in one direction. The synthetic approaches will allow helicenes to be made in large quantities which has not been possible before. The novel optical properties of these helicenes may impart unique material properties to these compounds allowing them to be used to make high-density optical storage devices and new liquid-crystalline phases.
