CAREER: Selective Thiol-Ene and Thiol-Yne Chemistry, From First Principles to Organic Materials

Wesleyan University, Middletown CT

Investigators

Abstract

In this project funded by the Macromolecular, Supramolecular and Nanochemistry Program of the Chemistry Division, Brian Northrop of Wesleyan University is investigating how to direct chemical reactions to form specific linkages between molecules and form polymers. Polymers are long chain organic molecules and are found in many facets of everyday life that utilize plastics, including food packaging, structural materials for automotive and aerospace transportation, and lightweight electronic devices. These insights will provide more efficient methods for making a variety of materials and for creating new types of materials with novel properties. The results of this research are expected to impact applications such as the development of materials for the targeted delivery of drugs, new consumer care products, and new plastic materials. In this project Brian Northrop is investigating the fundamental reactivity of thiols with alkenes and alkynes. The research objectives include first principles computational modeling of thiol-ene and thiol-yne reaction mechanisms, small molecule model studies for synthetic testing of selective thiol-ene and thiol-yne reaction conditions, and implementation of these new methods in the synthesis of organic macromaterials. The project integrates these research goals with outreach programs that include hands-on workshops in polymer science for elementary school students and the development of an interdisciplinary program in materials chemistry that will increase the participation and retention of undergraduate students in the sciences. While both thiol-ene and thiol-yne reactions have found broad utility across multiple areas of polymer and materials chemistry there are, at present, few known methods for carrying out selective thiol-ene and thiol-yne reactions, which this research project addresses. This research should enable the development of more efficient means to prepare complex, multifunctional materials with selectively tunable properties.