Education

B.S., 1993, St. Lawrence University
M.Ed., 1997, St. Lawrence University
Ph.D., 2000, University of Texas - Austin

Honors and Awards

Teva USA Scholar, 2012-2015;  Mortar Board Excellence in Teaching Award, 2012;  Michael J. Mungo Undergraduate Teaching Award, 2009;  Golden Key Faculty Award for Creative Integration of Research and Teaching, 2007;  Distinguished Undergraduate Research Mentor Award, 2007;  Research Corporation Research Innovation Award, 2004-2009.

Research Interests

Molecular recognition, supramolecular chemistry, sensors, materials, bio-organic, physical organic.

The overriding goal in our lab is to understand and predictably control how molecules interact in order to develop new self-assembled materials for real world applications. For example, these assemblies can serve as diagnostics for cancer and food spoilage, as nano-porous materials for gas storage and separation, as novel conjugated polymers for use in OLEDs and PVs, and as new age plastics.

Students are involved in the design, synthesis and analysis phases for each project. Computational methods are often used to aid in molecular design. Organic synthesis provides the foundation to build-in the interactions that control the assembly process and ultimately define the materials' properties. Finally, analytical methods (e.g. optical spectroscopy, mechanical, electronic) are used to assess the assembly performance. Ultimately we enjoy projects where an end use beyond the lab is imaginable (often resulting in patents). With this in mind, the research experience gained in the group is often coupled to a bio-medical or engineering component. In our efforts we work with three general types of compounds: boronates, conjugated polymers and peptides.

Boronates: Novel self-assembling boronate-linked materials have been generated as linear polymers, conjugated materials, and nano-porous covalent organic frameworks (COFs). Given that this interaction is covalent yet reversible, these assemblies form with high fidelity. Boronate ester formation maintains all of the desired attributes of self-assembling materials including ease of synthesis and dynamic self-repair while at the same time offering stable, covalently-linked materials by a route oftentimes more facile and with higher efficiency than conventional polymer synthesis. Boronate-linked specialty plastics exhibit self-repair capabilities and environmental responsiveness. Conjugated poly(boronate)s serve as novel photonic materials and sensitive sensors. Porous COFs and coordination polymers find utility in separations, sequestration, storage, sensing and catalysis. We continue to investigate the mechanical, optical and adsorption properties of these unique materials.

Conjugated Polymers: Using conjugated polymers that interact with small molecules and proteins we have created cross-reactive "aggregative" sensors whose response is defined by the size, shape and valency of the analyte. For example, a colorimetric sensing approach has been developed that can produce a response visible to the naked eye to determine the freshness of foods as a function of spoilage. A simple, point-of-use dipstick has been developed to assess food quality in restaurants and at home. Advanced analysis can be used to deconvolute complex samples and simplify the device read-out. Studies to detect analytes such as proteins and small molecule biomarkers produce diagnostics for diseases such as cancer and HIV. This concept also investigates how small molecule additives can tune the electronic properties of the polymer-additive assemblies, for use in photonic applications.

New synthetic protocols, based on post-polymerization modifications, are developed to modularly incorporate diverse functionality. This design allows for the rapid generation of new compounds and screening of properties to identify the most interesting candidates for new photonic and sensory materials.

Peptides: Synthetic lectins (SLs) are created to bind glycans and glycoproteins associated with numerous disease states. Specifically, SLs have identified aberrant glycosylation patterns associated with colorectal and other cancer types. These unique compounds have been used as in vitro diagnostics and hold great potential as in vivo imaging agents and therapeutics.

Selected Publications

Cai, M.; Daniel, S. L.; Lavigne, J. J. Conjugated Bis and Poly(dioxaborole)s for Optical Sensing of Lewis Bases Based on Main-Chain Perturbations. Chem. Commun. 2013, 49, 6504 - 6506.

Bicker, K. L.; Sun, J.; Harrell, M.; Zhang, Y.; Pena, M. M.; Thompson, P. R.; Lavigne, J. J. Synthetic Lectin Arrays for the Detection and Discrimination of Cancer Associated Glycans and Cell Lines. Chem. Sci. 2012, 3, 1147 - 1156.

Lanni, L. M.; Tilford, R. W.; Bharathy, M.; Lavigne J. J. Enhanced Hydrolytic Stability of Self-Assembling Alkylated 2-Dimensional Covalent Organic Frameworks. J. Am. Chem. Soc. 2011, 133, 13975 – 13983.

Bicker, K. L.; Sun, J.; Lavigne, J. J.; Thompson, P. R. Boronic Acid Functionalized Peptidyl Synthetic Lectins: Combinatorial Library Design, Selective Recognition of Glycoproteins, and Differentiation of Carcinogenic Cell Types. ACS Combi. Sci. 2011, 13, 232 – 243.

Rambo, B. M.; Lavigne, J. J. Defining Self-Assembling Linear Oligo(dioxaborole)s. Chem. Mater. 2007, 19, 3732 - 3739.