New synthetic methods and organic synthesis

We are interested in developing new methods for constructing sophisticated molecular frameworks that can be used in the synthesis of targeted organic molecules and natural products.  In particular, we are exploring strategies based on dearomatization along with transition metal-mediated transformations for the preparation versatile synthetic building blocks.

Lewis acid promoted dearomatization of substituted pyridines

Parameswarappa, S. G.; Pigge, F. C. Org. Lett. 2010, 12, 3434.; Parameswarappa, S. G.; Pigge, F. C. Tetrahedron Lett. 2011, 52, 4357.


Benzylic cyclizations of substituted pyridines


Parameswarappa, S. G.; Pigge, F. C. J. Org. Chem. 2012, 77, 8038.

Ruthenium mediated dearomatization

Pigge, Coniglio, and Dalvi, J. Am. Chem. Soc. 2006, 128, 3498.; Pigge and Dalvi, Tetrahedron 2008, 64, 10123.; Pigge, Dhanya, and Hoefgen, Angew. Chem., Int. Ed. 2007, 46, 2887.; Pigge, Dhanya, and Swenson, Organometallics 2009, 28, 3869.


Supramolecular chemistry and organic materials

We seek to harness desirable molecular properties exhibited by relatively small organic molecules in larger assemblies constructed via supramolecular (non-covalent) interactions.  Current work is focused on exploiting the electronic and optical properties of tetraphenylethylene (TPE) derivatives in new organic and metal organic materials.

Examples of TPE derivatives as supramolecular building blocks

Semiconducting crystals prepared from TPE tetraacid and bis(pyridine)s

Kapadia, Ditzler, Baltrusiatis, Swenson, Tivanski, & Pigge, J. Am. Chem. Soc. 2011, 133, 8490.

Fluorescent Zn(II) - (Pyridyl)TPE metal-organic framework

Fluorescent halogen-bonded co-crystals of a tetrapyridyl TPE derivative

Pigge, Kapadia, & Swenson, CrystEngComm 2013, 15, 4386.


New bio-conjugation agents for medical imaging

In this project we seek to develop synthetic routes to targeted optical and radio-imaging agents.  This work is part of a collaborative effort with the Schultz lab in the Department of Radiology  aimed at establishing new approaches to radio-diagnostics and therapy.

Cu-Free click chemistry for attachment of radionuclide chelators to peptide ligands

PET imaging of melanoma tumors after metalation with 64Cu

Schultz, Parameswarappa & Pigge, Org. Lett. 2010, 12, 2398.;  Baumhover, Martin, Parameswarappa, Kloepping, O’Dorisio, Pigge & Schultz, Bioorg. Med. Chem. Lett. 2011, 21, 5757.