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.