Dr. Alexander Seed: "Organic Synthesis: New Heterocyclic Methodology, Synthesis of HNO Donors, Liquid Crystal Synthesis"
Undergraduate research is carried out in collaboration with Dr. Sampson in two main focus areas.
New Heterocyclic Methodology in Liquid Crystal Synthesis
The main focus of our work is in the development of new synthetic heterocyclic methodology and its application to the synthesis of new materials for ferroelectric display and non-display applications. Our current undergraduate projects include the development of 1,3,4-thiadiazole (1 and 2), thieno[3,2-b]thiophene (3), and thieno[2,3-b]thiophene (4) targets such as those shown below:
These new materials have promising physical properties and are critical to the development of materials for cutting-edge electro-optic applications such as ferroelectric displays.
Synthesis of Photoactivatable Nitroxyl (HNO) Donors
HNO shows great promise as a molecule for the treatment of heart failure. We are interested in making new molecules that, when exposed to light, will photochemically decompose to give HNO in a rapid and targeted way.
Students in the Seed/Sampson group receive a broad lab-based education and are exposed to modern synthetic methodology, advanced synthetic techniques (use of pyrophoric reagents under inert atmospheres and cryogenic temperatures, use of hydrogenation rigs, hands-on use of multinuclear NMR machines etc.), and materials analysis (optical microscopy and differential scanning calorimetry). The experience received provides students with an excellent preparation for graduate school and many of our undergraduates have graduated to outstanding Ph.D. programs at University of Illinois (Urbana-Champaign), UCLA, University of Michigan etc. Interested students should contact Dr. Seed or Dr. Sampson after they have successfully completed both CHEM30481 and CHEM 30475.
Selected Publications
A.J. Seed, J.I. Tietz, R.M. Gipson, Y. Yu, and P. Sampson, Low Molar Mass Thieno[3,2-b] and Thieno[2,3-b]thiophenes in Liquid Crystal Materials Science: Recent Synthetic Approaches, Liq. Cryst., 2015, 42(5-6), pp. 918-927.
J.I. Tietz, A.J. Seed, and P. Sampson, Preparation of brominated 2-alkoxythiophenes via oxidation and etherification of 2-thienyltrifluoroborate salts. Org. Lett., 2012, 14(19), pp. 5058-5061.
A.M. Grubb, M.J. Schmidt, A.J. Seed, and Paul Sampson, Convenient preparation of halo-1,3-thiazoles: Important building blocks for materials and pharmaceutical synthesis, Synthesis, 2012, 44(7), pp. 1026-1029.
C. Zhang, A.M. Grubb, A.J. Seed, P. Sampson, A Jákli, and O.D. Lavrentovich, Nanostructure of edge dislocations in a smectic-C liquid crystal, Phys. Rev. Lett., 2015, 115 (8), article no. 08780.
A. Seed, Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core, Chem. Soc. Rev., 2007, 36(12), pp. 2046-2069.