Dr. Paul Sampson: "Organic Synthesis: Synthesis of HNO Donors, Liquid Crystal Synthesis, Reaction Development"

Undergraduate research in the Sampson group is focused on collaborative programs with Dr. Seed in two main areas, both of which emphasize the use of modern organic synthesis to prepare targets with useful biological or materials properties:

Synthesis of Photoactivatable HNO Donors

There is much current interest in HNO (nitroxyl), a small biologically relevant molecule which shows clinical promising activity relating to cardiovascular health.   Since HNO itself is not stable in aqueous solution, we are synthesizing new “HNO donors” such as 1 and related analogs which rapidly decompose on irradiation with light to release HNO.   Fundamental photochemical studies on these compounds are also conducted in our lab.  The most promising compounds are used by our collaborators in New Zealand to probe the bioinorganic chemistry of HNO.

Synthesis of Ferroelectric Liquid Crystalline Materials

We are pursuing the synthesis of new families of liquid crystalline materials containing various S-heterocyclic rings within their core structure, some decorated with fluoro substituents (e.g. 2, 3).  The targeted compounds exhibit a particular type of liquid crystal phase (the smectic C phase) and have promise for use in ferroelectric liquid crystal displays.  

Students in the Sampson/Seed group receive broad exposure to the field of target-oriented multi-step organic synthesis as well as to the development of new synthetic methods.  You will learn how to perform a variety of modern reactions (e.g., working with air-sensitive reagents, low temperature chemistry) and will use high-field NMR and other techniques for product characterization.  The breadth of skills gained during this research experience constitutes an excellent preparation for a career in industry or graduate school.  Recent undergraduates from our lab have moved on to top chemistry Ph.D. programs (U of Illinois Urbana-Champaign, U of Michigan, UCLA) and dental schools (Columbia U, U of Maryland).  Interested students who have successfully completed both CHEM 30481 and 30475 are encouraged to discuss research opportunities with Dr. Sampson and/or Dr. Seed.

Representative Publications (undergraduate co-authors in bold)
  • “Low molar Mass Thieno[3,2-b] and Thieno[2,3- b]thiophenes in Liquid Crystal Materials Science: Recent Synthetic Approaches,” Seed, A. J.; Tietz, J. I.; Gipson, R. M.; Yu, Y.; Sampson, P. Liquid Crystals 2015, 42, 918-927.
  • “Novel 5-(4-Alkoxyphenyl)thieno[3,2-b]thiophene-2-carboxylate Esters: Highly Efficient  Synthesis and Mesogenic Evaluation of a New Class of Materials Exhibiting the Smectic C Phase,” Tietz, J.I.; Mastriana, J.R.; Sampson, P.; Seed, A.J. Liquid Crystals 2012, 39, 515-530.
  • “Convenient Preparation of Halo-1,3-thiazoles: Important Building Blocks for Materials and Pharmaceutical Synthesis,” Grubb, A.M.; Schmidt, M.J.; Seed, A.J.; Sampson, P. Synthesis 2012, 44, 1026-1029.