Research Overview

Our research focuses on the synthesis of both small molecules and macromolecules (oligomers and polymers) that have been designed to perform a particular function. Projects within the group include the design and synthesis of molecular muscles (a.k.a. electromechanical actuators), double helical macromolecules, molecule-based electrooptical switches, conjugated molecules with novel architectures, and potential phototherapeutic anticancer drugs. We make extensive use of conjugation to impart onto our materials interesting optical and electronic properties. Students working on a particular project assist in project development, synthesis, and the design of experiments directed at demonstrating that the materials function as planned. As such, students in the group are exposed to a very interdisciplinary approach to chemistry. Our research has been made possible through the generous support of the National Science Foundation, Research Corporation, DuPont, and the Petroleum Research Fund (administered by the ACS).

Selected Publications

(13) Marsella, M. J.; Reid, R. J. Toward molecular muscles: Design and synthesis of an electrically conducting poly[cyclooctatetrathiophene]. Macromolecules 1999, 32, 5982-5984.

(14) Marsella, M. J.; Wang, Z. Q.; Mitchell, R. H. Backbone photochromic polymers containing the dimethyldihydropyrene moiety: Toward optoelectronic switches. Organic Letters 2000, 2, 2979-2982.

(15) Marsella, M. J.; Kim, I. T.; Tham, F. Toward conjugated double helical ladder polymers: Cyclooctatetrathiophene as a highly versatile double helical scaffold. Journal of the American Chemical Society 2000, 122, 974-975.

(16) Marsella, M. J.; Meyer, M. M.; Tham, F. S. Dewar benzene as a protecting group? Demonstration of photolithographic crystallization. Organic Letters 2001, 3, 3847-3849.

(17) Marsella, M. J.; Yoon, K.; Tham, F. S. Synthesis and crystal structure of a tubular sexithiophene. Organic Letters 2001, 3, 2129-2131.

(18) Marsella, M. J.; Wang, Z. Q.; Reid, R. J.; Yoon, K. Synthesis of acetylenic cyclophanes via intramolecular self- assembly: Evidence of perfluorophenyl-phenyl quadrupole interactions in the solution state. Organic Letters 2001, 3, 885-887.

(19) Marsella, M. J.; Reid, R. J.; McCormick, M. T. A new technique for monitoring real-time dimensional changes in polymeric electromechanical actuators and vaporesistive sensors. Synthetic Metals 2001, 118, 171-174.

(20) Marsella, M. J.; Piao, G. Z.; Tham, F. S. Expanding tetra[2,3-thienylene]-based molecular muscles to larger [4n]annulenes. Synthesis 2002, 1133-1135. Invited.

(21) Marsella, M.J. Classic annulenes, nonclassical applications. Accounts of Chemical Research 2002, 35, 944-951. Invited; Cover art

(22) Marsella, M.J.; Reid, R.J.; Estassi, S.; Wang, L.S. Tetra[2,3-thienylene]: A building block for single-molecule electromechanical actuators. Journal of the American Chemical Society 2002, 124, 12507-12510.

(23) Mitchell, R. H.; Ward, T. R.; Chen, Y.; Wang, Y.; Weerawarna, S. A.; Dibble, P. W.; Marsella, M. J.; Almutairi, A.; Wang, Z.-Q. Synthesis and photochromic properties of molecules containing [e]-annelated dihydropyrenes. Two and three way switches based on the dimethyldihydropyrene-metacyclophanediene valence isomerization. Journal of the American Chemical Society 2003, 125, 2974-2988.

(24) Marsella, M. J.; Yoon, K.; Almutairi, A.; Butt, S.K.; Tham, F. Helical sexithiophenes: An experimental and theoretical study implicating the aternating 2,2':3,3' regioisomer as a reliable helical motif. Journal of the American Chemical Society 2003, 125, 13928-13929.

(25) Marsella, M. J.; Estassi, S.; Wang, L.S.; Yoon, K. Revisiting cyclobutadienemetal complexes: High-content Dewar benzene polymers and a one-pot synthesis of permethyleated ladderanes. Synlett 2004, 192-194. Invited.

(26) Almutairi, A.; Tham, F. S.; Marsella, M. J. Ortho-tetraaryls as helical building blocks: A study of structure, theory, electrochemistry, and optical properties Tetrahedron 2004, 60, 7187-7190. Invited.

Book Chapters

(1) M. J. Marsella "Molecular Scale Electroactive Polymers" pp. 249 263; in Electroactive Polymer (EAP) Actuators as Artificial Muscles: Reality, Potential, and Challenges, Y. Bar-Cohen, Ed., SPIE - The International Society for Optical Engineering, Bellingham, WA. 2001. Invited (Dr. Y. Bar-Cohen, Ed.)

(2) M. J. Marsella "Annulenes" in Encyclopedia of Supramolecular Chemistry (ESMC), J. L. Atwood and J. W. Steed, Eds., Marcel Dekker, Inc. | Print Published: 05/05/2004 | Online Published: 08/17/2004, Pages: 59 - 67 DOI: 10.1081/E-ESMC-120019198 Invited.