Office: 411 Coulter Hall
Email: mattern AT olemiss.edu
Educational and Professional Background
B.A., Kalamazoo College, 1970
M.S., Stanford University, 1971
Ph.D., Stanford University, 1975
Postdoctoral Fellow, Tufts University School of Medicine, 1976
Postdoctoral Fellow, University of California at San Diego, 1977-1979
Research Interests: Organic Donor-sigma-Acceptor molecules, fatty acyl analogs of acarnidine, aromatic iodination
Organic donor-sigma-acceptor molecules. The goal of this project is to prepare compounds containing electron- donor and electron-acceptor groups, separated by a bridge of non-conducting sigma bonds. Each "D-sigma-A" target also typically contains pendant lipid tail(s) to help the molecules assemble as an ordered Langmuir-Blodgett film, or pendant alkyl thiol(s), sulifde(s), or disulfide(s) to help them assemble as an ordered monolayer on a gold surface. Such films may serve to rectify electrical current in molecule-sized circuits, which could lead to tiny electrical devices. In fact, one of our products, utilizing a pyrene donor group and a dinitrobenzyl acceptor group, displays striking rectifying voltage properties when tested as a multilayer.
Our current work involves (1) making new D-sigma-A targets via further elaboration of the good donor pyrene; (2) forming the sigma bridge via Diels Alder reactions between donor-dienes and acceptor-dienophiles; (3) using anhydride chemistry to attach sigma-A and solublizing groups at opposite ends of the annoyingly insoluble compound perylene, which can potentially be converted to either a good donor or a good acceptor; and (4) attaching three thiol tails to model donor molecules in such a way that their orientation on gold electrodes will be forced to be orthogonal.
Aromatic iodination. This work investigates the direct substitution of many iodine atoms onto aromatic rings. We have developed a powerful system (I2 / H4IO6 / H2SO4) for iodinating deactivated aromatics. For example, nitrobenzene and benzoic acid can easily be pentaiodinated. However, the method fails for activated rings; the conditions are too harsh. Our future work involves moderating the reaction conditions to promote high-yield conversions in activated systems such as phenol and the xylenes. Careful 13C-NMR analysis is crucial for this work, as the iodinated products have few protons for 1H-NMR, have few functional groups for IR analysis, and have high molecular weights making mass spectrometry difficult. The iodinated products have become valuable synthetic intermediates as the use of palladium-catalyzed coupling reactions of iodoorganics with alkenes (the Heck reaction) and organotins (the Stille reaction) has grown.
Dr. Mattern is the author of the PushMasterTM electron-pushing skill-builder computer program. PushMaster runs as a HyperStudio multimedia program with the (free) HyperStudio Player. It provides patient and, most importantly, interactive practice in the crucial skill of "pushing electrons" for the understanding of fundamental organic chemistry mechanisms and reactions. PushMaster is currently available on the Ole Miss campus for the Macintosh platform.
Boo, W.O.J.; Mattern, D.L. Concomitant Ordering and Symmetry Lowering The Journal of Chemical Education. 2008, 85, 710-717.
Samudrala, R.; Zhang, X.; Wadkins, R. M.; Mattern, D. L. Synthesis of a Non-Cationic, Water-Soluble Perylenetetracarboxylic Diimide and Its Interactions with G-Quadruplex-Forming DNA. Bioorganic & Medicinal Chemistry 2007, 15, 186-193. doi:10.1016/j.bmc.2006.09.075.
Shumate, W.J.; Mattern, D.L.; Jaiswal, A.; Dixon, D.A.; White, T.R.; Burgess, J.; Honciuc, A.; Metzger, R.M. Spectroscopy and rectification of three Donor-Sigma-Acceptor compounds, consisting of a one-electron donor (pyrene or ferrocene), a one-electron acceptor (perylenebisimide), and a C19 swallowtail. Journal of Physical Chemistry B 2006, 110, 11146-11159.
Davis, S.R.; Nguyen, K.A.; Lammertsma, K.; Mattern, D.L.; Walker, J.E. Ab initio Study of the Thermal Isomerization of Tricyclo[3.1.0.02,6]hexane to (Z,Z)-1,3 Cyclohexadiene through the (E,Z)-1,3-Cyclohexadiene Intermediate. Journal of Physical Chemistry A, 2003; 107; 198-203.
Wescott, L.D.; Mattern, D.L. Donor-Sigma-Acceptor Molecules Incorporating a Nonadecyl-Swallowtailed Perylenediimide Acceptor. Journal of Organic Chemistry 2003
Boo, W.O.J.; Mattern, D.L. Generating Closed Shapes from Regular Tilings. Journal of Chemical Education 2002, 79, 1017-1023 (cover article).
Hu, Jian; Mattern, D.L. Ferrocenyl Derivatives with One, Two, or Three Sulfur Containing Arms for Self Assembled Monolayer Formation. Journal of Organic Chemistry, 2000, 65, 2277-2281.
Yu, Duyi; Mattern, D.L. "Preparation of the three 2,3-dihalo-1,4-benzoquinones." Synthetic Communications
Brady, A.C.; Hodder, B.; Martin, A.S.; Sambles, J.R.; Ewels, C.P.; Jones, R.; Briddon, P.R.; Musa, A.M.; Panetta, C.A.; Mattern, D.L. Molecular rectification with M | (D-sigma-A LB film) | M junctions. Journal of Materials Chemistry, 1999, 9, 2271-2275.
Lee, H.; He, Z.; Hussey, C.L.; Mattern, D.L. Chem. Mater. 1998, 10, 4148. "Unsymmetrical Dialkyl Sulfides for Self-Assembled Monolayer Formation on Gold: Lack of Preferential Cleavage of Allyl or Benzyl Substituents."
Mattern, D.L.; Scott, W.D.; McDaniel, C.A.; Weldon, P.J.; Graves, D.E. J. Nat. Prod., 1997, 60, 828-831. "Cembrene and a congeneric ketone isolated from the paracloacal gland of the Chinese alligator (Alligator sinensis)."
Musa, A.; Sridharan, B.; Lee, H.-Y.; Mattern, D.L. J. Org. Chem. 1996, 61, 5481-5484. "7 Amino-2-pyrenecarboxylic Acid."
Panetta, C.A.; Fang, Z.; Mattern, D.L. J. Org. Chem. 1995, 60, 7953-7958. "Iodination of methylated anisoles: unusual aryl methyl replacements and oxidations."
Mattern, D.L. J. Chem. Educ. 1995, 72, 1092. "Elemental Anagrams Revisited. "
Nadizadeh, H.; Mattern, D.L.; Singleton, J.; Wu, X.-L.; Metzger, R.M. Chem. Mater. 1994, 6, 268-277. "Langmuir-Blodgett films of Donor-sigma-Acceptor (D-sigma-A) compounds, where D = anilide donors with internal diyne or saturated lipid tails, sigma = carbamate bridge, and A = 4-nitrophenyl or TCNQ acceptors."
Heimer, N.E.; Mattern, D.L. J. Am. Chem. Soc. 1993, 115, 2217-2220. "A structural steric isotope effect in deuterated tetracyanoanthraquinodimethane.
Mattern, D.L.; Chen, X. J. Org. Chem. 1991, 56, 5903-5907. "Direct polyiodination of benzenesulfonic acid."
Metzger, R.M.; Wiser, D.C.; Laidlaw, R.K.; Takassi, M.A.; Mattern, D.L.; Panetta, C.A. Langmuir 1990, 6, 350-357. "Monolayers and Z-type multilayers of donor-sigma-acceptor molecules with one, two, and three dodecoxy tails."