Department of Chemistry and Biochemistry

We are studying 2,2'-bithiophenes and 2,2’:5’,2”-terthiophenes with various substituents on the 3-, 3’- and 3”- positions to examine factors involved in producing completely, or nearly completely, planar systems. We are examining properties such as thiophene-thiophene dihedral angles and barriers to rotation, along with any interactions of substituents with the sulfur atoms in adjacent rings, by both theoretical calculations and single crystal X-ray crystallography, after synthesis of these molecules. We have shown theoretically, using ab-initio quantum mechanical calculations, that certain functional groups will stabilize planar (but somewhat distorted) or nearly planar structures because of Coulombic stabilization of polar resonance forms. This stabilization causes some distortion of the molecules, reduced dihedral angles and low rotation barriers. We have also demonstrated theoretically that certain other substituents allow the bithiophene to be completely planar, even with head-to-head substitution. Synthetic routes to these distorted but planar bithiophenes and, therefore, to completely planar, conjugated polythiophenes are being examined. Thus, the carbonyl oxygen has been shown to have a considerable intramolecular Coulombic attraction to a thiophene sulfur atom. When the oxygen atom is replaced by an extremely electronegative fluorine atom, there seems to be essentially no intramolecular attraction between the fluorine and sulfur atoms. However, there is now an intermolecular attraction between these atoms and this considerably alters the morphology of the crystal structure. We are studying the scope of these interactions, which can give rise to self-assembly, in other thiophene and benzothiophene systems as well as in sulfur containing heterocyclic systems where the sulfur has considerable positive charge character, similar to the thiophenes

Representative Publications

Pomerantz, M.; Gu, X.; Zhang, S. X. "Poly(2-decylthieno[3,4-b]thiophene-4,6-diyl). A New Low Band Gap Conducting Polymer," Macromolecules, 2001, 34, 1817.

Pomerantz, M.; Amarasekara, A. S.; Dias, H. V. R., "Synthesis and Solid State Structures of Dimethyl 2,2'-Bithiophenedicarboxylates", Journal of Organic Chemistry 2002, 67, 6931-6937.

Pomerantz, M. “Planar 2,2’-bithiophenes with 3,3’- and 3,3’,4,4’-Substituents. A Computational Study,” Tetrahedron Letters 2003, 44, 1563-1565.

Pomerantz, M.; Amarasekara, A. S. "Studies of Planar Poly(3,4-disubstituted-thiophenes)," Synthetic Metals 2003, 135-136, 245-246.

Amarasekara, A. S.; Pomerantz, M. “Synthesis and Study of Head-to-Tail Regioregular Poly(alkyl thiophene-3-carboxylates),” Synthesis 2003, 2255-2258.

Pomerantz, M.; Liu, L.; Zhang, X. “Synthesis and Study of Poly[3-(6-substitutedhexyl)thiophenes] and Poly[3-(12-substituteddodecyl)thiophenes] Containing Halogen and Sulfur Substituents,” Arkivoc 2003 (xii), 119-137.

Purvinis, G.; Priambodo, P.; Zhou, M.; Pomerantz, M.; Maldonado, T.; Magnusson, R. “Second-harmonic generation in resonant waveguide gratings incorporating ionic self-assembled monolayer polymer films,” Optics Letters, 2004, 29, 1108-1110.

Rasmussen, S. C. ; Pomerantz, M. “Low Bandgap Conducting Polymers,” in Handbook of Conducting Polymers, 3rd Edition; Skotheim, T. A.; Reynolds, J. R. Eds.; CRC Press: Boca Raton, FL, 2007; “Conjugated Polymers, Theory, Synthesis, Properties, and Characterization,” Chapter 12, pp 421-462.

Pomerantz, M.; Turkman, N. “A Facile and Improved Synthesis of 3-Fluorothiophene,” Synthesis 2008, 2333-2336.

Turkman, N.; An, L.; Pomerantz, M. “One-Pot Desulfurative-Fluorination-Bromination. Synthesis of 2,5-Dibromo-3-(1,1-difluoroalkyl)thiophenes,” Organic Letters 2010, 12, 4428-4430.

Patent

Magnusson, R.; Maldonado, T. A.; Priambodo, P.; Zhou, M.; Purvinis, G.; Pomerantz, M. “Nonlinear Optical Guided Mode Resonance Filter” United States Patent No. 7,218,817, issued May 15, 2007.

B.S. City College of New York (1959)

M.S. Yale University (1961)

Ph.D. Yale University (1964)

N.S.F. Postdoctoral Fellow:
The University of Wisconsin (1963-1964)

EDUCATION

Ph.D Yale University, 1964

M.S. Yale University, 1961

B.S. City College of New York, 1959

EXPERIENCE

University of Texas at Arlington, Arlington, TX

Professor of Chemistry, 1976 to present.

Interim Associate Chair, Department of Chemistry and Biochemistry, 8/2004-8/2005.

Director, Center for Advanced Polymer Research, 1991-present, co-director, 1988-1991.

National Science Foundation, Arlington, VA, Program Officer, Chemistry Division, 8/2005-8/2007

Ben-Gurion University of the Negev, Beer Sheva, Israel, Visiting Professor, Summer 1981, 1985.

Yeshiva University, New York, NY

Chairman, Department of Chemistry, Belfer Graduate School of Science, 1973-1976; Acting

Chairman, 1971-1972; Professor, 1974-1976; Associate Professor, 1969-1974.

Columbia University, New York, NY, Visiting Professor, Fall 1975, 1974, Summer 1970-1975.

University of Wisconsin, Madison, WI, Visiting Associate Professor, Fall 1972.

Case Institute of Technology/Case Western Reserve University, Cleveland, OH

Assistant Professor, 1964-1969 (Awarded tenure but turned it down).

University of Wisconsin, Madison, WI, National Science Foundation Postdoctoral Fellow, 1963-1964.

New York University, New York, NY, Research Assistant, Summer, 1959.

AREAS OF EXPERTISE

Monomer and Polymer Synthesis, Physical and Synthetic Organic Chemistry, Conducting, Light Emitting and

Second Order Nonlinear Optical Polymers, Ionic Self Assembly, NMR Spectroscopy.

Alfred P. Sloan Foundation Fellow (1971-1976)

W. T. Doherty Award, D/FW Section of the American Chemical Society (1997)

University Distinguished Record of Research Award (1997)

Wilfred T. Doherty Award of the Dallas-Fort Worth Section of the American Chemical Society (1997)

University of Texas at Arlington Distinguished Record of Research Award (1997)

Alfred P. Sloan Foundation Research Fellow (1971-1976)

NSF Predoctoral and Honorary Sterling Fellow (1962-1963)

Leeds and Northrup Fellow (1960-1962)

Woodrow Wilson Fellow (1959-1960)

Elected to Phi Beta Kappa (1959)

CCNY: Ward Medals in Chemistry and German, Revlon Foundation Scholarship.

Listed in: Who's Who in America, Who's Who in the World, Who's Who in Science and Engineering, Who’s Who in the South and Southwest.