Feld Group Research

Research

The Feld Group

Research Interests

Organic Synthesis

Haplomyrtin is a member of the 1-arylnaphthalene lignan lactone series of natural products. They have attracted considerable attention due to their widespread occurrence in nature and the diverse range of their biological activity. The synthesis of this compound presents several challenges. Standard synthetic procedures have provided several precursors of Haplomyrtin. Thsi system appears to be a candidate for solid phase synthetic techniques as well as combinatorial approaches.

Cyclopentadienones are starting materials for a variety of new materials for NLO applications, OLED polymers and polycyclic aromatic hydrocarbons. Carboxylated cyclopentadienones can be converted into terephthalic ester derivatives, which can be converted into indeno[2,1-c]fluorene derivatives in a few steps. Terephthalates can be precursors for bis(chloromethyl)benzenes that can be used as monomers in the preparation of substituted poly(phenylene vinylene)s.

Monomer/Polymer Synthesis

Conducting and electronically active organic materials offer many advantages over traditional metallic systems - light weight, easy processing, larger variety of forms and wider range of activity. Effective and low cost routes to highly pure monomers that are specifically required for the synthesis of poly(phenylene vinylene) (a conductive polymer), PBT (a structural and electronically active material), polyimides (molecular composite components), and non-linear optical (NLO) materials (fiber optic and photonic device components) are of special interest. The determination of optimum polymerization and processing conditions as well as the synthesis of related systems are being investigated.

Thermally stable and potentially ordered polymers such as polyimides and poly(benzothiazoles) have potential importance as structural materials in the aircraft and automotive industries and as active components in the electronics industry. The determination of structure-property relationships for these polymer systems is an important research area for the "tailoring" of materials for specific applications. The synthesis of these polymers requires careful planning and execution of accepted polymerization techniques and the development of new techniques that account for individual monomer properties. Bifunctional monomers are unique in that they contain both functional groups necessary for the formation of a polymer chain by a condensation reaction. They offer significant synthetic challenges because of the need to have two mutually reactive groups in the same molecule.

Theses Published by the Feld Group 1977 -

1. “Phenylated Bifunctional Monomers,” Lucia Serico, 1977.

2. “Evaluation of Poly(p-vinyltrifluoroacetophenone) and Some Derivatives as Stationary Phases For Gas Chromatographic Analysis,” David M. Pinson, 1980.

3. “Reaction of Poly(Acrylic acid), Poly(Sodium Acrylate) and Selected Carboxylate-Containing Resins with Aqueous Solutions Containing the Uranyl Ion,” S. Tsuji, 1981 (Codirected with C.E. Carraher).

4. “The Effects on Rigidity as a Function of Para-Ethynylphenoxy Linkage in an Acetylene Terminated Thermosetting System,” J. Gamble, 1981 (Codirected with F.E. Arnold, Materials Laboratory, WPAFB, OH).

5. “Polyimides Containing Oxyethylene Units,” B. Ramalingam, 1981.

6. “Phenylated Poly(Xylylidenes),” A. Ganesan, 1982.

7. “The Synthesis and Selected Reactions of a Series of a,w-Bis(p-Bromophenoxy)alkanes,” S. Babirad, 1982.

8. “Synthesis of 5- and 6-(1-Hydroxy-2-aminoethyl)-1-ethoxy-1,2,3-Benzotriazole,” D. Evans, 1982.

9. “The Control of Acetylene Terminated Resin Length Via a Low Cost Ullmann Ether Synthesis,” M. Unroe, 1982 (Codirected with F.E. Arnold, Materials Laboratory, WPAFB, OH).

10. “The Synthesis and Characterization of Selected Bis(propynoyloxy)aromatics,” J. Wehler, 1983.

11. “Synthesis and Characterization of Bis(3-nitro-4-aryloxyphenyl) and Bis(3-amino-4-aryloxyphenyl) Sulfones,” S. M. Andrews, 1984.

12. “High Molecular Weight Bis-Phenol Based Acetylene Terminated Resins,” J. S. Wallace, 1984 (Codirected with F.E. Arnold, Materials Laboratory, WPAFB, OH).

13. “A Study of the Synthesis of 3-Phenoxy- and 3,6-Diphenoxypyromellitic Dianhydride and A Preliminary Polyimide Investigation,” D. Brandelik, 1985.

14. “A Study of the Synthesis of Ethyl Chlorosubstituted Benzotriazoloxyacetates,” T. Dang, 1986.

15. “Phenylated Monomer Synthesis: Trans-2,3-Diphenyl-2-butenedial and 3,6-Diphenyl-pyromellitic Dianhydride,” S. Liang, 1986.

16. “The Synthesis and Polymerization of 1,2-Bis(4-aminophenoxy)propane,” S. Tjugito, 1987.

17. “End Group Analysis of Hexafluoro-Vinylidene Fluoride Copolymers,” W.J. Donahue, 1987 (Selected Studies).

18. “A Computational Study of The tensile and Compressive Properties of Ordered Polymers Via the Austin Model 1 (AM1) Semiempirical Molecular Orbital Method,” S.G. Wierschke, 1988 (Codirected with I.J. Goldfarb, Materials Laboratory, WPAFB, OH).

19. “Polyimides Based on Nitrogen Linked Diamines and Polybenzothiazoles from A-B Monomer,” T.B. Le, 1988.

20. “Polyimides Derived From Alkyl-Substituted Oxyethylene Linked Diamines,” M. Gurjar, 1988.

21. “The Synthesis of Rigid-Rod Poly(benzothiazole)s Containing Orthogonal Phenyl Pendents,” Y. Chang, 1988.

22. “Polyimides Containing Naphthalene And Oxyethylene Units,” K. Paulvannan, August, 1989.

23. “The Synthesis of Bismaleimides Containing Oxyethylene Linkages,” J.D.Peak, August, 1989.

24. “The Synthesis and Characterization of Novel Imide Model Compounds,” D.L. Routzahn, August, 1990 (Codirected with L.S. Tan, Materials Laboratory, WPAFB, OH).

25. “The Synthesis of Poly(ether ether ketone)s Containing Oxyethylene Units From An AB Monomer,” B. Kirk, June 1991.

26. “A Facile Synthesis of 3,4-Dialkoxythiophenes,” M.J. Coffey, August, 1991.

27. “The Synthesis of Poly(Ether Ether Ketone)s from Bis(fluorobenzophenone) Monomers Containing Oxyethylene Linkages,” B. Patel, June, 1992.

28. “The Synthesis of Poly(Ether Ether Ketone)s Containing Oxyethylene Units,” M. Patel, September, 1992.

29. “The Synthesis and Characterization of Selected Fluorinated-Phenylated Poly(imide)s,” D. Drake, March, 1993.

30. “Novel Hexafluoropropane Containing Monomers and Polymers,” J. Truini-Winzeler, June, 1993.

31. “Synthesis of Trifluoromethyl Containing PBZ Polymers,” R. Jennings, August, 1993.

32. “Synthesis and Evaluation of the Second Order Polarizabilities of Novel Benzimidazoles Using Solvatochromism,” S. Shanbag, August, 1993.

33. “Polymeric Cyanine Dyes Based Upon 3H-Indole Monomers,” S. Gabbard, March 1994.

34. “Conformer Analysis Study of 1,2-Dihalotetrafluoroethanes by Gas Chromatography /Fourier Transform Infrared Spectroscopy (GC/FTIR),” M. Roselius, June 1994. (Codirected with J.C. Liang and H. Paige, Materials Laboratory, WPAFB, OH)

35. “An Isothermal Aging Study of Poly(Ether Ether Ketone)s Containing Oxyalkylene Linkages,” E. Luo, August, 1994

36. “The Synthesis of Monomeric Precursors of Molecular Switches,” C. Brown, August, 1994.

37. “The Synthesis of Poly(Ether Ether Ketone)s Derived from 1,1-Bis(4-hydroxyphenyl)-1-phenyl-2,2,3,3,4,4,4-heptafluorobutane,” J. Peterman, August, 1994.

38. “The Synthesis of Polybenzoxazoles Containing Phosphine Oxide and Hexafluoroisopropylidene Linkages,” N. Theising, August, 1995.

39. “Conjugated Polymer Systems and Synthesis of Phenylated Aromatic Monomers,” T. Nijakowski, March, 1996.

40. “Total Synthesis of the Arylnaphthalene Lignan, Haplomyrtin,” T. Gilmore, June, 1996.

41. “31P Nuclear Magnetic Resonance Studies of Energy Transduction and Phosphorylation of the Aerobic Photosynthetic Rhizobium, BTAi 1,” R. Ingham, August, 1996.

42. “Synthesis and Characterization of High Birefringence Tolane Liquid Crystal Siloxanes,” C. McHugh, August, 1996.

43. “Tetraphenylnaphthalene Derivatives for Nonlinear Optical Property Evaluation,” D. Stitzel, December, 1996.

44. “Synthesis of a Series of Poly(para-phenylene) Compounds for Nonlinear Optical Property Evaluation,” R. Haaga, June, 1998.

45. “The Synthesis of 5,8-Dioxo-5,8-dihydroindeno[2,1-c]fluorenes,” E. Lorge, June, 1998.

46. “The Wittig Synthesis of Poly(hexyldiphenylphenylene vinylene),” M. Cheek, August, 1998.

47. “Synthesis of Soluble Poly(p-Phenylene Vinylenes) and Selected Enhancements in the Synthesis of Haplomyrtin,” G. Schaaf, June, 1999.

48. “The Synthesis of Brominated 5,8-Dioxo-5,8-dihydroindeno[2,1-c]fluorene and Derivatives,” Michelle Torres, June, 1999.

49. “Synthesis of Benzoxazoles Containing Allyl Crosslinking Sites via Claisen Rearrangements,” Leslie Hutson, August, 1999.

50. “Studies Directed at the Synthesis of Trialkoxysilyl Substituted NLO Chromophores Ida. Kuhr,” June, 2000.

51. “The Functionalization of Thermally Stable Third-Order NLO Chromophores,“ James Sawyer, June 2001.

52. “The Synthesis of Bromoethoxy and Vinylbenzyloxy Substituted NLO Chromophores,” Mike Matuszewski, March 2002

53. “Selected Synthetic Studies of NLO p-Bridges and Thermally Stable Monomers,” Stacey Fauley, June 2002

54. "Synthesis of Disubstituted 5,8-Dioxo-5,8-dihydroindeno[2,1-c]fluorenes," Rachel Smith, June 2003

55. "Synthesis of a Novel Polybenzoxazole Containing the Triphenylphosphine Oxide Functionality," Steve Sims, June 2003

56. "Synthesis of An AB2 PBO Monomer Precursor: 5-(6-hydroxy-5-nitrobenzoxazol-2-yl)isophthalic Acid," Xiao Cui, August 2004.

57. "Synthesis of Poly(ether ether ketone)s Containing a Tertiary Amine Subunit," Kathryn M. McGinty, August 2004.

58. "Synthesis of Phenylated Poly(Aryleneether)s: Phenylated Poly(Ether Ether Ketone Ketones," Tina Dancevic, August 2005.

59. "Challenging Synthesis of Arylnaphthalene Lignans," Shingirai Chirisa, March, 2006.

60. "Hydrogen Storage and the Synthesis of 5,8-Dihydroindeno[2,1-c]fluorenes," Kirby Underwood, June, 2006.

61. "p-Terphenyl Rigid-Rod Polymers with Benzothiazole Pendents for Compressive Strength Applications," Joeseph Shumaker, June, 2006.

62. "Synthesis and Electrical Properties of Fluorenyl Polyesters Incorporating Diamond Fragments," Kevin Wiacek, June, 2007.