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Structure and reactions in novel organic monolayers

Skabardonis, John Gregory
http://rave.ohiolink.edu/etdc/view?acc_num=case1054930052

Abstract Details

1990, Doctor of Philosophy, Case Western Reserve University, Chemistry.
1-Diazo-2-oxoalkanes. Long chain molecules possessing a diazomethyl ketone functionality have been used to form Langmuir films which were subsequently photolyzed with varying amounts of area available to the individual molecules. Photolysis of a diazomethyl ketone can give rise to a variety of carbene and/or ketene derived products. The properties of the films arising from these photolyses were compared to those formed from independently prepared long chain carboxylic acids, α-hydroxy ketones, and their mixtures. Creep tests and π/A isotherms of the photolyzed films indicated that very stable films were formed. Viscosity measurements were done on the films formed from the photolyses of diazomethyl ketone films. Canal viscosimeters of varying widths were used and these experiments clearly showed that film viscosity depends on the amount of area available to the molecules during the photolysis. The films displayed viscosities that were much higher than those of the possible carboxylic acid or α-hydroxy ketone products. The canal viscosimetry method has previously been used to measure the surface shear viscosity of monolayers. In those instances however, the viscosity at a single surface pressure was measured. In the modification of the method that we have used, the surface shear viscosi ty corresponding to an entire range of surface pressures can be calculated in a single experiment. (22.3.3)Propellanes. (22.3.3) propellanes containing ketone and/or hydroxyl functionalities were used to form Langmuir films whose properties were studied. A model has been proposed to allow an understanding of how these unusually shaped molecules orient themselves at the air/water interface and how they efficiently fill space in a monolayer. Tritium has been used to label a (22.3.3) propellane ketol, thus permitting the monitoring of the ratio of products formed when a Langmuir film of the material undergoes reduction with sodium borohydride. The ratio of products formed when a propellane film was reduced with varying amounts of area available to the molecules was compared to the ratios obtained when the material was reduced in the presence of micelles and in the bulk state. It was shown that the ratio of products formed from the reduction in the monolayer more closely resembles that obtained from the reduction in the bulk rather than that from the reduction in the presence of micelles.
Chaim Sukenik (Advisor)
158 p.
novel organic monolayers

Recommended Citations

Citations

  • Skabardonis, J. G. (1990). Structure and reactions in novel organic monolayers [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1054930052

    APA Style (7th edition)

  • Skabardonis, John. Structure and reactions in novel organic monolayers. 1990. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1054930052.

    MLA Style (8th edition)

  • Skabardonis, John. "Structure and reactions in novel organic monolayers." Doctoral dissertation, Case Western Reserve University, 1990. http://rave.ohiolink.edu/etdc/view?acc_num=case1054930052

    Chicago Manual of Style (17th edition)

case1054930052
538
© 1990, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.