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Title: Structural studies on some fluorinated dithiadiazolyl radicals
Author: Haynes, D. A.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2002
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A series of partially fluorinated 1,2,3,5-dithiadizolyl aryl derivatives was prepared, in order to examine the effects of the fluorinated substituents on the solid-state structure of these molecules. 3,5-(CF3)2(C6H3CNSSN and 3-CF3C6H4CNSSN were synthesized, as well as nine isomers of CF3FC6H3CNSSN. The crystal structures of seven of these derivatives are compared, and discussed in the light of their molecular electrostatic potential maps. 3-F-4-CF3C6H3CNSSN was found to crystallize as an inclusion compound with nitrogen. The synthesis and characterisation of this inclusion compound is described, as well as the reactivity of 3-F-4-CF3C6H3CNSSN to other small molecules (Ar, CO2, O2). Several fluorinated dithiadiazolyl derivatives were synthesized in order to investigate their physical properties. EPR studies on CF3CNSSN were undertaken in order to further examine its known bistable nature. EPR studies on the novel dithiadiazolyl derivative, CF3(CF2)6CNSSN are also described, and the possibility of this radical exhibiting a liquid crystalline phase is discussed. The synthesis and solid-state structure of novel monomeric dithiadiazolyl radical, (CF3)3C6 H2CNSSN, is also described. During the course of these studies, the known dithiadiazolyl derivative, CICNSSN, was synthesized in three concomitant polymorphic forms. The solid-state structure of these compounds is described, and the competing interactions seen in the three forms are discussed in the light of the molecular electrostatic potential map and atomic partial charges of CICNSSN. A series of novel dithiatetrazocines, p-X1C6H4C2N4S2C6 H4X2 (X1, X2 = NO2, Br) was synthesized and characterized in order to study the non-linear optical properties of the unsymmetric derivative. The solid-state structures of these three derivatives are described and rationalized using their molecular electrostatic potential maps.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available