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used for this purpose is the nucleophilic substitution on a phthalocyanine dichloride by a diphenol reactant (Eq. 2-237) [Snow and Grif th, 1988].
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Polymerization without Reaction at Metal Bond
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An alternate synthetic approach to organometallic polymers is to perform reactions where the metal atom is not the reaction site. An example is a polyesteri cation between an organometallic monomer containing two carboxyl groups and a diol (Eq. 2-238). Reaction of the diacid with a diamine would yield an organometallic polymer via polyamidation. A wide range of other reactions covered in this chapter can be used to synthesize organometallic polymers.
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Polysilanes are polymers in which there is catenation of silicon, that is, where silicon atoms are bonded to each other in a continuous manner. Synthesis of polysilanes involves the Wurtz coupling of diorganodichlorosilanes with sodium metal (Eq. 2-239) [Baldus and Jansen, 1997; Corriu, 2000; Manners, 1996; Miller and Michl, 1989; West, 1986; West and Maxka,
R Si R
RR SiCl2
1988; Yajima et al., 1978]. The reaction is typically carried out in a hydrocarbon solvent such as toluene, xylene, or octane at temperatures above 100 C. Polymerization can be achieved at ambient temperature in the presence of ultrasound, which produces high temperature and
pressures locally for short bursts [Kim and Matyjaszewski, 1988]. The mechanism for this reaction is not established, but most evidence indicates polymerization is a complex process involving some combination of radical, anionic, and silylene (the Si analog of carbene) intermediates [Gauthier and Worsfold, 1989; Matyjaszewski et al., 1988]. Furthermore, although included in this chapter, the polymerization is probably a chain reaction. It is included here because of its technological importance in complementing the sol gel process for producing ceramics. The corresponding polystannanes and polygermanes (Sn and Ge in place of Si) have also been synthesized by the Wurtz coupling reaction. Polysilanes have been synthesized with various combinations of alkyl and aryl substituents. Polysilanes, such as polydimethylsilane or polydiphenylsilane, with symmetric substitution are highly crystalline and show little or no solubility in a range of organic solvents. (The IUPAC names of the two polymers are poly(dimethylsilanediyl) and poly(diphenylsilanediyl), respectively. They have also been referred to as polydimethylsilylene and polydiphenylsilylene.) Crystallinity is decreased and solubility increased when R and R0 are different or for copolymers derived from two different symmetrically substituted dichlorosilanes. There is considerable interest in polysilanes from several viewpoints. Many of the interesting properties of polysilanes result from the relative ease of delocalization of the electrons in the catenated Si s-bonds as evidenced by the strong ultraviolet absorption at Si 300 400 nm. Polysilanes undergo photolytic radical cleavage with a high quantum yield and offer potential as radical initiators and positive photoresists. (In a positive photoresist application, the portions of a polymer not protected by a mask are degraded by irradiation and then dissolved by solvent or photovolatilized.) Polysilanes also offer potential as semiconductor, photoconductor and nonlinear optical materials. The greatest interest in polysilanes is probably in their use as preceramic polymers. The normal powder metallurgy techniques for processing ceramic materials limits the complexity of the objects that can be produced. Polysilane chemistry offers an alternate with good potential for making a variety of objects, including ber. Thermolysis of a polysilane in an inert atmosphere at 450 C yields a polycarbosilane through a complex rearrangement process. For example, poly(dimethylsilanediyl) yields poly(methylsilanediylmethylene) (LXI) (Eq. 2-240). A soluble portion of the polycarbosilane is isolated by fractional precipitation from n-hexane and used as a ceramic precursor. The soluble polycarbosilane can be formed into objects (including bers) and then pyrolyzed at 1200 C to yield the corresponding crystaline b-silicon carbide ceramic objects. Other organometallic polymers are being studied for use as precursor polymers for other ceramic systems, such as polysilazanes for silicon nitride [Baldus and Jansen, 1997; Baney and Chandra, 1988].