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2-14j-1 Oxidative Polymerization of Aniline Passage of current through a solution results in oxidation (electron loss) at the anode and reduction (electron gain) at the cathode. This process is referred to as electrochemical polymerization when polymer is formed. Polyaniline [IUPAC: poly(imino-1,4-phenylene)] is obtained by the oxidative polymerization of aniline in aqueous HCl solution, either by electrochemical polymerization or by using a chemical oxidant such as ammonium persulfate, (NH4)2S2O8 [Macdiarmid et al., 1987; Mav and Zignon, 2001; Tejskal and Gilbert, 2002; Wei, 2001; Wei et al., 1989, 1990]. Polymerization proceeds by a chain polymerization mechanism, but is included in this section on conjugated polymers for convenience. Initiation involves a loss of two electrons and one proton from aniline to form a nitrenium ion (Eq. 2-223), which subsequently attacks aniline by electrophilic substitution (Eq. 2-224). Propagation proceeds in a similar manner by oxidation of the primary amine end of a growing polymer chain (Eq. 2-225) followed by electrophilic substitution (Eq. 2-226). The process has been referred to as reactivation chain polymerization to highlight the fact that the chain end formed after each addition of aniline must be reactivated to the nitrenium
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ion by oxidation and proton loss. The product formed directly from oxidative polymerization is not the neutral structure shown in Eq. 2-226. The polymer has the positively charged structure LVI, which is referred to as emeraldine salt, and it is the conducting form of polyaniline. Other forms of polyaniline can be obtained after synthesis by varying the applied voltage and pH [Sherman et al., 1994]. Polyaniline offers considerable promise for commercialization. There have been extensive studies using substituted anilines alone or in copolymerization with aniline to alter the conducting and optoelectronic properties of the polymer as well as their solubility characteristics.
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Oxidative polymerizations of thiophene and pyrrole and their derivatives are also under study to obtain polymers with conducting and optoelectronic properties [Jin et al., 2000;
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Kraft et al., 1998; Lowen and Van Dyke, 1990; Wei and Tian, 1993]. Reactions other than oxidative polymerization are also being studied for producing polyaniline and polythiophene [Kraft et al., 1998; Loewe et al., 2001]. An example is the Pd-catalyzed dehydrohalogenation between aryl dihalides and aryl primary diamines to synthesize polyanilines [Kanbara et al., 2000].
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2-14j-2 Poly(p-phenylene) One of the earliest attempts to synthesize heat-resistant polymers was the oxidative polymerization of benzene to poly(p-phenylene) [IUPAC: poly(1,4-phenylene)] (Eq. 2-227) [Jones
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and Kovacic, 1987; Kovacic and Jones, 1987]. The reaction requires the presence of both a Lewis acid catalyst and an oxidant, such as aluminum chloride and cupric chloride. Poly (p-phenylene) is of interest not only for heat resistance but also as a conducting polymer. Unfortunately, the oxidative route yields an insoluble and intractable product of low molecular weight and irregular structure (a mixture of o and p substitution). Similar results have been found for polymerization of biphenyl, p-terphenyl, and naphthalene. Alternate approaches to the poly(p-phenylene) system have been more successful [Kraft et al., 1998; Schluter, 2001]. The emphasis in these approaches has been on substituted poly(p-phenylene)s with suitable side groups that solubilize the polymer. Also of interest are chromophores as side groups to impart light-emitting properties for speci c wavelengths of light. One of the reactions successfully employed is the Suzuki coupling between arylboronic acids (or their esters) and aryl bromides (Eq. 2-228) [Hu, 2003; Schluter and Wegner, 1993]. Another useful reaction is the coupling of aryl dihalides with zinc (Eq. 2-229). These
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R (HO)2B R B(OH)2 + Br R
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reactions have been adapted for synthesis of other conjugated polyaromatic polymers, for example, poly uorenes (LVII).
2-14j-3 Poly(p-phenylene Vinylene) Poly(p-phenylene vinylene) [IUPAC: poly(1,4-phenyleneethene-1,2-diyl)] (PPV) (LVIII) is obtained by the sequence in Eq. 2-230 involving successive base- and heat-induced