Synthesis and Properties of Polyacetylenes Having Pendant Carbazole Groups

Abstract

Five novel carbazole-containing polymers, i.e., poly (3,6-di-tert-butyl-9-prop-2-ynylcarbazole) [poly(t-Bu2CzPr)], poly(9-but-2-ynylcarbazole) [poly(CzBu)], poly (3,6-di-tert-butyl-9-but-2-ynylcarbazole) [poly(t-Bu2CzBu)], poly(9-(4-ethynylphenyl)carbazole) [poly(p-CzPA)], and poly(9-(4-prop-1-ynylphenyl)carbazole) [poly(p-CzPPr)] were synthesized by the polymerization of the corresponding carbazolecontaining acetylene monomers using [(norbornadiene)RhCl]2-Et3N, WCl6, MoCl5, TaCl5, and NbCl5 in conjunction with Sn, Bi, Sb, and Si cocatalysts and W(CO)6-hν/CCl4 catalysts. The UV-vis absorption band edge wavelengths of poly(t-Bu2CzPr) and poly(p-CzPA) were longer than those of the corresponding polymers substituted by methyl group at the main chain, poly(t-Bu2CzBu) and poly(p-CzPPr), respectively. The band edge wavelengths of phenylene-spacer-containing polymers, poly(p-CzPA) and poly(p-CzPPr), were longer than those of methylene-spacer-containing polymers, poly(t-Bu2CzPr) and poly(t-Bu2CzBu), respectively. Poly(p-CzPA) obtained by WCl6-n-Bu4Sn-catalyzed polymerization exhibited UV-vis absorption apparently at a longer wavelength than the MoCl5-n-Bu4Sn-based counterpart did. Poly-(t-Bu2CzPr) showed photoconductivity. The temperatures for 5% weight loss of the polymers were around 300-350 °C under air.

Low-potential electrochemical polymerization of carbazole and its alkyl derivatives

“…In the case of carbazole-based conjugated polymers, all previous studies were devoted to 3, 6-linked N-substituted carbazole units [6][7][8][9]. As reported for many other conjugated polymers, the synthesis of well-defined carbazole polymer has been sustained by the clever utilization of a variety of synthetic tools, such as Kumada, Stille, Yamamoto, Suzuki couplings, etc.…”

Synthesis and properties of polyacetylenes carrying N-phenylcarbazole and triphenylamine moieties

“…1 H NMR spectra of 1, poly(1), 2, and poly(2). Polymer samples from run 1 in Table 1 and run 1 in Table 2. good compared to that of poly(N-ethynylcarbazole) [8] and poly [N-(4-ethynylphenyl)carbazole] reported previously [14]; the latter two polymers obtained with [(nbd)RhCl] 2 eEt 3 N catalyst are insoluble in common organic solvents including toluene, CHCl 3 and THF. Thus, it is clear that the substitution position greatly affects the solubility of the polymers.…”

Electro-optical properties of poly(2-ethynyl-N-propargylpyridinium compound) with different counter ions

“…Thus it was difficult for practical applications to opto-electronic devices as an active material. To overcome these problems of PA itself, various types of conjugated polymers including poly(aromatic heterocycle)s were prepared and characterized [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19].…”

“…Especially, the substituted PAs have been prepared by the linear polymerization of the corresponding 1567 acetylene monomers by various catalyst systems [8][9][10][11][12][13][14][15][16][17][18][19]. The polymers having a conjugated backbone are expected to show unique properties such as electrical conductivity, paramagnetism, migration and transfer of energy, color, and chemical reactivity and complex formation ability [9].…”