| Abstract
| - Novel poly(quinone diimines) from anthraquinonessymmetrically disubstituted withsolubilizing ethyleneoxy or long chain alkoxy groups have beensynthesized and characterized. Thedisubstituted anthraquinones1,5-bis(2-methoxyethoxy)anthraquinone(EO1AQ), 1,5-bis(2-(2-methoxyethoxy)ethoxy)anthraquinone (EO2AQ),1,5-bis(2-(2-(2-methoxyethoxy)ethoxy)anthraquinone(EO2AQ), 1,5-bis(2-(2-2-methoxyethoxy)ethoxy)ethoxy)anthraquinone(EO3AQ), 1,5-bis(octyloxy)anthraquinone(15OOAQ),2,6-bis(octyloxy)anthraquinone (26OOAQ), and1,4-bis(octyloxy)anthraquinone (14OOAQ) weresynthesizedand condensed with aniline in the presence of titanium tetrachlorideand 1,4-diazabicyclo[2.2.2]octaneto giveN,N‘-diphenyl-1,5-bis(2-methoxyethoxy)nanthraquinone9,10-diimine (DEOnAQ, n =1−3), N,N-diphenyl-1,5-bis(octyloxy)anthraquinone 9,10-diimine(15DOOAQ), andN,N‘-diphenyl-2,6-bis(octyloxy)anthraquinone 9,10-diimine (26DOOAQ), respectively, as modelcompounds for the polymers. The relativestereochemistry of these diimines was determined by 1H NMRspectroscopy. Polycondensation of thedisubstituted anthraquinones with 4,4‘-thiodianiline (SDA) gave highmolecular weight (Mw 30 000)poly(anthraquinone diimines) and large macrocycles. Polycondensation of1,4-phenylenediamine (PDA) withEO2AQ gave high molecular weight(Mw 14 000) polyaromatic anthraquinonediimines. PDA gavemolecular weights of Mw 5000−23 000 for thebis(octyloxy)-substituted anthraquinones. Themolecularweights of polymerizations incorporating PDA are lowered due to stericinteractions of successive repeatunits and solubility constraints.
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