Diaminostilbenedisulfonic acid → 4,4'-Diiminostilbene-2,2'-disulfonic acid thiophene

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Reaction Steps

Distilled water (60 ml) and a few drops of 2M sodium hydroxide was required to dissolve 4,4′-diaminostilbene-2,2′-disulfonic acid (155 mg, 0.41 mmol). After the addition of 40 ml THF, 2,5-thiophene dicarboxaldehyde (58 mg, 0.42 mmol) was added along with a catalytic amount of benzyltriethyl ammonium chloride. The red coloured solution was stirred at room temperature for two days and the solvent removed under reduced pressure to afford the polymer as a red solid that was recrystallized from ethanol. λmax (water): 305 and 338 nm. Mw=148 094, PDI=2.3, DP==286. 1H-NMR (200 MHz, [D] DMSO): δ=8.92 (br, s, 2H), 8.21 (br, s, 2H), 7.80 (br, s, 6H), 7.39 (br, s, 2H). Anal. cald. C20H12O6N2S3Na2.7.2H2O: C, 37.06; H, 4.11; N, 4.32, S, 14.84 found C, 37.27, H, 3.90, N, 4.28, S, 14.62.

Provenance & Evidence