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

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A volume of 60 ml distilled water and a few drops of 2M sodium hydroxide was required to dissolve the commercially available 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. The solvent was 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. The 1S0,0-0S0,0 (HOMO-LUMO) transition was calculated to be 65 kcal/mol (2.83 eV). From the absorption onset in the red region of the spectrum, a value can be calculated for the band gap of 51.3 kcal/mol (2.23 eV) for 9.

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