1,3,5-TRIIODOBENZENE

The Uses of 1,3,5-TRIIODOBENZENE

1,3,5-Triiodobenzene is used in the synthesis of conjugated microporous polymers through cationic cyclization polymerization. It also can be used in optical materials.

Synthesis

1,3,5-Triiodobenzene was synthesized by reacting 2,4,6-triiodoaniline with NaNO2 in the presence of copper(I) oxide.
Experimental procedure: Finely ground NaNO2 (1.95 g, 0.028 mol) was slowly added with stirring to sulfuric acid (3.5 mL). Then a solution of 2,4,6-triiodoaniline(2.90 g, 6.16 mmol) in glacial AcOH (130 mL) was added dropwise with stirring and cooling at such a rate that the temperature of the reaction mixture was kept below 20 °C. Following addition of the amine, the reaction mixture was stirred at ≈20 °C for about 30 min. The resulting solution of the diazonium salt was added dropwise to a suspension of copper(I) oxide (2.52 g) in dry ethanol (70 mL) with vigorous stirring over 15 min. The reaction mixture was brought to boiling and stirred for 30 min until elimination of nitrogen ceased. Then the mixture was cooled, kept for one day, poured into ice water (300 mL), and extracted with benzene (3×50 mL). The benzene extracts were dried with anhydrous Na2SO4 and the solvent was distilled off in vacuo. The residue was repeatedly recrystallized from benzene. The yield was 2.01 g (84%), m.p. 182 °C (cf. lit. data11: m.p. 183 °C). 1H NMR (CDCl3), δ: 8.02 (s, 3 H, CH). 13C NMR (CDCl3), δ: 79; 128.