219968-25-9Relevant academic research and scientific papers
Synthesis of hydroxymethyl-functionalized polyimides and the facile attachment of an organic dye utilizing bis(isocyanates) and bis(acid chloride) linkers
Wright, Michael E.,Fallis, Stephen,Guenthner, Andy J.,Baldwin, Lawrence C.
, p. 10014 - 10021 (2008/02/01)
Two new monomers were prepared of the formula 3,X-bis(4-aminophenoxy) benzenemethanol (where X = 5, 3a; X = 4, 3b) and each copolymerized with 2,2-bis(4-aminophenyl)hexafluoropropane, 6-FDA, and 6 mol % of phthalic anhydride as an end-cap to afford polyimides 4 and 5, respectively. The CH 2OH group in the polymers could be modified with excess 1,6-hexanediisocyanate to afford 100% modification of polymer 6 concomitant with formation of a pendent and reactive isocyanate group. This latter polymer was shown to react with disperse red 1 (DR-1) to produce a polyimide-supported dye (7, Tg 199°C) via formation of a urethane linkage. Treatment of the polymers 4 and 5 with excess adipoyl chloride afforded polymers 8 and 9, respectively, with a pendent acid chloride functional group. Further reaction with disperse red 1 (DR-1) in the presence of DMAP led to rapid esterification, yielding high-Tg dye-attached polyimides 11 (Tg 168°C) and 12 (Tg 175°C). Treatment of polymer 4 with sebacoyl chloride (a longer spacer) and then DR-1 in a similar manner afforded polymer 13 (T g 156°C). All dye-attached polymers showed low optical loss as measured in solution at both 1300 (～0.5 dB/cm) and 1500 nm (～1.0 dB/cm) and showed excellent thermal stability at an elevated temperature (180°C) relative to guest/host analogues.
