Synthesis of Functional Polyesters N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole by Anionic Ring-Opening Polymerization

Marina Markova; Artem Emel'yanov; Inna Tatarinova; Alexander Pozdnyakov

doi:10.3390/polym14204467

Synthesis of Functional Polyesters N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole by Anionic Ring-Opening Polymerization

Polymers (Basel). 2022 Oct 21;14(20):4467. doi: 10.3390/polym14204467.

Authors

Marina Markova¹, Artem Emel'yanov¹, Inna Tatarinova¹, Alexander Pozdnyakov¹

Affiliation

¹ A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.

Abstract

The functional polyethers of N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole (in up to 61% yield, M_w = 8.7-11.7 kDa) and copolymers with ethylene glycol methylglycidyl ether (M_w = 5.6-14.2 kDa) and ethylene glycol vinylglycidyl ether (M_w = 6.4-12.3 kDa) have been synthesized via anionic ring-opening polymerization in the presence of KOH without solvent. The polymerization involves the opening of the epoxy ring to deliver the linear polyethers bearing free tetrahydroindole rings and oxyethylene or vinyloxy groups in the side chain. The polyethers are soluble in ethanol, benzene, chloroform, dioxane, DMF, and DMSO. The polyethers obtained exhibit the properties of high-resistance organic semiconductors: their electrical conductivity reaches 10^-14 S/cm.

Keywords: N-(2,3-epoxypropyl)-4,5,6,7-tetrahydroindole; anionic copolymerization; anionic homopolymerization; ethylene glycol methylglycidyl ether; ethylene glycol vinylglycidyl ether.

Grants and funding

This research received no external funding.