Synthesis of Di-block Copolymers Containing Regioregular Poly(3-hexylthiophene) and Poly(tetrahydrofuran) by a Combination of Grignard Metathesis and Cationic Polymerizations

• Published in: Macromolecular chemistry and physics 2009-12, Vol.210 (23), p.2007-2014
• Main Authors: Alemseghed, Mussie G., Gowrisanker, Srinivas, Servello, John, Stefan, Mihaela C.
• Format: Article
• Language: English
• Subjects: Anhydrides; block copolymers; Cationic; cationic ring-opening polymerization; Copolymers; field-effect transistor; Metathesis; NMR spectroscopy; poly(tetrahydrofuran); Polymerization; regioregular poly(3-hexylthiophene); semiconducting polymers; Synthesis; Tetrahydrofuran
• ISSN: 1022-1352; 1521-3935
• DOI: 10.1002/macp.200900262

Poly(3‐hexylthiophene)‐block‐poly(tetrahydrofuran) was synthesized by cationic ring‐opening polymerization of tetrahydrofuran (THF) using a poly(3‐hexylthiophene) macroinitiator. Poly(3‐hexylthiophene) macroinitiator used for the ring‐opening polymerization of THF was synthesized by reacting the hydroxypropyl end‐group with trifluoromethanesulfonic anhydride in the presence of 2,6‐di‐tert‐butylpyridine. 1H NMR spectroscopy and SEC data confirmed the formation of the di‐block copolymers. Field‐effect mobility of poly(3‐hexylthiophene)‐block‐poly(tetrahydrofuran) was measured in a thin‐film transistor configuration and was found to be 0.009 cm2 · V−1 · s−1. Semiconducting poly(3‐hexylthiophene) has been incorporated in block copolymers with poly(tetrahydrofuran).The synthesized poly(3‐hexylthiophene)‐block‐poly(tetrahydrofuran) block copolymers have good electronic properties as confirmed by field‐effect mobility and conductivity measurements. Solvatochromic behavior of the poly(3‐hexylthiophene)‐block‐poly(tetrahydrofuran) have been observed in tetrahydrofuran/water and tetrahydrofuran/hexane mixtures.