Single-Step Preparation of Polythiophene Bearing Branched Chains by Dual Initiation Polymerization

Jae Keun Hong; Yong Seok Kim; Wonseok Cho; Jung Hyun Kim

Macromolecular Research, Vol.25, No.3, 243-248, March, 2017

DOI10.1007/s13233-017-5028-6 Export Citation

Single-Step Preparation of Polythiophene Bearing Branched Chains by Dual Initiation Polymerization

Jae Keun Hong, Yong Seok Kim¹, Wonseok Cho, and Jung Hyun Kim^†

Department of Chemical and Biomolecular Engineering, Yonsei University, 50 Yonsei-ro, Seodaemoon-Gu, Seoul 03722, Korea
¹Materials Science and Engineering, University of Wisconsin-Milwaukee, 3200 N Cramer St., Milwaukee, WI, 53211, USA

E-mail:

A facile approach for the single-step preparation of branched polythiophenes using a copper(II) catalyst via a dual initiation polymerization process is reported. The synthetic route of dual initiation polymerization involves both oxidative polymerization and metal-catalyzed radical polymerization. In this process, two kinds of polymerization can be performed concurrently as a one-pot reaction using a Cu2+/Cu+ switchable catalytic system. Differential scanning calorimetry and photoluminescence studies confirmed the formation of the π-conjugated polymer structure. Our results provide new insights on the various grafting of copolymers with polythiophene copolymers and functional branched chains using a single-step process. This process could lead the way for enhanced processability towards novel functionalized π-conjugated polymers.

Keywords:dual initiation;graft copolymer;polythiophene

[References]

Coakley KM, McGehee MD, Chem. Mater., 16, 4533 (2004)
Gunes S, Neugebauer H, Sariciftci NS, Chem. Rev., 107(4), 1324 (2007)
Li G, Shrotriya V, Huang JS, Yao Y, Moriarty T, Emery K, Yang Y, Nat. Mater., 4(11), 864 (2005)
McQuade DT, Pullen AE, Swager TM, Chem. Rev., 100(7), 2537 (2000)
Chen L, McBranch DW, Wang HL, Helgeson R, Wudl F, Whitten DG, Proc. Natl. Acad. Sci., 96, 12287 (1999)
Ho HA, Leclerc M, J. Am. Chem. Soc., 126(5), 1384 (2004)
Pei QB, Yu G, Zhang C, Yang Y, Heeger AJ, Science, 269(5227), 1086 (1995)
Sirringhaus H, Wilson R, Friend R, Inbasekaran M, Wu W, Woo E, Grell M, Bradley D, Appl. Phys. Lett., 77, 406 (2000)
Nyholm L, Nystrom G, Mihranyan A, Stromme M, Adv. Mater., 23(33), 3751 (2011)
Skotheim TA, Reynolds J, Conjugated Polymers: Theory, Synthesis, Properties, and Characterization, CRC Press, Boca Raton, 2006.
Ballauff M, Angew. Chem.-Int. Edit., 28, 253 (1989)
Lin JWP, Dudek LP, J. Polym. Sci. A: Polym. Chem., 18, 2869 (1980)
Yamamoto T, Sanechika K, Yamamoto A, J. Polym. Sci., Polym. Lett. Ed., 18, 9 (1980)
Kobayashi M, Chen J, Chung TC, Moraes F, Heeger A, Wudl F, Synth. Met., 9, 77 (1984)
Kaneto K, Yoshino K, Inuishi Y, Solid State Commun., 46, 389 (1983)
Wei Y, Chan CC, Tian J, Jang GW, Hsueh KF, Chem. Mater., 3, 888 (1991)
Niemi VM, Knuuttila P, Osterholm JE, Korvola J, Polymer, 33, 1559 (1992)
Olinga T, Francois B, Synth. Met., 69, 297 (1995)
Andersson MR, Selse D, Berggren M, Jarvinen H, Hjertberg T, Inganas O, Wennerstrom O, Osterholm JE, Macromolecules, 27(22), 6503 (1994)
Kim YS, Lee HJ, Govindaiah P, Son W, Koh WG, Cheong IW, Kim JH, Materials, 7, 195 (2014)
Kim YS, Lee SM, Govindaiah P, Lee SJ, Lee SH, Kim JH, Cheong IW, Synth. Met., 175, 56 (2013)
Park JW, Lee DH, Chung DS, Kang DM, Kim YH, Park CE, Kwon SK, Macromolecules, 43(5), 2118 (2010)
Garcia G, Timon V, Hernandez-Laguna A, Navarro A, Fernandez-Gomez M, Phys. Chem. Chem. Phys., 13, 10091 (2011)
Balamurugan SS, Bantchev GB, Yang Y, McCarley RL, Angew. Chem.-Int. Edit., 117, 4950 (2005)
Das S, Chatterjee DP, Samanta S, Nandi AK, RSC Adv., 3, 17540 (2013)
Wang MF, Zou S, Guerin G, Shen L, Deng KQ, Jones M, Walker GC, Scholes GD, Winnik MA, Macromolecules, 41(19), 6993 (2008)
Govindaiah P, Kim YS, Hong JK, Kim JH, Cheong IW, RSC Adv., 5, 93717 (2015)
Das S, Samanta S, Chatterjee DP, Nandi AK, J. Polym. Sci. A: Polym. Chem., 51(6), 1417 (2013)
Ghosh R, Das S, Chatterjee DP, Nandi AK, Langmuir, 32(33), 8413 (2016)
Bernaerts KV, Du Prez FE, Prog. Polym. Sci, 31, 671 (2006)
Wang Z, Wang Y, Xu D, Kong ESW, Zhang Y, Synth. Met., 160, 921 (2010)
Wang CC, Tsai H, Shih HH, Jeon S, Xu Z, Williams D, Iyer S, Sanchez TC, Wang L, Cotlet M, ACS Appl. Mater. Interfaces, 2, 738 (2010)

[Related Articles]

[1] Coakley KM, McGehee MD, Chem. Mater., 16, 4533 (2004)

[2] Gunes S, Neugebauer H, Sariciftci NS, Chem. Rev., 107(4), 1324 (2007)

[3] Li G, Shrotriya V, Huang JS, Yao Y, Moriarty T, Emery K, Yang Y, Nat. Mater., 4(11), 864 (2005)

[4] McQuade DT, Pullen AE, Swager TM, Chem. Rev., 100(7), 2537 (2000)

[5] Chen L, McBranch DW, Wang HL, Helgeson R, Wudl F, Whitten DG, Proc. Natl. Acad. Sci., 96, 12287 (1999)

[6] Ho HA, Leclerc M, J. Am. Chem. Soc., 126(5), 1384 (2004)

[7] Pei QB, Yu G, Zhang C, Yang Y, Heeger AJ, Science, 269(5227), 1086 (1995)

[8] Sirringhaus H, Wilson R, Friend R, Inbasekaran M, Wu W, Woo E, Grell M, Bradley D, Appl. Phys. Lett., 77, 406 (2000)

[9] Nyholm L, Nystrom G, Mihranyan A, Stromme M, Adv. Mater., 23(33), 3751 (2011)

[10] Skotheim TA, Reynolds J, Conjugated Polymers: Theory, Synthesis, Properties, and Characterization, CRC Press, Boca Raton, 2006.

[11] Ballauff M, Angew. Chem.-Int. Edit., 28, 253 (1989)

[12] Lin JWP, Dudek LP, J. Polym. Sci. A: Polym. Chem., 18, 2869 (1980)

[13] Yamamoto T, Sanechika K, Yamamoto A, J. Polym. Sci., Polym. Lett. Ed., 18, 9 (1980)

[14] Kobayashi M, Chen J, Chung TC, Moraes F, Heeger A, Wudl F, Synth. Met., 9, 77 (1984)

[15] Kaneto K, Yoshino K, Inuishi Y, Solid State Commun., 46, 389 (1983)

[16] Wei Y, Chan CC, Tian J, Jang GW, Hsueh KF, Chem. Mater., 3, 888 (1991)

[17] Niemi VM, Knuuttila P, Osterholm JE, Korvola J, Polymer, 33, 1559 (1992)

[18] Olinga T, Francois B, Synth. Met., 69, 297 (1995)

[19] Andersson MR, Selse D, Berggren M, Jarvinen H, Hjertberg T, Inganas O, Wennerstrom O, Osterholm JE, Macromolecules, 27(22), 6503 (1994)

[20] Kim YS, Lee HJ, Govindaiah P, Son W, Koh WG, Cheong IW, Kim JH, Materials, 7, 195 (2014)

[21] Kim YS, Lee SM, Govindaiah P, Lee SJ, Lee SH, Kim JH, Cheong IW, Synth. Met., 175, 56 (2013)

[22] Park JW, Lee DH, Chung DS, Kang DM, Kim YH, Park CE, Kwon SK, Macromolecules, 43(5), 2118 (2010)

[23] Garcia G, Timon V, Hernandez-Laguna A, Navarro A, Fernandez-Gomez M, Phys. Chem. Chem. Phys., 13, 10091 (2011)

[24] Balamurugan SS, Bantchev GB, Yang Y, McCarley RL, Angew. Chem.-Int. Edit., 117, 4950 (2005)

[25] Das S, Chatterjee DP, Samanta S, Nandi AK, RSC Adv., 3, 17540 (2013)

[26] Wang MF, Zou S, Guerin G, Shen L, Deng KQ, Jones M, Walker GC, Scholes GD, Winnik MA, Macromolecules, 41(19), 6993 (2008)

[27] Govindaiah P, Kim YS, Hong JK, Kim JH, Cheong IW, RSC Adv., 5, 93717 (2015)

[28] Das S, Samanta S, Chatterjee DP, Nandi AK, J. Polym. Sci. A: Polym. Chem., 51(6), 1417 (2013)

[29] Ghosh R, Das S, Chatterjee DP, Nandi AK, Langmuir, 32(33), 8413 (2016)

[30] Bernaerts KV, Du Prez FE, Prog. Polym. Sci, 31, 671 (2006)

[31] Wang Z, Wang Y, Xu D, Kong ESW, Zhang Y, Synth. Met., 160, 921 (2010)

[32] Wang CC, Tsai H, Shih HH, Jeon S, Xu Z, Williams D, Iyer S, Sanchez TC, Wang L, Cotlet M, ACS Appl. Mater. Interfaces, 2, 738 (2010)