Phenothiazine Derivative as Organic Photocatalyst for Metal Free Atom Transfer Radical Polymerization

Hoan Minh Tran; Lan Ngoc Tan Phan; Thang Van Le; Thuy Thuy Truong; Tam Huu Nguyen; Khuong Tung Truong; Le-Thu T. Nguyen; Mai Thanh Phong; Ha Tran Nguyen

Polymer(Korea), Vol.43, No.4, 496-502, July, 2019

DOI10.7317/pk.2019.43.4.496 Export Citation

Phenothiazine Derivative as Organic Photocatalyst for Metal Free Atom Transfer Radical Polymerization

Hoan Minh Tran¹, Lan Ngoc Tan Phan¹, Thang Van Le^{2, 3}, Thuy Thuy Truong¹, Tam Huu Nguyen¹, Khuong Tung Truong¹, Le-Thu T. Nguyen^{1, 2}, Mai Thanh Phong⁴, and Ha Tran Nguyen^{1, 2, †}

¹National Key Laboratory of Polymer and Composite Materials, University of Technology, Vietnam National University –Ho Chi Minh City (VNU–HCM), 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam
²Faculty of Materials Technology, Ho Chi Minh City University of Technology, Vietnam National University, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam
³Materials Technology Key Laboratory (Mtlab), Ho Chi Minh City University of Technology, Vietnam National University, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam
⁴Faculty of Chemical Engineering, Ho Chi Minh City University of Technology (HCMUT), Vietnam National University, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam

E-mail:

A novel organic photocatalyst, 4-(10H-phenothiazin-10-yl)-N,N-diphenylaniline (PDPA) has been successfully synthesized from triphenylamine and phenothiazine moiety via Buchwald-Hartwig C-N coupling. The chemical structure of catalyst was characterized via proton nuclear magnetic resonance (1H NMR) and the optical properties were investigated via UV-vis spectroscopy. The PDPA has been applied as an organic photocatalyst for metal free atom transfer radical polymerization (O-ATRP). The well-controlled molecular weights of polymethacrylates have been obtained with high yield of 95% and narrow polydispersity index (đ).

Keywords:phenothiazine;organic photocatalyst;metal-free atom transfer radical polymerization;Buchwald-Hartwig C-N coupling;methacrylate monomers

[References]

Fukuda T, Terauchi T, Goto A, Ohno K, Tsujii Y, Miyamoto T, Kobatake S, Yamada B, Macromolecules, 29(20), 6393 (1996)
Matyjaszewsk K, Davis TP, Editors, Handbook of radical polymerization, John Wiley & Sons, Hobo Ken, 2002.
Nicolas J, Dire C, Mueller L, Belleney J, Charleux B, Marque SRA, Bertin D, Magnet S, Couvreur L, Macromolecules, 39(24), 8274 (2006)
Matyjaszewski K, Chem. Eur. J., 5, 3095 (1999)
Matyjaszewski K, Macromolecules, 45(10), 4015 (2012)
Matyjaszewski K, Xia JH, Chem. Rev., 101(9), 2921 (2001)
Wang JS, Matyjaszewski K, J. Am. Chem. Soc., 117(20), 5614 (1995)
Cheng C, Khoshdel E, Wooley KL, NanoLett., 6, 1741 (2006)
Vogt AP, Sumerlin BS, Soft Matter, 5, 2347 (2009)
Matyjaszewski K, Tsarevsky NV, J. Am. Chem. Soc., 136(18), 6513 (2014)
Matyjaszewski K, Pintauer T, Gaynor S, Macromolecules, 33(4), 1476 (2000)
Munirasu S, Aggarwal R, Baskaran D, Chem. Commun., 4518 (2009).
Shen YQ, Zhu SP, Macromolecules, 34(25), 8603 (2001)
Fors BP, Hawker CJ, Angew. Chem.-Int. Edit., 51, 8850 (2012)
Francesco DB, Fantin FM, Abdirisak AI, Armando G, Polym. Chem., 9, 646 (2018)
Fantin M, Park S, Wang Y, Matyjaszewski K, Macromolecules, 49(23), 8838 (2016)
Theriot JC, McCarthy BG, Lim CH, Miyake GM, Macromol. Rapid Commun., 38, 170004 (2017)
Yilmaz G, Yagci Y, Polym. Chem., 9, 1757 (2018)
Miyake GM, Theriot JC, Macromolecules, 47(23), 8255 (2014)
Pearson RM, Lim CH, McCarthy BG, Musgrave CB, Miyake GM, J. Am. Chem. Soc., 138(35), 11399 (2016)
Kutahya C, Allushi A, Isci R, Kreutzer J, Ozturk T, Yilmaz G, Yagci Y, Macromolecules, 50(17), 6903 (2017)

[1] Fukuda T, Terauchi T, Goto A, Ohno K, Tsujii Y, Miyamoto T, Kobatake S, Yamada B, Macromolecules, 29(20), 6393 (1996)

[2] Matyjaszewsk K, Davis TP, Editors, Handbook of radical polymerization, John Wiley & Sons, Hobo Ken, 2002.

[3] Nicolas J, Dire C, Mueller L, Belleney J, Charleux B, Marque SRA, Bertin D, Magnet S, Couvreur L, Macromolecules, 39(24), 8274 (2006)

[4] Matyjaszewski K, Chem. Eur. J., 5, 3095 (1999)

[5] Matyjaszewski K, Macromolecules, 45(10), 4015 (2012)

[6] Matyjaszewski K, Xia JH, Chem. Rev., 101(9), 2921 (2001)

[7] Wang JS, Matyjaszewski K, J. Am. Chem. Soc., 117(20), 5614 (1995)

[8] Cheng C, Khoshdel E, Wooley KL, NanoLett., 6, 1741 (2006)

[9] Vogt AP, Sumerlin BS, Soft Matter, 5, 2347 (2009)

[10] Matyjaszewski K, Tsarevsky NV, J. Am. Chem. Soc., 136(18), 6513 (2014)

[11] Matyjaszewski K, Pintauer T, Gaynor S, Macromolecules, 33(4), 1476 (2000)

[12] Munirasu S, Aggarwal R, Baskaran D, Chem. Commun., 4518 (2009).

[13] Shen YQ, Zhu SP, Macromolecules, 34(25), 8603 (2001)

[14] Fors BP, Hawker CJ, Angew. Chem.-Int. Edit., 51, 8850 (2012)

[15] Francesco DB, Fantin FM, Abdirisak AI, Armando G, Polym. Chem., 9, 646 (2018)

[16] Fantin M, Park S, Wang Y, Matyjaszewski K, Macromolecules, 49(23), 8838 (2016)

[17] Theriot JC, McCarthy BG, Lim CH, Miyake GM, Macromol. Rapid Commun., 38, 170004 (2017)

[18] Yilmaz G, Yagci Y, Polym. Chem., 9, 1757 (2018)

[19] Miyake GM, Theriot JC, Macromolecules, 47(23), 8255 (2014)

[20] Pearson RM, Lim CH, McCarthy BG, Musgrave CB, Miyake GM, J. Am. Chem. Soc., 138(35), 11399 (2016)

[21] Kutahya C, Allushi A, Isci R, Kreutzer J, Ozturk T, Yilmaz G, Yagci Y, Macromolecules, 50(17), 6903 (2017)