Organic Photocatalysts Based on Dithieno[3,2-b:2',3'-d]pyrrole for Photoinduced Metal-Free Atom Transfer Radical Polymerization

Nhung Thanh Thi Truong; Tam Huu Nguyen; Bao Kim Doan; Le-Thu T. Nguyen; Tam Hoang Luu; Chau Duc Tran; Thiet Quoc Nguyen; Ha Tran Nguyen

Macromolecular Research, Vol.29, No.11, 791-799, November, 2021

DOI10.1007/s13233-021-9085-5 Export Citation

Organic Photocatalysts Based on Dithieno[3,2-b:2',3'-d]pyrrole for Photoinduced Metal-Free Atom Transfer Radical Polymerization

Nhung Thanh Thi Truong¹, Tam Huu Nguyen¹, Bao Kim Doan¹, Le-Thu T. Nguyen^{2, †}, Tam Hoang Luu¹, Chau Duc Tran², Thiet Quoc Nguyen³, and Ha Tran Nguyen^{1, 2, †}

¹National Key Laboratory of Polymer and Composite Materials, Ho Chi Minh City 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 (HCMUT), Vietnam National University, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam
³Institute of Applied Materials Science, Vietnam Academy of Science and Technology, 01 TL29, District 12, Ho Chi Minh City, Vietnam

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In this research, three organic photocatalysts, 4-(4H-dithieno[3,2-b:2',3'- d]pyrrol-4-yl)-N,N-diphenylaniline, 4-(pyren-1-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole and 4-(6b,10-dihydroperylen-3-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole have been successfully synthesized through C-N coupling reactions. The chemical structures and the optical properties of the obtained organic photocatalysts have been characterized via 1H NMR,13C NMR, elemental analysis, and UV-Vis spectroscopy. Next, these dithieno[3,2-b:2′,3′-d]pyrrole-based photocatalysts have been used for the polymerization of methyl methacrylate, 2-(dimethylamino)ethyl methacrylate and tert-butyl methacrylate monomers under 365 nm UV irradiation, resulting in (meth)acrylate polymers with controlled molecular weights and low polydispersity indexes.

Keywords:4H-dithieno[3,2-b:2',3'-d]pyrrole;metal-free atom transfer radical polymerization;organic photocatalyst;controlled polymerization;UV irradiation

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

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[4] Matyjaszewski K, Spanswick J, Mater. Today, 8, 26 (2005)

[5] Braunecker WA, Matyjaszewski K, Prog. Polym. Sci, 32, 93 (2007)

[6] Kato M, Kamigaito M, Sawamoto M, Higashimura T, Macromolecules, 28(5), 1721 (1995)

[7] Patten TE, Xia JH, Abernathy T, Matyjaszewski K, Science, 272(5263), 866 (1996)

[8] Pintauer T, Matyjaszewski K, Chem. Soc. Rev., 37, 1087 (2008)

[9] Prier CK, Rankic DA, MacMillan DWC, Chem. Rev., 113(7), 5322 (2013)

[10] Schultz DM, Yoon TP, Science, 343, 123917 (2014)

[11] Aguirre-Soto A, Lim CH, Hwang AT, Musgrave CB, Stansbury JW, J. Am. Chem. Soc., 136(20), 7418 (2014)

[12] Theriot JC, Lim CH, Yang H, Ryan MD, Musgrave CB, Miyake GM, Science, 352(6289), 1082 (2016)

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

[15] Pan X, Lamson M, Yan J, Matyjaszewski K, ACS Macro Lett., 4, 192 (2015)

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[17] Shang TY, Lu LH, Cao Z, Liu Y, He WM, Yu B, Chem. Commun., 55, 5408 (2019)

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[20] Pan H, Wu Y, Li Y, Liu P, Ong BS, Zhu S, Xu G, Adv. Funct. Mater., 17(17), 3574 (2007)

[21] Li YN, Wu YL, Liu P, Birau M, Pan HL, Ong BS, Adv. Mater., 18(22), 3029 (2006)

[22] Lim ZB, Xue BF, Bomma S, Li HR, Sun SY, Lam YM, Belcher WJ, Dastoor PC, Grimsdale AC, J. Polym. Sci. A: Polym. Chem., 49(20), 4387 (2011)

[23] Zhang X, Steckler TT, Dasari RR, et al., J. Mater. Chem., 20, 123 (2010)

[24] Hu L, Qiao W, Zhou X, Han J, Zhang X, Ma D, Li Y, Wang ZY, Polym. Chem., 8, 2055 (2017)

[25] Fortsch S, Vogt A, Bauerle P, J. Phys. Org. Chem., 30, e3743 (2017)

[26] Matyjaszewski K, Jakubowski W, Min K, Tang W, Huang J, Braunecker WA, Tsarevsky NV, Proc. Natl. Acad. Sci., 103, 15309 (2006)

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