Dynamic Covalent Polymerization of Chalcogenide Hybrid Inorganic/Organic Polymer Resins with Norbornenyl Comonomers

Minho Kwon; Hongchan Lee; Seo-Hui Lee; Heung Bae Jeon; Min-Cheol Oh; Jeffrey Pyun; Hyun-jong Paik

Macromolecular Research, Vol.28, No.11, 1003-1009, October, 2020

DOI10.1007/s13233-020-8136-7 Export Citation

Dynamic Covalent Polymerization of Chalcogenide Hybrid Inorganic/Organic Polymer Resins with Norbornenyl Comonomers

Minho Kwon, Hongchan Lee, Seo-Hui Lee¹, Heung Bae Jeon¹, Min-Cheol Oh², Jeffrey Pyun^{3, †}, and Hyun-jong Paik^†

Department of Polymer Science, Pusan National University, Pusan 46241, Korea
¹Department of Chemistry, Kwangwoon University, Seoul 01897, Korea
²Department of Electronics Engineering, Pusan National University, Pusan 46241, Korea
³Department of Chemistry & Biochemistry, University of Arizona, Tucson, Arizona, USA

E-mail:,

Elemental sulfur (S8) is an inexpensive chemical feedstock for polymeric materials but has the disadvantages of poor solubility in organic media and inferior physical properties in the elemental form. We report on the preparation of organosulfur chalcogenide hybrid inorganic/organic polymer (CHIPs) based on bifunctional norbornene comonomers using dynamic covalent polymerization (DCP). A poly(sulfur-random-styrene) (p(S-r-Sty)) resin was utilized to address the limited solubility/ miscibility of norbornene-containing comonomers in liquid sulfur. This report demonstrated the ability to expand the scope of organic comonomers to prepare organosulfur CHIPs from elemenatal sulfur using a combination of inverse vulcanization and dynamic covalent polymerization.

Keywords:sulfur polymerization;dynamic covalent polymerization;inverse vulcanization;norbornenes;norbornyl comonomers

[References]

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[Referenced By]

[1] Chung WJ, Simmonds AG, Griebel JJ, Kim ET, Suh HS, Shim IB, Glass RS, Loy DA, Theato P, Sung YE, Angew. Chem.-Int. Edit., 50, 11409 (2011)

[2] Parker D, Jones H, Petcher S, Cervini L, Griffin J, Akhtar R, Hasell T, J. Mater. Chem., A, 5, 11682 (2017)

[3] Griebel JJ, Namnabat S, Kim ET, Himmelhuber R, Moronta DH, Chung WJ, Simmonds AG, Kim KJ, van der Laan J, Nguyen NA, Dereniak EL, Mackay ME, Char K, Glass RS, Norwood RA, Pyun J, Adv. Mater., 26(19), 3014 (2014)

[4] Griebel JJ, Nguyen NA, Namnabat S, Anderson LE, Glass RS, Norwood RA, Mackay ME, Char K, Pyun J, ACS Macro Lett., 4, 862 (2015)

[5] Kleine TS, Nguyen NA, Anderson LE, Namnabat S, LaVilla EA, Showghi SA, et al., ACS Macro Lett., 5, 1152 (2016)

[6] Anderson LE, Kleine TS, Zhang Y, Phan DD, Namnabat S, et al., ACS Macro Lett., 6, 500 (2017)

[7] Zhang Y, Konopka KM, Glass RS, Char K, Pyun J, Polym. Chem., 8, 5167 (2017)

[8] Zhang Y, Kleine TS, Carothers KJ, Phan DD, Glass RS, Mackay ME, Char K, Pyun J, Polym. Chem., 9, 2290 (2018)

[9] Kleine TS, Diaz LR, Konopka KM, Anderson LE, Pavlopolous NG, et al., ACS Macro Lett., 7, 875 (2018)

[10] Zhang Y, Glass RS, Char K, Pyun J, Polym. Chem., 10, 4078 (2019)

[11] Kim ET, Chung WJ, Lim J, Johe P, Galss RS, Pyun J, Char K, Polym. Chem., 10, 3617 (2014)

[12] Oschmann B, Park J, Kim C, Char K, Sung YE, Zentel R, Chem. Mater., 27, 7011 (2015)

[13] Talapaneni SN, Hwang TH, Je SH, Buyukcakir O, Choi JW, Coskun A, Angew. Chem.-Int. Edit., 55, 3106 (2016)

[14] Arslan M, Kiskan B, Cengiz EC, Demir-Cakan R, Yagci Y, Eur. Polym. J., 80, 70 (2016)

[15] Kleine TS, Lee T, Carothers KJ, Hamilton MO, Anderson LE, et al., Angew. Chem.-Int. Edit., 58, 17656 (2019)

[16] Wu X, Smith JA, Petcher S, Zhang B, Parker DJ, Griffin JM, Hasell T, Nat. Commun., 10, 1 (2019)

[17] Shukla S, Ghosh A, Roy PK, Mitra S, Lochab B, Polymer, 99, 349 (2016)

[18] Akkus B, Kiskan B, Yagci Y, Polymer Chemistry, 10, 5743 (2019)

[19] Lin HK, Liu YL, Macromol. Rapid Commun., 39, 170083 (2018)

[20] Park S, Lee D, Cho H, Lim J, Char K, ACS Macro Lett., 8, 1670 (2019)

[21] Lee JH, Kim KH, Choi M, Jeon J, Yoon HJ, Choi J, Lee YS, Lee M, Wie JJ, Nano Energy, 66, 104158 (2019)

[22] Crockett MP, Evans AM, Worthington MJ, Albuquerque IS, et al., Angew. Chem.-Int. Edit., 55, 1714 (2016)

[23] Simmonds AG, Griebel JJ, Park J, Kim KR, Chung WJ, Oleshko VP, et al., ACS Macro Lett., 3, 229 (2014)

[24] Dirlam PT, Glass RS, Char K, Pyun J, J. Polym. Sci. A: Polym. Chem., 55(10), 1635 (2017)

[25] Zhang YY, Pavlopoulos NG, Kleine TS, Karayilan M, Glass RS, Char K, Pyun J, J. Polym. Sci. A: Polym. Chem., 57(1), 7 (2019)

[26] Westerman CR, Jenkins CL, Macromolecules, 51(18), 7233 (2018)

[27] Griebel JJ, Glass RS, Char K, Pyun J, Prog. Polym. Sci, 58, 90 (2016)

[28] Zhang YY, Griebel JJ, Dirlam PT, Nguyen NA, Glass RS, Mackay ME, Char K, Pyun J, J. Polym. Sci. A: Polym. Chem., 55(1), 107 (2017)

[29] Yokoyama Y, JP Patent JP2010047547 (2010).

[30] Yarabe HH, Rugutt JK, McCarroll ME, Warner IM, Electrophoresis, 21(10), 2025 (2000)