"Inverse vulcanisation" polymerisation of elemental sulphur with 1,3-diisopropenylbenzene; poly(sulphur-m-diisopropenylbenzene)
Submitted Oct 29, 2015, published Oct 29, 2015
Sulphur, S8 (≥ 99.5 %, Sigma Aldrich Ltd.).
1,3-diisopropenylbenzene (> 97 %, TCI).
The following protocol is for 50 wt.% 1,3-diisopropenylbenzene poly(sulphur-m-diisopropenylbenzene): Elemental sulphur (2 g, 7.81 mmol in terms of S8 units) was added to a 20 ml glass vial with a stirrer bar. Separately, an oil bath was heated to 185 °C and the vial containing the sulphur lowered into the bath carefully. Once melted and under vigorous stirring, 1,3-diispropenylbenzene (2.16 ml, 12.6 mmol) was rapidly injected and the two-phase mixture further agitated with a glass rod to ensure complete mixing. After 5 minutes, the mixture was poured into a silicone mould and placed in an oven at 200 °C for 30 minutes. After 30 minutes, the mould containing the polymer was removed from the oven and cooled to room temperature naturally giving the target compound, poly(sulphur-m-diisopropenylbenzene).
Calc. for S16C20H24 (MW 777.44): C,30.90; H, 3.11; S, 65.99. Anal. Found: C, 35.85; H, 3.55; S, 56.17.
J. C. Bear, W. J. Peveler, P. D. McNaughter, I. P. Parkin, P. O’Brien and C. W. Dunnill, Chem. Commun., 2015, 51, 10467–10470.
W. J. Chung, J. J. Griebel, E. T. Kim, H. Yoon, A. G. Simmonds, H. J. Ji, P. T. Dirlam, R. S. Glass, J. J. Wie, N. A. Nguyen, B. W. Guralnick, J. Park, Á. Somogyi, P. Theato, M. E. Mackay, Y.-E. Sung, K. Char and J. Pyun, Nat. Chem., 2013, 5, 518–524.
5 percent and 40 percent DIB S polymers in molds.jpeg
Melted and cast elemental sulphur with no 1,3-diisopropenylbenzene in "dog-bone" mould (yellow, top) and 50 wt.% 1,3-diisopropenylbenzene poly(sulphur-m-diisopropenylbenzene) (red, bottom).
Keywords: aromatics/arenes, inverse vulcanisation, polymerization, sulphides