RSC Advances
Paper
1.0 mL minꢀ1 at 40 ꢁC. The sample concentration was 0.5 wt% was cooled down. An aliquot portion was then taken from the
and the injection volume was 50 mL. The calibration was per- crude product for the determination of the molar ratio of
1
formed using monodisperse polystyrene standards covering the different linkages and species by H NMR. Following this, the
molecular weight range from 580 to 460 000 Da. Infrared crude product was dissolved in dichloromethane (2 mL) and
spectra were measured by using a Brucker Vector 22 FT-IR precipitated from methanol (20 mL) three times. The yellow
ꢁ
spectrophotometer.
Matrix-assisted
laser
desorption precipitate was collected and dried under vacuum at 40 C for
ionization-time of ight (MALDI-TOF) mass spectra were overnight.
collected on a Bruker UltraFLEX MALDI-TOF mass spectrometer
in the linear mode. Potassium triuoroacetate was used as the
Conflicts of interest
cationization agent. Dithranol (DIT) was used as a matrix. Glass
transition temperature (Tg) of the polymer was determined by There are no conicts to declare.
differential scanning calorimetry (DSC) on a TA DSC-Q200
instrument. The sample was heated in two cycles from room
Acknowledgements
temperature to 120 ꢁC at a heating rate of 10 ꢁC minꢀ1 in
a nitrogen atmosphere. Tg was determined from the second run. We gratefully acknowledge the nancial support of the Distin-
Thermogravimetric analysis (TGA) was carried out on a Perkin- guished Young Investigator Fund of Zhejiang Province
Elmer Pyris 1 instrument under the N2 atmosphere at a heating (LR16B040001) and the National Science Foundation of the
rate of 10 ꢁC minꢀ1 from room temperature to 600 ꢁC. The People's Republic of China (no. 21474083).
refractive index (n) was measured by Spectroscopic
Ellipsometer.
Notes and references
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Synthesis of EGE and GGE
EGE was synthesized according to the previously reported
method.32 Eugenol (0.1 mol) and ECH (200 mL) were stirred in
a round-bottomed ask at 120 ꢁC. NaOH aqueous solution
(0.23 mol) was added dropwise over a period of 3.0 h. The
reaction was carried out for another 2.5 h. Following this, the
mixture was ltered to remove salt and concentrated with
a rotary evaporator to remove the excess of ECH and water. The
crude product went through the silica column eluted with DCM.
The white solid obtained was distilled over CaH2 under reduced
˜
3 M. J. Sanford, L. Pena Carrodeguas, N. J. Van Zee, A. W. Kleij
and G. W. Coates, Macromolecules, 2016, 49, 6394–6400.
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1
pressure. Yield: 84%. H NMR (400 MHz, CDCl3) d 6.86 (d, J ¼
8.0 Hz, 1H), 6.70 (d, J ¼ 9.7 Hz, 2H), 5.95 (dd, J ¼ 16.9, 10.1 Hz,
1H), 5.15–4.99 (m, 2H), 4.21 (dd, J ¼ 11.4, 3.5 Hz, 1H), 4.02 (dd, J
¼ 11.4, 5.5 Hz, 1H), 3.85 (s, 3H), 3.42–3.35 (m, 1H), 3.33 (d, J ¼
6.7 Hz, 2H), 2.91–2.84 (m, 1H), 2.72 (dd, J ¼ 4.9, 2.6 Hz, 1H). 13
C
NMR (101 MHz, CDCl3) d 149.53 (s), 146.29 (s), 137.53 (s), 133.83
(s), 120.47 (s), 115.70 (s), 114.35 (s), 112.38 (s), 70.43 (s), 55.84
(s), 50.24 (s), 44.93 (s), 39.80 (s).
GGE was synthesized from guaiacol via the similar method.
Yield: 82%. 1H NMR (400 MHz, CDCl3) d 7.01–6.85 (m, 4H), 4.24
(dd, J ¼ 11.4, 3.6 Hz, 1H), 4.05 (dd, J ¼ 11.4, 5.5 Hz, 1H), 3.87 (s,
3H), 3.44–3.35 (m, 1H), 2.93–2.86 (m, 1H), 2.74 (dd, J ¼ 4.9,
2.7 Hz, 2H). 13C NMR (101 MHz, CDCl3) d 149.65 (s), 148.00 (s),
121.96 (s), 120.96 (s), 114.24 (s), 111.95 (s), 70.23 (s), 55.88 (s),
50.24 (s), 44.98 (s).
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14 D. Kai, M. J. Tan, P. L. Chee, Y. K. Chua, Y. L. Yap and
X. J. Loh, Green Chem., 2016, 18, 1175–1200.
The copolymerization of COS and EGE (GGE)
All reactions were performed in the glovebox using a 10 mL or
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(salen)CrCl, cocatalyst, and EGE were added into the autoclave 17 J. Deng, B. Yang, C. Chen and J. Liang, ACS Sustainable
successively. The autoclave was pressurized to the appropriate
Chem. Eng., 2015, 3, 599–605.
pressure with COS and the reaction mixture was stirred at 0– 18 M. Luo, X.-H. Zhang, B.-Y. Du, Q. Wang and Z.-Q. Fan,
40 ꢁC for 0.1–2.0 h. Aer the copolymerization, the autoclave
49496 | RSC Adv., 2017, 7, 49490–49497
Macromolecules, 2013, 46, 5899–5904.
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