1NM2: bp 25 ꢁC/0.5 Torr; 1H NMR (300 MHz, CDCl3): d 0.12
(s, 9H, Si(CH3)3), 3.38 (s, 3H, CH3-O), 3.54–3.59 (m, 4H,
OCH2CH2OCH3), 3.63–3.66(m, 2H, SiOCCH2), 3.73–3.80 (t,
2H, SiOCH2); 13C NMR (300 MHz, CDCl3): 73.04, 72.42, 62.38,
59.48, 0.0; 29Si NMR (500 MHz, CDCl3): 16.0; Anal. Calcd for
C8H20O3Si: C, 49.96; H, 10.48. Found: C, 49.73; H, 10.68%.
1NM3: bp 52 ꢁC/0.5 Torr; 1H NMR (300 MHz, CDCl3): d 0.09
(s, 9H, Si(CH3)3), 3.36 (s, 3H, CH3–O), 3.52–3.57 (m, 4H,
OCH2CH2OCH3), 3.63–3.65 (m, 6H, SiOCCH2OCH2CH2O),
3.71–3.74 (t, 2H, SiOCH2); 13C NMR (300 MHz, CDCl3): 73.04,
72.43, 71.10, 71.08, 70.95, 62.49, 59.1, 0.0; 29Si NMR (500 MHz,
CDCl3): 16.1; Anal. Calcd for C10H24O4Si: C, 50.81; H, 10.23.
Found: C, 50.72; H, 10.29%.
Acknowledgements
We thank 3M Co. for the gift of LiN(CF3SO2)2. Instrumentation
at Grinnell was funded by the NSF-MRI program (Grant No.
0116159). The NMR instruments in this research were funded by
NIH (Grants NIH 1 S10 RRO 8389-01, 1 S10 RRO8389-01, 1
S10 RRO4981-01, and CHE-9629688).
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1NM4: bp 87 ꢁC/0.5 Torr; 1H NMR (300 MHz, CDCl3):
d 3.69–3.73(t, 2H, SiOCH2), 3.51–3.64 (m, 14H, OCH2CH2O),
3.36 (s, 3H, CH3-O), 0.094 (s, 9H, SiCH3); 13C NMR (300 MHz,
CDCl3): 73.0, 72.38, 71.07, 71.05, 71.02, 70.96, 62.40, 59.44, 0.0;
29Si NMR (500 MHz, CDCl3): 16.8; Anal. Calcd for C12H28O5Si:
C, 51.39; H, 10.06. Found: C, 51.59; H, 10.37%.
1
1NM5: bp 122 ꢁC/0.5 Torr; H NMR (300 MHz, CDCl3):
d 3.67–3.71 (t, 2H, SiOCH2), 3.59–3.62 (m, 12H, OCH2CH2O),
3.33 (s, 3H, CH3-O), 0.07 (s, 9H, SiCH3); 13C NMR (300 MHz,
CDCl3): 73.0, 72.38, 71.07, 71.05, 71.02, 70.96, 62.40, 59.44,
0.002; 29Si NMR (500 MHz, CDCl3): 17.1. Anal. Calcd for
C14H30O6Si: C, 51.82; H, 9.94. Found: C, 52.27; H, 10.25%.
1NM7.2: bp 125–128 ꢁC/0.5 Torr; 1H NMR (300 MHz,
CDCl3): d 3.69 (t, 2H, SiOCH2), 3.49–3.62 (m, 25H, OCH2-
CH2O), 3.34 (s, 3H, CH3-O), 0.07 (s, 9H, SiCH3); 13C NMR (300
MHz, CDCl3): 73.0, 72.36, 71.00, 71.01, 71.02, 70.96, 62.38,
59.41, 0.00; 29Si NMR (500 MHz, CDCl3): 17.2; Anal. Calcd for
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C
18.4H40.8O8.2Si: C, 52.44; H, 9.76. Found: C, 51.90; H, 10.07%.
ꢁ
1
2NM3N1: bp 62 C/0.5 Torr; H NMR (300 MHz, CDCl3):
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d 3.70–3.73 (t, 4H, SiOCH2), 3.62 (s, 4H, SiOCCH2), 3.53–3.56 (t,
4H, SiOCCCH2), 0.10 (s, 18H, SiCH3); 13C NMR (300 MHz,
CDCl3): 73.02, 71.09, 62.41, 59.44, 0.001; 29Si NMR (500 MHz,
CDCl3): 17.9; Anal. Calcd for C12H30O4Si2: C, 48.93; H, 10.27.
Found: C, 48.74; H,ꢁ10.28%.
1
2NM4N1: bp 88 C/0.5 Torr; H NMR (300 MHz, CDCl3):
d 3.63–3.73 (t, 4H, SiOCH2), 3.63 (s, 8H, SiOCCCH2CH2O),
3.52–3.56 (t, 4H, SiOCCCH2), 0.10 (s, 18H, SiCH3); 13C NMR
(300 MHz, CDCl3): 73.02, 71.04, 62.48, 0.001; 29Si NMR (500
MHz, CDCl3): 17.5; Anal. Calcd for C14H34O5Si2: C, 49.96; H,
10.12. Found: C, 49.87; H, 10.35%.
1NGeM2
(methoxyethoxyethoxy-trimethylgermane):
28 Y. Choquette, G. Brisard, M. Parent, D. Brouillette, G. Perron,
J. E. Desnoyers, M. Armand, D. Gravel and N. Slougui,
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1NGeM2 was synthesized by refluxing trimethylchlorogermane
(12g, 78.4mmol) and diethylene glycol monomethyl ether (11.3 g,
94 mmol) in 50 mL dry THF in the presence of triethylamine (10
g, 0.1 mol). The pure product was obtained as a colorless oil (13
g, 70%) by distillation twice under reduced pressure; bp 26 ꢁC/0.5
mmHg; 1H NMR (300 MHz, CDCl3): d 0.40 (s, 9H, Ge(CH3)3),
3.37 (s, 3H, CH3-O), 3.52–3.58 (m, 4H, OCH2CH2OCH3), 3.62–
3.66 (m, 2H, GeOCCH2), 3.74 (t, 2H, GeOCH2); 13C NMR (300
MHz, CDCl3): 73.25, 71.12, 70.26, 63.29, 58.65, 0.001.
33 M. C. Smart, J. F. Whitacre, B. V. Ratnakumar and K. Amine,
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This journal is ª The Royal Society of Chemistry 2008
J. Mater. Chem., 2008, 18, 3713–3717 | 3717