Summary
The backbone of polyethers are often flexible because of inherent characteristics of ether linkage, but polyethers from chiral epoxides could form stable one-handed helical structure in solution state, if the pendants on the chain of polyethers are enough bulky and the distance between pendants and main chain is appropriate.
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Optically active 4,4,4-triphenyl-1,2-butanediol, 1HNMR (CDCl3): δ=7.18-7.37 (m, 15H, PhH), 3.75-3.80(m, 1H, - CH-), 3.14 (dd, J1-4.1Hz, J2=14.8Hz 1H,- CH2-), 3.01-3.05 (m, 1H, -CH2-), 2.82-2.86 (m, 1H, -CH2-), 2.67 (dd, J1-5.2 Hz, J2=14.8Hz, 1H, -CH2-CPh3), 1.86 (m, 12H, -OH), 1.25 (m, 1H, -OH); 13CNMR(CDCl3): δ= 146.63, 129.02, 128.21, 126.36, 69.46, 56.05, 50.88, 45.13. [α]58920= -38o (c 0.2, THF)
Optically active 4,4,4-triphenyl-1-tert-butoxyl-2-butanol, 1HNMR (CDCl3): δ=7.12-7.35 (m, 15H, PhH), 3.61-3.64 (m, 1H, - CH-), 2.99 (dd, 1H, J1=2.8Hz, J2=14.7Hz, -CH2-CPh3), 2.76-2.81 (m, 1H, -CH2-), 2.54 (dd, 1H, J=5.3Hz, J=14.6Hz, -CH2-CPh3), 2.36 (dd, 1H, m, 1H, -CH2-), 2.16 (m, 1H, -OH), 0.98 (s, 9H, -C(CH3)3); 13CNMR(CDCl3): δ= 146.26, 128.92, 128.33, 126.15, 69.22, 68.13, 55.92, 50.35.88, 45.13, 29.56.[α]58920 = -37o (c 0.2, THF)
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Cao, J., Yang, NF., Li, JC. et al. Helical Polymers from Optically Active Epoxides with Bulky Pendants. Polym. Bull. 59, 481–490 (2007). https://doi.org/10.1007/s00289-007-0788-3
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DOI: https://doi.org/10.1007/s00289-007-0788-3