Self-assembling structures of long-chain phenyl glucoside influenced by the introduction of double bonds.
Four long-chain phenyl glucoside amphiphiles possessing a saturated or unsaturated long alkyl chain group as the self-assembling unit of a highly organized molecular architecture were synthesized. Their self-assembling properties were investigated by EF-TEM, SEM, CD, FT-IR, and XRD. Compound 2 possessing one double bond in the lipophilic portion showed twisted helical fibers, which formed a bilayered structure with a 3.59 nm period, while compound 3 showed the helical ribbons and left-handed nanotubular structures with 150-200 nm inner diameters and ca. 20 nm of wall. Very interestingly, compound 4 possessing three double bonds showed a nanotubular structure with ca. 70 nm of inner diameter through a helical ribbon, which formed a loose bilayered structure with 4.62 nm. These results indicate that self-assembling properties strongly depend on the number of cis double bonds.
CREST, Japan Science and Technology Corporation (JST), Nanoarchitectonics Research Center (NARC), National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 4, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8562, Japan.
Jong Hwa
JH
Jung
George
G
John
Kaname
K
Yoshida
Toshimi
T
Shimizu
D002942:Circular Dichroism; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry*; D008854:Microscopy, Electron; D010647:Phenyl Ethers / Q000138:chemical synthesis / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D014961:X-Ray Diffraction
D005960:Glucosides; D010647:Phenyl Ethers