Chiral poly(ureidophthalimide) foldamers in water.
Poly(ureidophthalimide)s decorated with hydrophilic side chains, that ensure solubility in aqueous media, have been synthesized and characterized by UV/Vis and circular dichroism (CD) spectroscopy. Temperature and concentration dependent CD measurements in water have revealed an almost temperature and concentration independent Cotton effect, indicative for a strong intramolecular organization. Similar studies in THF demonstrate the dynamic nature of the secondary architecture, a characteristic of foldamers. In addition, the bisignated Cotton effect in water is opposite in sign to that in THF, suggestive for a solvent-dependent preference for one helical handedness. Mixing experiments prove the dominance of water in determining the handedness of the helical architecture. The solvent allows for control over the helical architecture and thus governs the supramolecular synthesis.
Sinkeldam
Renatus W
RW
Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven, The Netherlands.
van Houtem
Michel H C J
MH
Pieterse
Koen
K
Vekemans
Jef A J M
JA
Meijer
E W
EW
D002942:Circular Dichroism / Q000379:methods; D005027:Ethylene Oxide / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D010797:Phthalimides / Q000138:chemical synthesis / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry; D012995:Solubility; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013696:Temperature; D014867:Water / Q000737:chemistry
D010797:Phthalimides; D011108:Polymers; C516576:poly(ureidophthalimide); D014867:Water; D005027:Ethylene Oxide