BINOL-based foldamers--access to oligomers with diverse structural architectures.
In this article, we report on the synthesis and conformation of a new family of aromatic oligoamide foldamers based on binaphthol (BINOL) monomers. A series of oligomers with differing chirality of the individual BINOL building blocks and mixed sequences of alternate BINOL and pyridyl building blocks has been synthesized and structurally characterized. NMR and quantum chemical calculations on the basis of ab initio MO theory were performed to obtain insight into the conformational features of these oligomers. It is shown that the combination of these inherently chiral aromatic building blocks provides a novel access to a wide variety of conformationally ordered synthetic oligomers with diverse and dazzling structural architectures distinct from those classically observed.
Baruah
Pranjal K
PK
Division of Organic Synthesis, Central Material Characterization Division, and Central NMR Facility, National Chemical Laboratory, Doctor Homi Bhabha Road, Pune 411 008, India.
Gonnade
Rajesh
R
Rajamohanan
P R
PR
Hofmann
Hans-Jörg
HJ
Sanjayan
Gangadhar J
GJ
D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry
D009930:Organic Chemicals; D011725:Pyridines; C023666:pyridine