Chirality-sensing binaphthocrown ether-polythiophene conjugate.
An enantiomeric binaphthyl unit was tethered to adjacent thiophenes with oxyethylene linkers to give a chiral polythiophene with binaphthocrown ether cavities. Upon inclusion of a chiral cationic guest in the cavity of the chiral crown ether-polythiophene conjugate, the bithiophene unit was twisted to shorten the effective conjugation length of polythiophene backbone, enabling us to sense the guest binding by reading out the amplified optical signal gains arising from the backbone structure change. This strategy allowed us to discriminate the guest chirality without using chiroptical signals or a circular dichroism spectrometer to achieve the highest enantioselectivity of 7.3 for valine methyl ester with a 40-fold enhanced sensitivity compared with the corresponding monomeric sensor.
Fukuhara
Gaku
G
Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan. gaku@chem.eng.osaka-u.ac.jp
Inoue
Yoshihisa
Y
D000596:Amino Acids / Q000737:chemistry*; D002942:Circular Dichroism; D043844:Crown Ethers / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism; D013876:Thiophenes / Q000737:chemistry*
D000596:Amino Acids; D043844:Crown Ethers; D004987:Ethers; D011108:Polymers; D013876:Thiophenes; C066730:polythiophene