2,7-Bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine: an ultrasensitive fluorescent probe for glucopyranoside.
[structure: see text] A push-pull conjugated molecule, 2,7-bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine (BPN), has been designed to bind selectively with octyl glucopyranoside (OGU). The BPN/OGU quadruple hydrogen-bonding complex adopts a rigid BPN conformation in which the proton donor (d) and acceptor (a) relays (daad) are resonantly conjugated through the ethynyl bridge, inducing pi-electron delocalization, i.e., a charge transfer effect. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of approximately 100 pM.
Liao
Jen-Hai
JH
Department of Chemistry, National Taiwan University, Taipei, 106, Republic of China.
Chen
Chao-Tsen
CT
Chou
He-Chun
HC
Cheng
Chung-Chih
CC
Chou
Pi-Tai
PT
Fang
Jim-Min
JM
Slanina
Zdenek
Z
Chow
Tashin J
TJ
D001665:Binding Sites; D005456:Fluorescent Dyes / Q000138:chemical synthesis; D005960:Glucosides / Q000032:analysis*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D012680:Sensitivity and Specificity; D013057:Spectrum Analysis
C471502:2,7-bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine; D005456:Fluorescent Dyes; D005960:Glucosides; D009287:Naphthyridines; D011758:Pyrroles; C018619:octyl-beta-D-glucoside