Palladium-catalyzed synthesis of trans-4-(N,N-bis(2-pyridyl)amino)stilbene. A new intrinsic fluoroionophore for transition metal ions.
[reaction: see text] The title compound (1) has been synthesized via sequential Pd-catalyzed amination reactions and investigated as an intrinsic fluoroionophore. The efficiency in the synthesis of 1 strongly depends on the order of couplings among the substrates. Compound 1 displays fluorescence quenching upon the binding of transition metal ions, where the binding-triggered conformational twisting and in turn the inhibition of internal charge transfer (ICT) play an important role.
Yang
Jye-Shane
JS
Department of Chemistry, National Central University, Chung-Li, Taiwan 32054. jsyang@cc.ncu.edu.tw
Lin
Yu-Hsi
YH
Yang
Ching-Sheng
CS
D015374:Biosensing Techniques / Q000379:methods; D002384:Catalysis; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007476:Ionophores / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007477:Ions / Q000032:analysis / Q000378:metabolism; D007854:Lead / Q000032:analysis / Q000378:metabolism; D019216:Metals, Heavy / Q000032:analysis* / Q000378:metabolism; D008968:Molecular Conformation; D009532:Nickel / Q000032:analysis / Q000378:metabolism; D010165:Palladium / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D015032:Zinc / Q000032:analysis / Q000378:metabolism
C467074:4-(N,N-bis(2-pyridyl)amino)stilbene; D005456:Fluorescent Dyes; D007476:Ionophores; D007477:Ions; D019216:Metals, Heavy; D013267:Stilbenes; D007854:Lead; D010165:Palladium; D009532:Nickel; D015032:Zinc