Palladium-Catalyzed Synthesis of trans-4-(N,N-Bis(2-pyridyl)amino)stilbene. A New Intrinsic Fluoroionophore for Transition Metal Ions

• Published in: Organic letters Vol. 4; no. 5; pp. 777 - 780
• Main Authors: Yang, Jye-Shane, Lin, Yu-Hsi, Yang, Ching-Sheng
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.03.2002; Amer Chemical Soc
• Subjects: Biosensing Techniques - methods; Catalysis; Chemistry; Chemistry, Organic; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Fluorescent Dyes - metabolism; Ionophores - chemical synthesis; Ionophores - chemistry; Ionophores - metabolism; Ions - analysis; Ions - metabolism; Lead - analysis; Lead - metabolism; Metals, Heavy - analysis; Metals, Heavy - metabolism; Molecular Conformation; Nickel - analysis; Nickel - metabolism; Palladium - chemistry; Physical Sciences; Science & Technology; Spectrometry, Fluorescence; Stilbenes - chemical synthesis; Stilbenes - chemistry; Stilbenes - metabolism; Zinc - analysis; Zinc - metabolism; DESIGN; STATES; FLUORESCENCE; RECOGNITION; ONE-POT SYNTHESIS; TRIARYLAMINES; STILBENES; DIARYLAMINES; COMPLEXATION; NITROGEN BOND FORMATION
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol017260l

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.