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Citation: WU Si-Lin, DENG Rui-Hong, CAO Qian-Yong, LIU Jing-Hua. Synthesis and Spectroscopic Characterization of a Novel Polypyridine Compound with Phosphonic Acid Group[J]. Chinese Journal of Applied Chemistry, ;2008, 25(4): 445-448. shu

Synthesis and Spectroscopic Characterization of a Novel Polypyridine Compound with Phosphonic Acid Group

1.
Department of Chemistry, Nanchang University, Nanchang 330031

Corresponding author: CAO Qian-Yong,
Received Date: 11 April 2007
Available Online: 10 September 2007
Fund Project: 江西省教育厅(赣教技字[2006]29号)资助项目 (赣教技字[2006]29号)

A novel polypyridine compound,6-(4-phenylphosphonic acid)-2,2'-bipyridine,was synthesized from 1-(4-bromophenyl) ethanone as raw material followed by four-step reactions:Mannich salt-producing reaction,Krohnke ring-coupling reaction,HIRAO aryl C-P coupling reaction of phosphonate and McKenna hydrolyzation of phosphonate.The intermediates and the target product were characterized by IR,MS and ¹H NMR.The dissociation constants with pK_a1 and pK_a2 values of 6.2 and 2.0 measured by the potentiometric titration method are comparable to those by the absorption and emission spectra titration methods.Absorption and emission spectra of the compound show sensitivity to pH value.Electronic absorption titration studies show that the absorption bands at 322 nm,270 nm and 241 nm were blue shifted to 292 nm,262 nm and 234 nm respectively with increasing the pH value,and three isosbestic points were observed at 310 nm,280 nm and 262 nm.The corresponding emission titration studies demonstrate that the emission band at 428 nm was blue shifted to 353 nm with increasing the pH value,with an isoemissive point at 380 nm.The mechanism of sensi-tivity to pH value was also discussed.
- (phenylphosphonic acid) bipyridine,
- synthesis,
- potentiometric titration,
- absorption spectrum,
- emission spectrum
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