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Citation: XU Haiyun, LIU Qifeng, SONG Shengmei. Synthesis and Properties of Fluorescent Probe for Monosaccharides Based on Exocyclic Ring-Fused Boron Dipyrromethene Dye Substituted with Phenylboronic Ester[J]. Chinese Journal of Applied Chemistry, ;2014, 31(12): 1405-1412. doi: 10.3724/SP.J.1095.2014.30591 shu

Synthesis and Properties of Fluorescent Probe for Monosaccharides Based on Exocyclic Ring-Fused Boron Dipyrromethene Dye Substituted with Phenylboronic Ester

1.
College of Chemistry and Chemical Engineering, Shangqiu Normal College, Shangqiu 476000, China

Corresponding author: XU Haiyun,
Received Date: 25 November 2013
Available Online: 28 May 2014
Fund Project: 国家自然科学基金(21205076) (21205076)河南省科技厅基础与前沿技术研究(112300410309) (112300410309)河南省教育厅自然科学研究计划(2011A150023,2008B150018) (2011A150023,2008B150018)商丘师院重大项目培育计划(2011ZDPY02) (2011ZDPY02)

2-Ethoxycarbonyl-3,4-tetramethylenepyrrole prepared from cyclohexene through an improved twostep procedure was treated with excess lithium aluminum hydride at high temperature to give 2-methyl-3,4-tetramethylenepyrrole.Further condensation with protected 4-formylphenylboronic acid in the presence of trifluoroacetic acid as catalyst,followed by oxidation with 2,3-dichloro-5,6-dicyanobenzoquinone(DDQ) and treatment with triethylamine and boron trifluoride etherate,gives a novel exocyclic ring-fused borondipyrromethene(BDP) dye derivative substituted with phenylboronic ester subunit at the meso-position.The UV-Vis absorption titration and fluorescence titration measurements for BDP dye derivative were carried out to examine its responsibility to D-fructose,D-galactose,and D-glucose at specific pH.The influence of covalent interactions of BDP dye derivative with monosaccharides on its spectroscopic properties can be selectively recognized by both absorption and fluorescence spectra.By the nonlinear curve-fitting analysis of the fluorescence titration data,the association constants K_s of BDP derivative 1 with monosaccharide such as Dfructose,D-galactose,and D-glucose are 1045,445 and 130 L/mol,respectively.Thus BDP derivative 1 can be used as a sensitive and selective fluorescent probe for monosaccharides.Moreover,the sensing mechanism of the fluorescent probe was also preliminarily discussed.
- boron dipyrromethene dye,
- fluorescent probe,
- monosaccharide,
- fused exocyclic rings,
- phenylboronic acid
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