Chem. J. Chinese Universities ›› 2009, Vol. 30 ›› Issue (9): 1809.

• Articles • Previous Articles     Next Articles

Synthesis of a Novel Amphiphile Containing Both Phenylboronic Acid and Naphthalene and Preparation of the Fluorescent Vesicular Sensor

LI Guang-Quan, ZHANG Yu-Jian, ZHANG Xiao, HE Zhen-Feng, CHEN Yun-Xia, LI Guo-Wen*   

  1. State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, China
  • Received:2008-10-27 Online:2009-09-10 Published:2009-09-10
  • Contact: LI Guo-Wen. E-mail: lgw@jlu.edu.cn
  • Supported by:

    国家自然科学基金(批准号: 20674025, 20874037)资助.

Abstract:

A novel amphiphile containing two functional groups of both naphthalene and phenylboronic acid, p-[(5-dodecyloxy-1-oxy) naphthalene] methyl-phenylboronic acid(DNMPBA), was synthesized. The amphiphile was self-organized into vesicles in the selective solution of THF/water(φ=0.6) buffered at pH=6.86. The Tc of the vesicles from crystal to liquid crystal is 56.8 ℃. Addition of saccharides to the vesicular solution, the fluorescent intensities of naphthalene in DNMPBA vesicles centered at 345 nm increase dramatically with increasing concentration of saccharides. The changed tendency for fluorescent intensities of the DNMPAB vesicles with saccharides is similar to the other systems reported in literature to favor the binding with fructose over glucose and maltose. The increase of fluorescence intensity is ascribed to boronic ester formation which might diminish the photoinduced electron transfer(PET) progress to induce fluorescence retrieval and, therefore, increase the fluorescence intensity. The vesicular sensor through the interactions between boronic acid and saccharides displayed at a biomimetic membrane interface can be detected by means of fluorescence intensities. The results suggest that the fluorescent vesicles might be used as biosensors to determine saccharides.

Key words: Amphiphile; Sensor; Vesicle; Fluorescence spectrum

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