Acta Chimica Sinica ›› 2012, Vol. 70 ›› Issue (18): 1987-1992.DOI: 10.6023/A12050237 Previous Articles    



胡金婷a, 刘暘b, 杨凯a, 石建兵b, 佟斌b, 支俊格a, 董宇平b   

  1. a 北京理工大学化学学院 北京 100081;
    b 北京理工大学材料学院 北京 100081
  • 投稿日期:2012-05-25 发布日期:2012-07-27
  • 通讯作者: 支俊格,董宇平
  • 基金资助:

    项目受国家自然科学基金(Nos. 20504005, 21074012)资助.

Fabrication of Self-Assembled Monolayer Based on Phenylethynylbenzene and Fluorescent Probe Pyrene and Detecting for Nitroanilines

Hu Jintinga, Liu Yangb, Yang Kaia, Shi Jianbingb, Tong Binb, Zhi Jungea, Dong Yupingb   

  1. a College of Chemistry, Beijing Institute of Technology, Beijing 100081;
    b College of Materials, Beijing Institute of Technology, Beijing 100081
  • Received:2012-05-25 Published:2012-07-27
  • Supported by:

    Supporting information for this article is available free of charge via the Internet at Project supported by the National Natural Science Foundation of China (Nos. 20504005, 21074012).

Self-Assembled monolayers (SAMs), a new type of organic ultra-thin films, show a lot of interesting properties in chemistry, physics, optics and electronic transport, and have potential application in biomaterials, nanoelectro-mechanical systems, sensors, and so on. In this paper, a full-conjugated unit-containing SAM ended with a functional amino group (NH2) was fabricated by self-assembly and using a light-sensitive diazonium-containing compound 4-(4-amino phenylene ethynyl) benzenic diazonium salt (APEB-N2+). The APEB-N2+ was easily deposited on a pre-treated quartz substrate with negative charges by electrostatic interaction and then grafted on the surface of a quartz substrate through covalent bond after the decomposition of diazonium group under UV irradiation, and a stable SAM based on phenylethynylbenzene was obtained. Furthermore, based on the reactivity of the functional group NH2, the fluorescent probe pyrene is anchored on the surface of the full-conjugated SAM through two approaches:amidation reaction between amino group on the SAM and carboxyl group of 1-pyrenebutyric acid, and self-assembly of N2+, which is transferred from NH2 on SAM, and electronegative COO- of 1-pyrenebutyric acid in basic aqueous solution. The obtained ultra-thin films with fluorescence probe pyrene exhibit luminescent property because of the emission of excimer of pyrene chromophore, which is mainly due to the formation of the g-g conformation of pyrene for the induction effect of the full-conjugated SAM. The electron-acceptor nitroanilines (NAs) can quench the fluorescence of the obtained ultra-thin film because of electron and energy transfer between the electron-rich pyrene and NAs. The fluorescence quenching varies obviously for the different isomers of NA, and the quenching efficiency decreases according to the sequence of p-NA, o-NA, m-NA, because the electronic effect varies obviously when the relative position of electron withdrawing group NO2 and donating group NH2 of NA are different. The fluorescence of the ultra-thin film decreases with the increasing of the NA concentration.

Key words: conjugated self-assembled monolayer, pyrene, photochemistry of diazonium salts, luminescent property, detection of nitroaniline