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Acta Chimica Sinica >

2012 , Vol. 70 >Issue 18: 1987 - 1992

DOI: https://doi.org/10.6023/A12050237

Article

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

  • Hu Jinting ,
  • Liu Yang ,
  • Yang Kai ,
  • Shi Jianbing ,
  • Tong Bin ,
  • Zhi Junge ,
  • Dong Yuping
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  • a College of Chemistry, Beijing Institute of Technology, Beijing 100081;
    b College of Materials, Beijing Institute of Technology, Beijing 100081

Received date: 2012-05-25

  Online published: 2012-07-27

Supported by

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

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Abstract

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

Cite this article

Hu Jinting , Liu Yang , Yang Kai , Shi Jianbing , Tong Bin , Zhi Junge , Dong Yuping . Fabrication of Self-Assembled Monolayer Based on Phenylethynylbenzene and Fluorescent Probe Pyrene and Detecting for Nitroanilines[J]. Acta Chimica Sinica, 2012 , 70(18) : 1987 -1992 . DOI: 10.6023/A12050237

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