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

doi:10.6023/A12050237

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

Article

基于苯炔苯及荧光探针芘自组装单分子膜的制备及苯胺检测

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

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 Jinting^a, Liu Yang^b, Yang Kai^a, Shi Jianbing^b, Tong Bin^b, Zhi Junge^a, Dong Yuping^b

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 http://sioc-journal.cn. Project supported by the National Natural Science Foundation of China (Nos. 20504005, 21074012).

1. Fabrication of Self-Assembled Monolayer Based on Phenylethynylbenzene and Fluorescent Probe Pyrene and Detecting for Nitroanilines.PDF(251KB)

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

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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.

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基于苯炔苯及荧光探针芘自组装单分子膜的制备及苯胺检测

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

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