杯[4]芳烃的表面化学组装及其在气态四氢呋喃荧光传感薄膜创制中的应用

doi:10.7517/j.issn.1674-0475.2015.01.067

影像科学与光化学 ›› 2015, Vol. 33 ›› Issue (1): 67-76.DOI: 10.7517/j.issn.1674-0475.2015.01.067

杯[4]芳烃的表面化学组装及其在气态四氢呋喃荧光传感薄膜创制中的应用

马莹, 鱼春萌, 刘科, 蔡秀琴, 张少飞, 房喻

陕西师范大学化学化工学院应用表面与胶体化学教育部重点实验室, 陕西西安 710010

收稿日期:2014-10-08 修回日期:2014-11-19 出版日期:2015-01-15 发布日期:2015-01-15
通讯作者: 房喻
基金资助:
国家自然科学基金项目(91027017, 21273141)和高校创新研究团队项目(IRT1070) 资助

Surface Chemically Assembly of Calix[4]arene and Its Utilization in the Development of a Fluorescence Sensing Film for THF

MA Ying, YU Chunmeng, LIU Ke, CAI Xiuqin, ZHANG Shaofei, FANG Yu

Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710010, Shaanxi, P. R. China

Received:2014-10-08 Revised:2014-11-19 Online:2015-01-15 Published:2015-01-15

摘要/Abstract

摘要：

挥发性有机化合物(Volatile Organic Compounds,VOCs)是重要的大气污染物,严重地危害着人类健康.本文设计合成了一种末端携带反应活性硅氧烷基团的杯[4]芳烃衍生物,通过自组装和表面化学反应将其共价结合于玻璃基质表面,获得了一种杯[4]芳烃修饰玻璃基质.以此基质物理担载荧光活性物质——芘封端三聚噻吩(Py-3T),得到了一种对气相四氢呋喃具有"turn-on"及快速灵敏(26.7 μg/mL)响应特性的荧光传感薄膜.实验表明:除苯和甲苯之外,其它常见有机溶剂和化学物质蒸汽对该薄膜荧光发射基本没有影响.苯和甲苯也因响应程度小、响应速度慢而难以干扰测定过程.据此,可以预期该荧光薄膜有可能在THF气体传感上获得应用.

关键词: 杯[4]芳烃, 荧光传感薄膜, 化学自组装, 四氢呋喃

Abstract:

Volatile organic compounds (VOCs) are major components of atmospheric pollutants which are harmful to human being. In this work, a novel di-urea bridged calix[4]arene derivative ended with siloxane was designed and synthesized. The compound was then utilized for the modification of pre-cleaned glass plate surface, and in this way, a substrate with a layer of calix[4]arene was fabricated. Upon dip-coating a fluorescent compound, pyrenyl derivative of terthiophene (Py-3T), onto the substrate surface, a fluorescence "turn-on" film sensor for THF in vapor phase was developed. It was demonstrated that the film is highly sensitive to the presence of THF vapor (DL, 26.7 μg/mL), and the sensing is fast and reversible. With exception of benzene and toluene, other commonly found organic liquids and chemicals show little effect upon the sensing. It is believed that the film may have real-life uses in THF sensing.

Key words: calix[4]arene, fluorescence sensing film, chemical self-assembly, THF

马莹, 鱼春萌, 刘科, 蔡秀琴, 张少飞, 房喻. 杯[4]芳烃的表面化学组装及其在气态四氢呋喃荧光传感薄膜创制中的应用[J]. 影像科学与光化学, 2015, 33(1): 67-76.

MA Ying, YU Chunmeng, LIU Ke, CAI Xiuqin, ZHANG Shaofei, FANG Yu. Surface Chemically Assembly of Calix[4]arene and Its Utilization in the Development of a Fluorescence Sensing Film for THF[J]. Imaging Science and Photochemistry, 2015, 33(1): 67-76.

参考文献

[1] Tancrede M, Wilson R, Zeise L, Crouch E A C. The carcinogenic risk of some organic vapors indoors: a theoretical survey [J]. Atmospheric Environment, 1987, 21: 2187-2205.
[2] Molhave L. Indoor climate, air pollution, and human comfort [J]. Journal of Exposure Analysis and Environment Epidemiology, 1991, 1: 63-81.
[3] Huang C Y, Song M, Gu Z Y, Wang H F, Yan X P. Probing the adsorption characteristic of metal-organic framework MIL-101 for volatile organic compounds by quartz crystal microbalance [J]. Environmental Science and Technology, 2011, 45: 4490-4496.
[4] Viricelle J P, Pauly A, Mazet L, Brunet J, Bouvet M, Varenne C, Pijolat C. Selectivity improvement of semi-conducting gas sensors by selective filter for atmospheric pollutants detection [J]. Materials Science and Engineering C, 2006, 26: 186-195.
[5] Harbeck S, Emirik Õ F, Gürol I, Gürek A G, Õztürk Z Z, Ahsen V. Understanding the VOC sorption processes on fluoro alkyl substituted phthalocyanines using ATR FT-IR spectroscopy and QCM measurements [J]. Sensors and Actuators, B: Chemical, 2013, 176: 838 849.
[6] Pearce T C, Schiffman S S, Nagle H T, Gardner J W. Handbook of Machine Olfaction: Electronic Nose Technology [M]. Wiley-VCH, Weinheim, 2003.
[7] Rabolt J F, Santo R, Schlotter N E, Swalen J D. Integrated optics and raman scattering: molecular orientation in thin polymer films and langmuir-blodgett monolayers [J]. IBM Journal of Research and Development, 1982, 26: 209-216.
[8] Hillman A R, Loveday D C, Swann M J, Bruckenstein S, Wilde C P. Analytical applications of the electrochemical quartz crystal microbalance [J]. ACS Symposium Series, 1992, 487: 150-163.
[9] Sayago I, Fern ndez M J, Fontecha J L, Horrillo M C, Vera C, Obieta I, Bustero I. New sensitive layers for surface acoustic wave gas sensors based on polymer and carbon nanotube composites[J]. Sensors and Actuators, B:Chemical, 2012, 175: 67-72.
[10] Szmacinski H, Lakowicz J R. Lifetime-based sensing using phase-modulation fluorometry [J]. ACS Symposium Series, 1993, 538: 196-226.
[11] Basabe-Desmonts L, Reinhoudt D N, Crego-Calama M. Design of fluorescent materials for chemical sensing [J]. Chemical Society Review, 2007, 36: 993-1017.
[12] Ding L P, Liu Y, Cao Y, Wang L L, Xin Y H, Fang Y. A single fluorescent self-assembled monolayer film sensor with discriminatory power [J]. Journal of Materials Chemistry, 2012, 22: 11574-11582.
[13] Mansour M A, Connick W B, Lachicotte R J, Gysling H J, Eisenberg R. Linear chain Au(Ⅰ) dimer compounds as environmental sensors: a luminescent switch for the detection of volatile organic compounds [J]. Journal of the American Chemical Society, 1998, 120: 1329-1330.
[14] Kimura M, Yokokawa M, Sato S, Fukawa T, Mihara T. Volatile organic compound sensing by gold nanoparticles capped with calix
[4] arene ligand [J]. Chemistry Letter, 2011, 40: 1402-1404.
[15] Koshets I A, Kazantseva Z I, Shirshov Y M, Cherenok S A, Kalchenko V I. Calixarene films as sensitive coatings for QCM-based gas sensors [J]. Sensors and Actuators, B: Chemical, 2005, 106: 177-181.
[16] Topliss S M, James S W, Davis F, Higson S P J, Tatam R P. Optical fibre long period grating based selective vapour sensing of volatile organic compounds [J]. Sensors and Actuators, B: Chemical, 2010, 143: 629-634.
[17] Holloway A F, Nabok A, Hashim A A, Penders J. The use of calixarene thin films in the sensor array for VOCs detection and olfactory navigation [J]. Sensors & Transducers Journal, 2010, 113: 71-81.
[18] Ding L P, Fang Y. Chemically assembled monolayers of fluorophores as chemical sensing materials [J]. Chemical Society Reviews, 2010, 39: 4258-4273.
[19] Sidharam P P, Luc S, Antonius T M M, Han Z. Covalent surface modification of oxide surfaces [J]. Angewandte Chemie International Edition, 2014, 53: 6322-6356.
[20] Liu T H, Ding L P, Zhao K R, Wang W L, Fang Y. Single-layer assembly of pyrene end-capped terthiophene and its sensing performances to nitroaromatic explosives [J]. Journal of Materials Chemistry, 2012, 22: 1069-1077.
[21] Liu T H, Zhao K R, Liu K, Ding L P, Yin S W, Fang Y. Synthesis, optical properties and explosive sensing performances of a series of novel π-conjugated aromatic end-capped oligothiophenes [J]. Journal of Hazardous Materials, 2013, 246-247: 52-60.

杯[4]芳烃的表面化学组装及其在气态四氢呋喃荧光传感薄膜创制中的应用

Surface Chemically Assembly of Calix[4]arene and Its Utilization in the Development of a Fluorescence Sensing Film for THF

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 0

编辑推荐

Metrics

本文评价