A new solvatochromic linear π-conjugated dye based on phenylene(poly)ethynylene as supersensitive low-level water detector in organic solvents

被引:35
作者
Guan, X. L. [1 ]
Jia, T. M. [1 ]
Zhang, D. H. [1 ]
Zhang, Y. [1 ]
Ma, H. C. [1 ]
Lu, D. D. [1 ]
Lai, S. J. [2 ]
Lei, Z. Q. [1 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Key Lab Ecoenvironm Related Polymer Mat, Minist Educ,Key Lab Polymer Mat,Minist Gansu Prov, Lanzhou 730070, Gansu, Peoples R China
[2] Lanzhou Univ Arts & Sci, Sch Chem Engn, Lanzhou 730000, Gansu, Peoples R China
基金
高等学校博士学科点专项科研基金; 中国国家自然科学基金;
关键词
pi-conjugated dye; Phenylene(poly)ethynylene; Solvatochromic sensor; Water detector; Organic solvents; TRACE WATER; FLUORESCENT; HUMIDITY; POLARITY; PROBES;
D O I
10.1016/j.dyepig.2016.09.055
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel class of phenylene-(poly)ethynylene-based dye Sensor 1 with remarkable properties of solvatochromism has been designed and synthesized. A long, coplanar and asymmetry electron-rich pi-conjugated structure endows Sensor 1 with maximum solvatochromic effect by intramolecular charge-transferstates (ICT). More importantly, The dye is found to serve as supersensitive fluorescent indicator for the quantitative detection of low-level water content in five common organic solvents with low detection limits. Furthermore, the development of easy-to-prepare test papers provides a convenient and reliable approach to qualitatively monitor water in organic solvents by naked eye. Results in this work not only provide a successful molecular design concept of the novel sensitive solvatochromic dye sensor for water in organic solvents, but also develop practical applications of the linear pi-conjugated molecule bearing phenylene-(poly)ethynylene in chemosensor field. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:873 / 880
页数:8
相关论文
共 39 条
  • [1] A Poly(9-Borafluorene) Homopolymer: An Electron-Deficient Polyfluorene with "Turn-On" Fluorescence Sensing of NH3 Vapor
    Adams, Ian A.
    Rupar, Paul A.
    [J]. MACROMOLECULAR RAPID COMMUNICATIONS, 2015, 36 (14) : 1336 - 1340
  • [2] A new definition of cavities for the computation of solvation free energies by the polarizable continuum model
    Barone, V
    Cossi, M
    Tomasi, J
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (08) : 3210 - 3221
  • [3] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
    BECKE, AD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
  • [4] Synthesis and Photophysical Properties of a Series of Cyclopenta[b]naphthalene Solvatochromic Fluorophores
    Benedetti, Erica
    Kocsis, Laura S.
    Brummond, Kay M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) : 12418 - 12421
  • [5] Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants
    Bradley, D.
    Williams, G.
    Lawton, Michelle
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) : 8351 - 8354
  • [6] Negative solvatochromism of merocyanine dyes: Application as water content probes for organic solvents
    Cha, Sunyoung
    Choi, Myung Gil
    Jeon, Hye Rim
    Chang, Suk-Kyu
    [J]. SENSORS AND ACTUATORS B-CHEMICAL, 2011, 157 (01): : 14 - 18
  • [7] Chan J, 2012, NAT CHEM, V4, P973, DOI [10.1038/nchem.1500, 10.1038/NCHEM.1500]
  • [8] Humidity-sensitive optode membrane based on a fluorescent dye immobilized in gelatin film
    Choi, MMF
    Tse, OL
    [J]. ANALYTICA CHIMICA ACTA, 1999, 378 (1-3) : 127 - 134
  • [9] Highly sensitive determination of low-level water content in organic solvents using novel solvatochromic dyes based on thioxanthone
    Ding, Li
    Zhang, Zhiyun
    Li, Xin
    Su, Jianhua
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (66) : 7319 - 7321
  • [10] Solvatochromic Fluorescence of Piperazine-Modified Bipyridazines for an Organic Solvent-Sensitive Film
    Do, Jaekwon
    Huh, June
    Kim, Eunkyoung
    [J]. LANGMUIR, 2009, 25 (16) : 9405 - 9412