New benzotriazole-based D-A-D type solvatochromic dyes for water content detection in organic solvents

被引：35

作者：

Hou, Fang ^{[1
]}

Liu, Xiaolei ^{[1
]}

Hao, Xueying ^{[1
]}

Li, Guofei ^{[1
]}

Lu, Futai ^{[1
]}

Deng, Qiliang ^{[1
]}

机构：

[1] Tianjin Univ Sci & Technol, Coll Chem Engn & Mat Sci, Tianjin 300457, Peoples R China

来源：

DYES AND PIGMENTS | 2021年 / 195卷

基金：

中国国家自然科学基金;

关键词：

Fluorescence sensor; Water content; D-A-D; Benzotriazole; HIGHLY EFFICIENT; SENSING PLATFORM; CHARGE-TRANSFER; D CHROMOPHORES; FLUORESCENCE; SENSOR; PROBES;

D O I：

10.1016/j.dyepig.2021.109667

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Two new D-A-D structured organic dyes (LM1 and LM2) based on methoxy substituted triphenylamine (MeOTPA) as the electron donor, N-aryl benzotriazole as the electron acceptor have been designed and synthesized for water content detection in organic solvents. Both dyes exhibit large stoke shift with solvatochromic properties and display apparent fluorescence quenching upon the addition of different amount of water in organic solvents. Compared to LM1, LM2 with stronger electron-withdrawing acceptor fluorinated benzotriazole possesses red shifted absorption and fluorescence emission, enhanced intramolecular charge transfer (ICT) properties and stronger hydrogen-bonding interaction, resulting in a lower limit of detection (LOD) for water. The LODs in THF and 1,4-dioxane of LM2 are 0.009 % and 0.024 %, respectively, which indicates its great potential application in detecting water content in organic solvents.

引用

页数：9

共 38 条

[1] A Poly(9-Borafluorene) Homopolymer: An Electron-Deficient Polyfluorene with "Turn-On" Fluorescence Sensing of NH3 Vapor [J].

Adams, Ian A. ;

Rupar, Paul A. .

MACROMOLECULAR RAPID COMMUNICATIONS, 2015, 36 (14) :1336-1340

[2] Superiority of D-A-D over D-A type of organic dyes for the application in dye-sensitized solar cell [J].

Biswas, Santu ;

Pramanik, Anup ;

Ahmed, Tasnim ;

Sahoo, Suman Kalyan ;

Sarkar, Pranab .

CHEMICAL PHYSICS LETTERS, 2016, 649 :23-28

[3] Prompt responsive sensors for water detection in organic solvents [J].

Casalbore-Miceli, G. ;

Chen, Y. S. ;

Girotto, E. M. ;

Li, Y. ;

Rinaldi, A. W. ;

Yang, M. J. ;

Zanelli, A. .

SENSORS AND ACTUATORS B-CHEMICAL, 2006, 119 (02) :577-582

[4]

Chan J, 2012, NAT CHEM, V4, P973, DOI [10.1038/NCHEM.1500, 10.1038/nchem.1500]

[5] Covalent organic frameworks as a sensing platform for water in organic solvent over a broad concentration range [J].

Chen, Yujie ;

Zhang, Caiyun ;

Xie, Jiangyang ;

Li, Haijie ;

Dai, Wenjing ;

Deng, Qiliang ;

Wang, Shuo .

ANALYTICA CHIMICA ACTA, 2020, 1109 :114-121

[6] Optical determination of low-level water concentrations in organic solvents using fluorescent acridinyl dyes and dye-immobilized polymer membranes [J].

Citterio, D ;

Minamihashi, K ;

Kuniyoshi, Y ;

Hisamoto, H ;

Sasaki, S ;

Suzuki, K .

ANALYTICAL CHEMISTRY, 2001, 73 (21) :5339-5345

[7] Turn-On Luminescence Sensing and Real-Time Detection of Traces of Water in Organic Solvents by a Flexible Metal-Organic Framework [J].

Douvali, Antigoni ;

Tsipis, Athanassios C. ;

Eliseeva, Svetlana V. ;

Petoud, Stephane ;

Papaefstathiou, Giannis S. ;

Malliakas, Christos D. ;

Papadas, Ioannis ;

Armatas, Gerasimos S. ;

Margiolaki, Irene ;

Kanatzidis, Mercouri G. ;

Lazarides, Theodore ;

Manos, Manolis J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) :1651-1656

[8] NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist [J].

Fulmer, Gregory R. ;

Miller, Alexander J. M. ;

Sherden, Nathaniel H. ;

Gottlieb, Hugo E. ;

Nudelman, Abraham ;

Stoltz, Brian M. ;

Bercaw, John E. ;

Goldberg, Karen I. .

ORGANOMETALLICS, 2010, 29 (09) :2176-2179

[9] Lifetime-based fiber-optic water sensor using a luminescent complex in a lithium-treated Nafion™ membrane [J].

Glenn, SJ ;

Cullum, BM ;

Nair, RB ;

Nivens, DA ;

Murphy, CJ ;

Angel, SM .

ANALYTICA CHIMICA ACTA, 2001, 448 (1-2) :1-8

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

Guan, X. L. ;

Jia, T. M. ;

Zhang, D. H. ;

Zhang, Y. ;

Ma, H. C. ;

Lu, D. D. ;

Lai, S. J. ;

Lei, Z. Q. .

DYES AND PIGMENTS, 2017, 136 :873-880

← 1 2 3 4 →