Synthesis, sensor activity, and logic behavior of a highly water-soluble 9,10-dihydro-7H-imidazo[1,2-b]benz[d,e]isoqionolin-7-one dicarboxylic acid

被引:26
作者
Georgiev, Nikolai I. [1 ]
Lyulev, Mihail P. [1 ]
Alamry, Khalid A. [2 ]
El-Daly, Samy Abdullah [2 ,3 ]
Taib, Layla A. [2 ]
Bojinov, Vladimir B. [1 ,2 ]
机构
[1] Univ Chem Technol & Met, Dept Organ Synth, BU-1756 Sofia, Bulgaria
[2] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia
[3] King Abdulaziz Univ, Ctr Excellence Adv Mat Res CEAMR, Jeddah 21589, Saudi Arabia
关键词
Naphthalimide derivative; Internal charge transfer (ICT); Photoinduced electron transfer (PET); Selective pH sensing in 100% aqueous media; AND; XOR; XNOR; and INH logic gates; Magnitude digital comparator and halfadder; PHOTOINDUCED ELECTRON-TRANSFER; FLUORESCENT MOLECULAR SENSORS; LUMINESCENT SENSORS; RHODAMINE; 6G; KEYPAD LOCK; PH; DESIGN; 1,8-NAPHTHALIMIDE; CHEMOSENSOR; NAPHTHALIMIDE;
D O I
10.1016/j.jphotochem.2014.09.013
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The design, synthesis, and sensor activity of a novel highly water-soluble 9,10-dihydro-7H-imidazo[1,2-b] benz[d,e]isoqionolin-7-one derivative are reported. The changes in the photophysical properties of the compound as a function of pH were investigated in 100% aqueous medium. Novel compound manifests ratiometric "off-on-off' pH sensor activity. Due to the two different "off"-states, it is able to execute the logical functions AND and XOR as well as INH and XNOR and as such, to act as a half-adder and a magnitude digital comparator, respectively. The synthesized compound shows excellent selectivity toward protons over the representative metal ions in ammonia/ammonium chloride buffer (pH 10) and HEPES (pH 7.3) solutions. The high water solubility and excellent pH selectivity and sensitivity of the probe may be beneficially for monitoring pH variations in complex samples. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:31 / 38
页数:8
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