Synthesis, sensor activity and logic behaviour of a novel bichromophoric system based on rhodamine 6G and 1,8-naphthalimide

被引：57
作者：
Georgiev, Nikolai I. [1 ]
Dimitrova, Margarita D. [1 ]
Asiri, Abdullah M. [2 ,3 ]
Alamry, Khalid 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, CEAMR, Jeddah 21589, Saudi Arabia
来源：
DYES AND PIGMENTS | 2015年 / 115卷
基金：
美国国家科学基金会;
关键词：
1,8-Naphthalimide/Rhodamine 6G conjugate; Fluorescence resonance energy transfer (FRET); Photoinduced electron transfer (PET); Internal charge transfer (ICT); OR and INHIBIT logic gates; Two output combinatorial logic circuit; PHOTOINDUCED ELECTRON-TRANSFER; FLUORESCENT PH PROBE; PHOTOPHYSICAL PROPERTIES; LIVING CELLS; METAL-IONS; HG2+; CHEMOSENSOR; DESIGN; PET; GATES;
D O I：
10.1016/j.dyepig.2015.01.001
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A novel fluorescence sensing system based on rhodamine 6G and 1,8-naphthalimide fluorophores was synthesized and investigated. The system was designed as a wavelength-shifting bichromophoric molecule where the 1,8-naphthalimide moiety is an energy "donor" capable of absorbing light and efficiently transferring the energy to a focal Rhodamine 6G "acceptor". Furthermore, the 1,8-naphthalimide unit was configured on the "fluorophore-spacer-receptor" format. Thus, the distinguishing features of fluorescence resonance energy transfer systems were successfully combined with the properties of photoinduced electron transfer and classical ring-opening sensor systems. The synthesized compound shows excellent signalling properties towards protons as well as Cu2+ and Hg2+ over the representative metal ions. Due to the remarkable fluorescence changes in the presence of protons, Cu2+ and Hg2+ ions the novel system is able to act as a two output combinatorial logic circuit with three chemical inputs. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：172 / 180
页数：9
相关论文
共 71 条
[1]   Synthesis and steady-state photophysical properties of dye-labeled dendrimers having novel oligothiophene cores:: A comparative study [J].
Adronov, A ;
Malenfant, PRL ;
Fréchet, JMJ .
CHEMISTRY OF MATERIALS, 2000, 12 (05) :1463-1472
[2]   An integrated system of pyrene and rhodamine-6G for selective colorimetric and fluorometric sensing of mercury(II) [J].
Ahamed, B. Nisar ;
Ghosh, Pradyut .
INORGANICA CHIMICA ACTA, 2011, 372 (01) :100-107
[3]   A ratiometric rhodamine-naphthalimide pH selective probe built on the basis of a PAMAM light-harvesting architecture [J].
Alamry, Khalid A. ;
Georgiev, Nikolai I. ;
El-Daly, Samy Abdullah ;
Taib, Layla A. ;
Bojinov, Vladimir B. .
JOURNAL OF LUMINESCENCE, 2015, 158 :50-59
[4]   A highly selective ratiometric fluorescent pH probe based on a PAMAM wavelength-shifting bichromophoric system [J].
Alamry, Khalid A. ;
Georgiev, Nikolai I. ;
El-Daly, Samy Abdullah ;
Taib, Layla A. ;
Bojinov, Vladimir B. .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2015, 135 :792-800
[5]   All-photonic molecular half-adder [J].
Andreasson, Joakim ;
Straight, Stephen D. ;
Kodis, Gerdenis ;
Park, Choong-Do ;
Hambourger, Michael ;
Gervaldo, Miguel ;
Albinsson, Bo ;
Moore, Thomas A. ;
Moore, Ana L. ;
Gust, Devens .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) :16259-16265
[6]   Smart molecules at work-mimicking advanced logic operations [J].
Andreasson, Joakim ;
Pischel, Uwe .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :174-188
[7]   Durable diagnosis of seminal vesicle and sexual gland diseases using the nano optical sensor thin film Sm-doxycycline complex [J].
Attia, M. S. ;
Youssef, A. O. ;
El-Sherif, R. H. .
ANALYTICA CHIMICA ACTA, 2014, 835 :56-64
[8]  
Bojinov V., 2011, J U CHEM TECHNOL MET, V46, P3
[9]   Synthesis and photophysical properties of fluorescence sensing ester- and amidoamine-functionalized 1,8-naphthalimides [J].
Bojinov, Vladimir B. ;
Georgiev, Nikolai I. ;
Nikolov, Peter S. .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2008, 193 (2-3) :129-138
[10]   A novel blue fluorescent 4-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)-1,8-naphthalimide pH chemosensor based on photoinduced electron transfer [J].
Bojinov, Vladimir B. ;
Simeonov, Danail B. ;
Georgiev, Nikolai I. .
DYES AND PIGMENTS, 2008, 76 (01) :41-46
12345678