Abstract
In this study a new 2,6-distyryl naphthalene [2-((4-((E)-2-(6-((E)-2,4-bis(methylsulfonyl)styryl)naphthalen-2-yl)vinyl)phenyl)(ethyl)amino)ethan-1-ol; ASDSN] was synthesized successfully using Heck chemistry as the main reaction. The ASDSN compound is a donor–pi–acceptor (D–π–A) conjugated system with amino as electron donating and sulfonyl as electron withdrawing groups. The UV-vis absorption of ASDSN was observed in the range of 403–417 nm with high molar extinction coefficients (ε = 15 300–56 200 M−1 cm−1) in some different solvents. This new fluorescent 2,6-distyryl naphthalene compound emits in the yellow region of the visible spectrum (557 nm) with Stokes shifts of 5930 cm−1. ASDSN is a pH-responsive fluorescence compound that shows yellow fluorescence in neutral form and blue fluorescence in the protonated form. A white light emission (WLE) for the chromophore was observed at pH = 3.0. The ASDSN chromophore presented a satisfactory white light quantum yield (Φ) of 13% which was desirable for producing white light emitting devices. Density functional theory (DFT) and time-dependent (TD)-DFT were applied to study structural and electronic properties of the chromophore.
Highlights
Organic molecules that possess intramolecular charge transfer (ICT) character are important in a large number of areas, such as organic solar cells, polarity probes and nonlinear optics.[7,8]
We showed that the ASDSN chromophore experience a hypsochromic shi from yellow to blue with the variation of pH and emit white light at pH 1⁄4 3
The Heck reaction using a palladium-catalyzed process was employed as a main organic transformation for the synthesis of the ASDSN chromophore (Scheme 1)
Summary
The synthesis of uorophores incorporating distyrylbenzene pconjugated systems has attracted considerable attention because of their high potential applications in optoelectronic and sensory devices as well as uorescent probes in medical utilization and in organic light-emitting diodes.[1,2,3,4,5,6] On the other hand, organic molecules that possess intramolecular charge transfer (ICT) character are important in a large number of areas, such as organic solar cells, polarity probes and nonlinear optics.[7,8]Donor–p–acceptor (D–p–A; where D is an electron-donating group, A is an electron-accepting group, and p is a conjugating moiety) systems with different con gurations have been extensively developed because their absorption spectra and energy gaps can be readily tuned by controlling the ICT character using different electron-donor and electron-acceptor groups. Paper for detecting metal ions.[17,18,19] substantial shi s in the absorption and emission of amino-functionalized stilbenes are observed upon protonation, representing pH-sensory capability of these materials.[20] In other words, they are halochromic chromophores with tunable uorescence through regulation of pH.
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