Synthesis, Fluorescence Properties and Theoretical Calculations of Novel Stilbene Derivatives Based on 1,3,4-Oxadiazole Bearing Anthracene Core

Abstract

Two novel stilbene derivatives bearing anthracene core based on 1,3,4-oxadiazole were efficiently synthesized and characterized by (1)H-NMR, mass spectrometry and elemental analysis. The optical properties of the title compounds were investigated by UV-vis absorption and fluorescence emission spectra in different solvents. Chemical calculations were performed by density functional theory (DFT) at the (B3LYP)/6-31G* level. The results show the two compounds exhibit strong green fluorescence emission ranged from 489-493 nm, and the fluorescence quantum yield ranged from 0.78-0.92. Their HOMO and LUMO levels are (-5.44 eV, -2.25 eV) and (-5.45 eV, -2.28 eV), respectively. The influence of the solvent on the fluorescence intensities was also discussed.

1-Methyl-4-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]pyridinium 4-bromobenzenesulfonate monohydrate

“…(Chanawanno et al, 2010), anticancer (Belluti et al, 2010) and antioxidant (Frombaum et al, 2012) agents. In addition, some stilbenes also exhibit non-linear optical (Ruanwas et al, 2010) and fluorescent properties (Li et al, 2013). They are also generally used in the manufacturing industry as whitening agents (Hussain et al, 2009).…”

“…For bond-length data, see: Allen et al (1987). For applications of stilbene derivatives, see: Belluti et al (2010); Chanawanno et al (2010); Frombaum et al (2012); Hussain et al (2009); Jindawong et al (2005); Li et al (2013); Ruanwas et al (2010). For related structures, see: Chanawanno et al (2009); Fun et al (2011); Jindawong et al (2005).…”

2-[(E)-2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate monohydrate

“…For applications of stilbene derivatives, see: Chanawanno et al (2010); Frombaum et al (2012); Hussain et al (2009); Jindawong et al (2005); Kobkeatthawin et al (2009); Li et al (2013); Ruanwas et al (2010). For related structures, see, Chanawanno et al (2009); Chantrapromma et al (2013); Fun et al (2011).…”

“…For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986). Stilbene-based compounds have been reported to possess a wide range of biological activities including antibacterial (Chanawanno et al, 2010) and antioxidant (Frombaum et al, 2012) activities and also non-linear optical (Ruanwas et al, 2010) and fluorescent properties (Li et al, 2013). We have previously reported several crystal structures and applications of stilbene derivatives (Chanawanno et al, 2009;2010, Kobkeatthawin et al, 2009, Ruanwas et al, 2010.…”