Design, synthesis and fluorescence analysis of potential fluorescent markers based on cardanol and glycerol. (June 2017)

• Record Type: Journal Article
• Authors: Braga, Felipe C.; Prasad, Avvari N.; da Silva Gomes, Roberto; do Nascimento, Valter A.; Oliveira, Samuel L.; Caires, Anderson R.L.; de Lima, Dênis P.; Beatriz, Adilson
• Is Part Of: Dyes and pigments. Volume 141(2017)
• Page Start: 235
• Page End: 244
• Publication Date: 2017-06
• Subjects: Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2017.02.032
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: We report the synthesis and fluorescent properties of 1, 4-disubstituted-1, 2, 3-triazoles (1a-c ) based on pollutant wastes and by-products from the cashew and biodiesel industries as a design for fluorescent markers. The triazoles were synthesized in four steps; catalytic hydrogenation of cardanol, reaction with epichlorohydrin, azide substitution and/or epoxide opening and, Cu catalyzed click-chemistry of the azide with the ethynylanilines (6a-c ). This procedure is a potential alternative to make fluorescent markers since it affords the intermediates in high yields, enabling one to produce the products in good quantities. Moreover, triazolazobenzenes (8a-c ) were prepared by azo coupling of the trizoles (1a-c ) with phenol to give a new option of dyes. Evaluation of the fluorescent properties of the achieved compounds showed that all triazole derivatives displayed good fluorescence emissions in the range of 325–400 nm, with a maximum of fluorescence intensity at around 350 nm when excited between 225 and 300 nm; besides, the para -triazolaniline exhibited a dual fluorescence emission, presenting an additional emission band in the blue range (400–500 nm). Graphical abstract: We provide an alternative to use cardanol and glycerol as building blocks to produce six structurally, amphiphilic molecules. The meta -triazolaniline (1b ) presented a high fluorescent signal at low concentration (4 ppm), revealing to be the best candidate for a fuel marker. Highlights: We provide an alternative to use cardanol and glycerol as building blocks to produce novel fluorescent amphiphilic molecules. para -triazolaniline exhibited a dual fluorescence emission, presenting an additional emission band in the blue range. meta -triazolaniline presented a high fluorescent signal at low concentration.