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Chemistry and Industry of Forest Products ›› 2019, Vol. 39 ›› Issue (1): 61-66.doi: 10.3969/j.issn.0253-2417.2019.01.009

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Synthesis and Spectra Performance of Dehydroabietic Acid-based Triarylamine with Double Naphthalenes

Guanni TAN1,Yanan GAO1,Hong GAO1,2,*(),Shibin SHANG1,2,Zhanqian SONG1,2   

  1. 1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key and Open Lab. of Forest Chemical Engineering, SFA; Key Lab.of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
    2. Research Institute of Forestry New Technology, CAF, Beijing 100091, China
  • Received:2018-09-20 Online:2019-02-25 Published:2019-03-14
  • Contact: Hong GAO E-mail:gaoh2188@hotmail.com
  • Supported by:


A novel dehydroabietic acid-based triarylamine compound with two naphthalene was synthesized via esterification, bromation, nitration, hydrogenation reduction and C—N cross-coupling with the starting material dehydroabietic acid, which was obtained with disproportionated rosin as raw material, its structure was characterized by IR、1H NMR、13C NMR and mass spectrometry. The absorption spectra and fluorescent spectra of the compound in 5 kinds solvents with different polority were studied. The compound had three absorption peaks, the first adsorption peaks of compouds in methanol, dioxane and cyclohexane solvents were at 218 nm, the adsorption peaks showed red shift in tetrahydrofuran and dichloromethane solvents, and the absorbance were different; however, the absorption wavelengths were the same and the absorbance had little difference at 265 and 342 nm. Fluorescent emission wavelengths and intensities of title compound exsited marked difference in different polarity solvents, the emission wavelength was the biggest(448 nm), but the intensity was the smallest in bigger polority methanol; on the contrary, the emission wavelength was the smallest(405 nm) but the intensity was the biggest in smaller polarity cyclohexane solution; however, the emission wavelength increased gradually in dioxane, tetrahydrofuran and dichloromethane solutions with polarity decreasing. The differences in UV absorption spectra and fluorescence emission spectra of compound in different polar solvents indicated that it had significant solvatochromism effect. The fluorescence lifetime and quantum efficiency of compound in methanol were 3.72 ns and 8.32%.

Key words: dehydroabietic acid-based triarylamine, double naphthalene, synthesis, spectra performance

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