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林产化学与工业

林产化学与工业 ›› 2019, Vol. 39 ›› Issue (1): 61-66.doi: 10.3969/j.issn.0253-2417.2019.01.009

• 研究报告 • 上一篇    下一篇

含双萘的脱氢枞酸三芳胺化合物的合成及光谱性能

檀贯妮1,高亚楠1,高宏1,2,*(),商士斌1,2,宋湛谦1,2   

  1. 1. 中国林业科学研究院 林产化学工业研究所; 生物质化学利用国家工程实验室; 国家林业局 林产化学工程重点开放性实验室; 江苏省 生物质能源与材料重点实验室，江苏 南京 210042
    2. 中国林业科学研究院 林业新技术研究所，北京 100091
  • 收稿日期:2018-09-20 出版日期:2019-02-25 发布日期:2019-03-14
  • 通讯作者: 高宏 E-mail:gaoh2188@hotmail.com
  • 作者简介:檀贯妮(1994—)，女，安徽安庆人，硕士生，从事松香精细化利用研究
  • 基金资助:
    国家自然科学基金资助项目(31670576)

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:
    国家自然科学基金资助项目(31670576)

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摘要：

以歧化松香为原料先制得脱氢枞酸，然后通过对脱氢枞酸进行酯化、溴代、硝化、加氢还原、C—N偶联等方法合成了一种含双萘的脱氢枞酸三芳胺化合物——13-[N, N-双(α-萘)]胺基-脱异丙基脱氢枞酸甲酯，并用IR、1H NMR、13C NMR和MS等手段对其结构进行表征。研究了化合物在甲醇、二氧六环、四氢呋喃、二氯甲烷和环己烷5种不同极性溶剂中的紫外吸收和荧光发射特征，以及化合物的荧光寿命和量子产率，结果显示：化合物有3个紫外吸收峰，在甲醇、二氧六环和环己烷中，第一个吸收峰在218 nm处，而在四氢呋喃和二氯甲烷中吸收峰有较大红移，且吸光度有较大不同；在265、342 nm处的两个吸收峰，不同溶剂中的吸收波长一致，且吸光度相差不大；在这5种溶剂中，化合物在甲醇中发射波长最大(448 nm)，荧光强度最小，在环己烷中发射波长最小(405 nm)，而荧光强度最大，在二氧六环、四氢呋喃和二氯甲烷溶液中，随着溶剂极性减小，发射波长依次增大；化合物有明显的溶致变色效应。化合物在甲醇溶液中的荧光寿命为3.72 ns,量子产率为8.32%。

关键词: 脱氢枞酸三芳胺, 双萘, 合成, 光谱性能

Abstract:

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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