脱氢枞酸三芳胺基D-π-A型荧光化合物的光谱性能及应用

doi:10.3969/j.issn.0253-2417.2020.04.011

林产化学与工业 ›› 2020, Vol. 40 ›› Issue (4): 79-85.doi: 10.3969/j.issn.0253-2417.2020.04.011

脱氢枞酸三芳胺基D-π-A型荧光化合物的光谱性能及应用

高亚楠^1,²,高宏^1,^3,*(),商士斌^1,³,宋湛谦^1,³

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; 国家林业和草原局林产化学工程重点实验室; 江苏省生物质能源与材料重点实验室, 江苏南京 210042
2. 南京林业大学江苏省林业资源高效加工利用协同创新中心, 江苏南京 210037
3. 中国林业科学研究院林业新技术研究所, 北京 100091

收稿日期:2020-04-23 出版日期:2020-08-28 发布日期:2020-08-21
通讯作者: 高宏 E-mail:gaoh2188@hotmail.com
作者简介:高亚楠(1996-),女,山西临汾人,硕士生,从事天然资源化学与利用的研究
基金资助:
国家自然科学基金资助项目(31670576)

Spectra Properities and Application of Dehydroabietic Acid Triarylamine Based D-π-A Type Fluorescent Compound

Yanan GAO^1,²,Hong GAO^1,^3,*(),Shibin SHANG^1,³,Zhanqian SONG^1,³

1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China
3. Research Institute of Forestry New Technology, CAF, Beijing 100091, China

Received:2020-04-23 Online:2020-08-28 Published:2020-08-21
Contact: Hong GAO E-mail:gaoh2188@hotmail.com

摘要/Abstract

摘要：

以脱氢枞酸为原料通过酯化、溴代、C-N偶联的方法合成脱氢枞酸三芳胺（b），再以溴代、C-C偶联等方法合成了脱氢枞酸三芳胺基D-π-A化合物2-异氰基-3-（5-（4-（（脱氢枞酸甲酯基）（4-甲氧基苯基）氨基）苯基）-2-噻吩基）丙烯酸（DTPA-I），研究了它的紫外吸收光谱和荧光发射光谱，并作为荧光探针用于检测极性有机溶剂中的水含量。研究结果表明：与化合物b比较，DTPA-I的紫外吸收光谱出现新的吸收峰（λ_abs，max=474 nm），荧光发射波长明显红移（λ_em，max=603 nm）；DTPA-I在不同的极性溶剂中的紫外吸收波长和荧光发射波长发生明显的位移，吸光度与荧光强度均发生变化，化合物具有明显的溶致变色效应。在0~1%的范围内，DTPA-I的荧光强度随着二氧六环、DMSO和DMF溶液中的水含量的增加呈线性降低，对二氧六环中水的检出限低至0.089%。

关键词: 脱氢枞酸三芳胺, D-π-A型化合物, 溶致变色效应, 检测

Abstract:

Dehydroabietic acid-based triarylamine(b) was synthesized via esterification, bromination, and C-N coupling, using dehydroabietic acid as starting material, then a D-π-A type compound (DTPA-I) with dehydroabietic acid-based triarylamine was synthesized by bromination, and C-C coupling. The ultraviolet absorption spectrum and fluorescence emission spectrum of DTPA-I were studied and it was also used as fluorescent probe to detect the water content in polar organic solvents. The results showed that compound DTPA-I showed a new absorption peak with the maximum adsorption wavelength of 474 nm in the UV absorption spectrum and its maximum wavelength of fluorescence emission red-shifted from 374 to 603 nm, compared with compound b; the maximum absorption wavelength and fluorescence emission wavelength of DTPA-I in different polar solvents had big shift, and the absorbance and fluorescence intensity were also different, which indicated the compound had significant solvatochromism effect. When DTPA-I was used as fluorescent probe to detect water content in solvents dioxane, DMSO and DMF, the fluorescence intensity of DTPA-I linearly decreased with the increase of concentration of water in solvents.The detection limit for water content in dioxane was as low as 0.089%.

Key words: dehydroabietic acid-based triarylamine, D-π-A compound, solvatochromism, detection

中图分类号:

TQ351
O657.3

高亚楠,高宏,商士斌,宋湛谦. 脱氢枞酸三芳胺基D-π-A型荧光化合物的光谱性能及应用[J]. 林产化学与工业, 2020, 40(4): 79-85.

Yanan GAO,Hong GAO,Shibin SHANG,Zhanqian SONG. Spectra Properities and Application of Dehydroabietic Acid Triarylamine Based D-π-A Type Fluorescent Compound[J]. Chemistry and Industry of Forest Products, 2020, 40(4): 79-85.

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脱氢枞酸三芳胺基D-π-A型荧光化合物的光谱性能及应用

Spectra Properities and Application of Dehydroabietic Acid Triarylamine Based D-π-A Type Fluorescent Compound

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