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林产化学与工业 ›› 2022, Vol. 42 ›› Issue (3): 10-18.doi: 10.3969/j.issn.0253-2417.2022.03.002

• 研究报告 • 上一篇    下一篇

脱氢枞酸三芳胺基丙烯腈化合物的合成及其光物理性能研究

高亚楠1,2,3, 窦立薇1,3, 宋杰4, 高宏1,3,*(), 商士斌1,3, 宋湛谦1,3   

  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
    4. 密歇根大学弗林特分校 化学与生物化学系,美国 弗林特 48502
  • 收稿日期:2021-02-06 出版日期:2022-06-28 发布日期:2022-07-04
  • 通讯作者: 高宏 E-mail:gaoh2188@hotmail.com
  • 作者简介:高宏,研究员,硕士生导师,主要从事天然资源化学与利用的研究;E-mail:gaoh2188@hotmail.com
    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)

Dehydroabietic Acid Triarylamine-based Acrylonitrile Compounds: Synthesis and Photophysical Properties

Yanan GAO1,2,3, Liwei DOU1,3, Jie SONG4, Hong GAO1,3,*(), Shibin SHANG1,3, Zhanqian SONG1,3   

  1. 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
    4. Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint 48502, USA
  • Received:2021-02-06 Online:2022-06-28 Published:2022-07-04
  • Contact: Hong GAO E-mail:gaoh2188@hotmail.com

摘要:

以5-脱氢枞酸三苯胺-噻吩-2-甲醛与3,5-双(三氟甲基)苯乙腈为原料,分别在常温和加热回流的条件下反应,得到2个脱氢枞酸三芳胺基丙烯腈化合物:甲基(Z)-6-((4-(5-(2-(3, 5-双(三氟甲基)苯基)-2-氰基乙烯基)噻吩-2-基)苯基)(4-甲氧基苯基)氨基)-7-异丙基-1, 4a-二甲基-1, 2, 3, 4, 4a, 9, 10, 10a-八氢菲-1-羧酸盐(2)和二甲基6, 6'-(((1-氰基乙烯-1, 2-二基)双(噻吩-5, 2-二基))双(4, 1-苯撑)双(4-甲氧基苯基)氮杂二烯基)(E)-双(7-异丙基-1, 4a-二甲基-1, 2, 3, 4, 4a,9, 10, 10a-八氢菲-1-羧酸盐)(3)。探讨了化合物23的紫外吸收光谱、荧光发射光谱、溶致变色效应、聚集诱导发光(AIE)特性、热稳定性及电化学性能,并通过理论计算对其结构与性能的关系进行了进一步分析。研究结果表明:与三芳胺基丙烯腈化合物相比,引入脱氢枞酸骨架后,化合物表现出更大的斯托克斯位移、固体状态下更长的红光发射;化合物2表现出AIE特性,而化合物3不具有AIE特性;这两个化合物均具有较好的热稳定性和形态稳定性。脱氢枞酸骨架的引入使得23获得了更高的HOMO、LUMO能级,以及窄的带隙值。

关键词: 脱氢枞酸三芳胺, 丙烯腈, 光物理性能, 聚集诱导发光

Abstract:

Compounds methyl (Z)-6-((4-(5-(2-(3, 5-bis(trifluoromethyl)phenyl)-2-cyanovinyl)thiophen-2-yl) phen-yl)(4-methoxyphenyl)amino)-7-isopropyl-1, 4a-dimethyl-1, 2, 3, 4, 4a, 9, 10, 10a-octahydrophenanthrene-1-carboxylate(2) and dimethyl 6, 6'-(((1-cyanoethene-1, 2-diyl)bis(thiophene-5, 2-diyl))bis(4, 1-phenylene))bis((4-methoxyphen-yl)azanediyl))(E)-bis(7-isopropyl-1, 4a-dimethyl-1, 2, 3, 4, 4a, 9, 10, 10a-octahydrophenanthrene-1-carboxylate)(3) were obtained simply by mixing 5-(dehydroabietic acid triarylamine)-thiophene-2-carbaldehyde and 3, 5-bis(trifluoromethyl)phenylacetonitrile at room temperature and 100 ℃, respectively. The UV-Vis absorption spectra, fluorescence emission spectra, solvatochromism effect, aggregation-induced emission(AIE) characteristics, thermal stability and electrochemical performance of compounds are studied, and the relationship between their structure and performance is further studied through theoretical calculations. Compared with triarylamine-based acrylonitrile compounds, after introducing the dehydroabietic acid skeleton, the compounds show a larger stokes shift and longer red light emission in the solid state. 2 exhibits AIE characteristics, while 3 does not have AIE characteristics. Both of the two compounds have good thermal stability and morphological stability. 2 and 3 have higher highest occupied molecular orbital(HOMO), lowest unoccupied molecular orbital(LUMO) energy levels and narrow band gap, due to the introduction of dehydroabietic acid skeleton.

Key words: dehydroabietic acid triarylamine, acrylonitriles, photophysical properties, aggregation-induced emission(AIE)

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