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Chemistry and Industry of Forest Products ›› 2022, Vol. 42 ›› Issue (3): 10-18.doi: 10.3969/j.issn.0253-2417.2022.03.002

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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

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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