Dehydroabietic Acid Triarylamine-based Acrylonitrile Compounds: Synthesis and Photophysical Properties
2022, 42 (3):
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.
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