Synthesis, one/two-photon optical and electrochemical properties and the photopolymerization-sensitizing effect of anthracene-based dyes: influence of the donor groups

Abstract

Four anthracene-based dyes (ANDs) with different donor groups, namely 9,10-bis(phenylethynyl)anthracene (A1), 9,10-bis((9-dodecyl-9H-carbazol-3-yl)ethynyl) anthracene (A2), 9,10-bis((10-dodecyl-10H-phenothiazin-3-yl)ethynyl)anthracene (A3), and 4,4′-(anthracene-9,10-diylbis(ethyne-2,1-diyl))bis(N,N-diphenylaniline) (A4) were synthesized and characterized. The ANDs showed considerable absorption in blue/green regions and strong fluorescence emission in the green to red region. Besides, the ANDs possess large two-photon absorption cross-sections at 780–880 nm. Electrochemical studies revealed that these electron donors possess different donating abilities which in turn influence the redox potential and excited intramolecular charge transfer intensity of the ANDs. The conjugation degree among the donor groups and anthracene also has a significant impact on the redox potential of the ANDs. Moreover, compounds A1, A2, and A3 are able to couple with iodonium salt to initiate radical photopolymerization under blue and green LED irradiation. In summary, the structure–property relationships were investigated in detail in this work, which may provide useful guidance for further research.