Polymerization of novel methacrylated anthraquinone dyes

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Abstract

A new series of polymerizable methacrylated anthraquinone dyes has been synthesized by nucleophilic aromatic substitution reactions and subsequent methacrylation. Thereby, green 5,8-bis(4-(2-methacryloxyethyl)phenylamino)-1,4- dihydroxyanthraquinone (2), blue 1,4-bis(4-((2-methacryloxyethyl)oxy) phenylamino)anthraquinone (6) and red 1-((2-methacryloxy-1,1- dimethylethyl)amino)anthraquinone (12), as well as 1-((1,3-dimethacryloxy-2- methylpropan-2-yl)amino)anthraquinone (15) were obtained. By mixing of these brilliant dyes in different ratios and concentrations, a broad color spectrum can be generated. After methacrylation, the monomeric dyes can be covalently emplaced into several copolymers. Due to two polymerizable functionalities, they can act as cross-linking agents. Thus, diffusion out of the polymer can be avoided, which increases the physiological compatibility and makes the dyes promising compounds for medical applications, such as iris implants. © 2013 Dollendorf et al; licensee Beilstein-Institut.

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Dollendorf, C., Kreth, S. K., Choi, S. W., & Ritter, H. (2013). Polymerization of novel methacrylated anthraquinone dyes. Beilstein Journal of Organic Chemistry, 9, 453–459. https://doi.org/10.3762/bjoc.9.48

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