Abstract
Palladium-catalyzed polymerization of 6,15-dibromo-2,11-dithia[3.3]metacyclophane 5 and 2,5-dialkoxy-1,4-diethynylbenzenes 6a–b was carried out to give the corresponding polymers 7a–b having dithia[3.3]metacyclophane as a repeating unit. The structures of the polymers were supported by 1H, 13C NMR, and IR spectra. The polymers obtained were soluble in common organic solvents such as tetrahydrofuran (THF), CH2Cl2, CHCl3, and toluene. The polymer 7b showed an extension of π-delocalization via the through-space with π-π stacking according to the UV-vis absorption spectrum in comparison with those of the model compounds 8 and 9. In the fluorescence emission spectrum of 7b in chloroform solution, an intense emission peak was observed at 439 nm (Φ = 0.51) in the visible blue region. The monomer 5, polymers 7a–b, and the model compound 9 adopted the syn conformation of the dithia[3.3]metacyclophane moieties according to the 1H NMR spectra.
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Morisaki, Y., Ishida, T. & Chujo, Y. Synthesis and Optical Properties of Novel Through-Space π-Conjugated Polymers Having a Dithia[3.3]metacyclophane Skeleton in the Main Chain. Polym J 35, 501–506 (2003). https://doi.org/10.1295/polymj.35.501
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DOI: https://doi.org/10.1295/polymj.35.501
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