Water-soluble DNA cross-linking phenol and biphenol derivatives 3 and 6 have been synthesized by a Mannich reaction. Both of them can cross-link DNA by photoactivation using visible light (wavelength > 400 nm). Compound 6 can cross-link DNA at pH 5.0 and 7.7, whereas no cross-link was observed at pH 10.0. Density functional theory (DFT) calculation indicated that 6 displays a twist structure. Therefore, it could bind to DNA naturally and has potent property to cross-link DNA after photoactivation.

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Herein, we report the reaction of quinoline with diphenylphosphine oxide in the presence of visible light without catalyst. The reaction completes in 24 h under the mild conditions and the substrates are well tolerant. This method provides a straightforward and environmentally friendly access to diphosphorous quinoline compounds. Similarly, this method can also aid in the phosphate functionalization of some heterocyclic compounds.