One-pot synthesis of N-confused porphyrin-dipyrrin conjugates and their optical properties

Nuonuo Zhang; Liu Wen; Xiang Liu; Weifeng Chen; Jiaying Yan

doi:10.1016/j.saa.2019.117661

One-pot synthesis of N-confused porphyrin-dipyrrin conjugates and their optical properties

Spectrochim Acta A Mol Biomol Spectrosc. 2020 Feb 15:227:117661. doi: 10.1016/j.saa.2019.117661. Epub 2019 Oct 17.

Authors

Nuonuo Zhang¹, Liu Wen¹, Xiang Liu¹, Weifeng Chen¹, Jiaying Yan²

Affiliations

¹ College of Materials and Chemical Engineering and Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Hubei, Yichang, 443002, PR China.
² College of Materials and Chemical Engineering and Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Hubei, Yichang, 443002, PR China; State Key Laboratory of Coordination Chemistry, Nanjing University, Jiangsu, Nanjing, 210093, PR China. Electronic address: yanjiaying327@126.com.

PMID: 31734569
DOI: 10.1016/j.saa.2019.117661

Abstract

A conjugated N-confused porphyrin-dipyrrin system NCP-IN-X (X = H, Br, Cl, OMe, COOEt) has been reported via N-Confused tetraphenylporphyrin (NCTPP) as a π-enlarged pyrrole and substituted trimethylindole subunits in 75-82% yields by one pot. All the NCP-INs show red-shifted absorption and emission in the NIR range compared with NCTPP in a series nonpolar and polar solvents. Interesting, relative higher emission in DMF can be observed. The structures of dipyrrin-NCP conjugates are characterized by ¹H-NMR and high resolution mass spectrum (HR-MS). Four frontier molecular orbital and simulated stick absorption spectra are calculated by DFT and TD-DFT calculation which is in good agreement with the experiments.

Keywords: BODIPYs; Dipyrrins; N-confused porphyrin; Near-infrared range; Optical properties.