A Porphyrin-Based Organic Network Comprising Sustainable Carbon Dots for Photopolymerization

Xiongfei Luo; Jianyong Wan; Nicolai Meckbach; Veronika Strehmel; Shujun Li; Zhijun Chen; Bernd Strehmel

doi:10.1002/anie.202208180

A Porphyrin-Based Organic Network Comprising Sustainable Carbon Dots for Photopolymerization

Angew Chem Int Ed Engl. 2022 Oct 4;61(40):e202208180. doi: 10.1002/anie.202208180. Epub 2022 Sep 1.

Authors

Xiongfei Luo^{1

2}, Jianyong Wan¹, Nicolai Meckbach², Veronika Strehmel², Shujun Li¹, Zhijun Chen¹, Bernd Strehmel²

Affiliations

¹ Northeast Forestry University, Key Laboratory of Bio-based Material Science and Technology of Ministry of Education, Hexing Road 26, 150040, Harbin, China.
² Department of Chemistry, Institute for Coatings and Surface Chemistry, Niederrhein University of Applied Sciences, Adlerstr. 1, 47798, Krefeld, Germany.

Abstract

Sustainable carbon dots (CDs) based on furfuraldehyde (F-CD) resulted in a photosensitive material after pursuing the Alder-Longo reaction. The porphyrin moiety formed connects the F-CDs in a covalent organic network. This heterogeneous material (P-CD) was characterized by XPS indicating incorporation of the respective C, N and O moieties. Time resolved fluorescence including global analysis showed contribution of three linked components to the overall dynamics of the excited state. Electrochemical and photonic properties of this heterogeneous material facilitated photopolymerization in a photo-ATRP setup where either CuBr₂ /TPMA, FeBr₃ /Br^- or a metal free reaction setup activated controlled polymerization. Chain extension experiments worked in all three cases showing end group fidelity for activation of controlled block copolymerization using MMA and styrene as monomers. Traditional radical polymerization using a diaryl iodonium salt as co-initiator failed.

Keywords: Carbon Dots; Photo-ATRP; Porphyrins; Sensitization; Visible-Light LEDs.

Abstract

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