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Synthesis of a two‐dimensional porphyrin framework connected by 1, 3‐diyne linkages via in situ deprotection of trimethylsilicon at a water/oil interface
Author(s) -
Tan Xianyang,
Li Chan,
Li Ming
Publication year - 2021
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.6120
Subject(s) - monomer , porphyrin , alkyne , polymer , interface (matter) , materials science , polymer chemistry , terminal (telecommunication) , in situ , toluene , chemical engineering , chemistry , photochemistry , organic chemistry , molecule , catalysis , computer science , engineering , telecommunications , gibbs isotherm
Developing two‐dimensional (2D) porphyrin frameworks is a hot topic in the research of 2D materials. Glaser reaction between terminal alkyne monomers at an interface is promising for creating 2D polymers, such as graphdiyne. However, the coupling reaction between terminal alkyne–porphyrin monomers is impossible due to insolubility in low‐polarity solvents. Herein we used a trimethylsilicon (TMS)‐protected precursor as monomer directly and the above problem was solved by in situ deprotection of TMS at a water/toluene interface. The obtained 2D porphyrin framework connected by 1,3‐diyne linkages exhibits nanometer thickness and can be free‐standing under ambient conditions. This method not only reduces the workload of monomer synthesis, but also overcomes the limitation of Glaser reaction for producing 2D polymer films at an interface when the terminal alkyne monomer is insoluble in nonpolar solvents. © 2020 Society of Industrial Chemistry