The polycycloaddition of azomethine ylides to dipolarophiles is described for the first time. Use of (cis,cis)-bis-aziridines as a source of azomethine ylides allows selective polyaddition to be realized, which leads to oligomers exclusively with trans-substituted pyrrolidine rings and modest molecular weights (ca. 5–10 kDa). The fluorescent, electrochemical, electrochromic, and non-linear optical properties of the main-chain free-base porphyrin oligomer, synthesized by the developed procedure, are studied. An enhancement of the optical power limiting effect in a porphyrin oligomer solution is registered against that of the monomer.
Konev, A. S., Lukyanov, D. A., Vlasov, P. S., Levin, O. V., Virtsev, A. A., Kislyakov, I. M., & Khlebnikov, A. F. (2014). The Implication of 1,3-Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main-Chain Porphyrin Oligomers. Macromolecular Chemistry and Physics, 215(6), 516-529. https://doi.org/10.1002/macp.201300679