The Implication of 1,3-Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main-Chain Porphyrin Oligomers

A.S. Konev, D.A. Lukyanov, P.S. Vlasov, O.V. Levin, A.A. Virtsev, I.M. Kislyakov, A.F. Khlebnikov

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3 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)516-529
JournalMacromolecular Chemistry and Physics
Volume215
Issue number6
DOIs
Publication statusPublished - 2014

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