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The Implication of 1,3‐Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main‐Chain Porphyrin Oligomers
Author(s) -
Konev Alexander S.,
Lukyanov Daniil A.,
Vlasov Petr S.,
Levin Oleg V.,
Virtsev Alexander A.,
Kislyakov Ivan M.,
Khlebnikov Alexander F.
Publication year - 2014
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201300679
Subject(s) - oligomer , porphyrin , chemistry , monomer , polymer chemistry , electrochromism , cycloaddition , pyrrolidine , photochemistry , electrochemistry , organic chemistry , polymer , electrode , catalysis
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.