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

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.

Synthesis of New Porphyrin–Fullerene Dyads Capable of Forming Charge‐Separated States on a Microsecond Lifetime Scale

“…-1250 www.chemeurj.org 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim onset voltage of the second peak and attained maximum intensity at the peak voltage of the second peak seen in the CV (Figures 11 and 12). According to our previous findings, [29] the band at 665 nm is typical of a reduced porphyrin moiety. Hence, the first peak corresponds to reduction of the fullerene core, and the second peak corresponds to reduction of the porphyrin moiety.…”