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Synthesis, Characterisation and Nonlinear Optical Properties of Two‐Dimensional Octupolar Systems Based on Phthalocyanine Compounds
Author(s) -
Quintiliani Maurizio,
GarcíaFrutos Eva M.,
Gouloumis Andreas,
Vázquez Purificación,
LedouxRak Isabelle,
Zyss Joseph,
Claessens Christian G.,
Torres Tomás
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500271
Subject(s) - chemistry , sonogashira coupling , benzene , tris , knoevenagel condensation , benzene derivatives , condensation , triazine , nonlinear optical , palladium , computational chemistry , combinatorial chemistry , polymer chemistry , organic chemistry , nonlinear system , chemical synthesis , thermodynamics , biochemistry , physics , quantum mechanics , in vitro , catalysis
Abstract Four phthalocyanine‐based compounds with pseudo D 3 h symmetry have been synthesised and fully characterised. Palladium cross‐coupling methodologies were employed in order to synthesise 1,3,5‐tris[(phthalocyaninyl)ethenyl]benzene (Heck) and 1,3,5‐tris[(phthalocyaninyl)ethynyl]benzene (Sonogashira) derivatives. Knoevenagel condensation conditions were then applied to the synthesis of 1,3,5‐tris[cyano(phthalocyaninyl)ethenyl]benzene and 2,4,6‐tris[(phthalocyaninyl)ethenyl]‐1,3,5‐triazine. Preliminary second‐order nonlinear optical studies, by hyper‐Rayleigh scattering measurements, revealed that the compounds containing ethenyl linkers induce a strong octupolar effect while the ethynyl‐containing compound does not show any octupolar enhancement. The introduction of a triazine central core does not modify significantly the nonlinear optical behaviour of the compound. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)