1032358-08-9Relevant articles and documents
Syntheses of sterically hindered zwitterionic pyridinium phenolates as model compounds in nonlinear optics
Diemer, Vincent,Chaumeil, Helene,Defoin, Albert,Fort, Alain,Boeglin, Alex,Carre, Christiane
body text, p. 1767 - 1776 (2009/04/11)
Pyridinium phenolates possess a dissymmetric delocalised π-electron system providing a huge quadratic nonlinearity. They are a promising class of molecules for applications in photoelectronics and photonics. Semiempirical calculations indicate that the interplanar angle between the two aromatic rings leads to enhancement in the NLO properties of these compounds. The confirmation of this feature may be provided by the study of a new series of sterically hindered pyridinium phenolates 2a-e bearing two tert-butyl substituents at the ortho position(s) of the phenolate functionality. Such bulky groups would enhance the solubility of zwitterions in organic solvents and would limit the formation of aggregates. Their efficient preparations by using Suzuki cross-coupling reactions involving 3,5-dialkylated 4-bromopyridine N-oxides are described herein. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.