Title: The syntheses, structures and nonlinear optical and related properties of salts with julolidinyl electron donor groups
Authors: Coe, Benjamin J ×
Foxon, Simon P
Harper, Elizabeth C
Harris, James A
Helliwell, Madeleine
Raftery, James
Asselberghs, Inge
Clays, Koen
Franz, Edith
Brunschwig, Bruce S
Fitch, Anthony G #
Issue Date: Aug-2009
Publisher: Applied Science Publishers
Series Title: Dyes and Pigments vol:82 issue:2 pages:171-186
Abstract: Twelve. dipolar cations with 2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl (julolidinyl, Jd) electron donor groups and N-methyl/arylpyridinium, N-methylquinolinium or N-methylbenzothiazolium acceptor groups were synthesised. The chromophores were characterised as their PF6- salts using various techniques including electronic absorption spectroscopy and cyclic voltammetry; single crystal X-ray structures were determined for a large number of salts, all of which form nonpolar materials. A broad correlation between the electron acceptor strength and the degree of bond length alternation is evident. A key focus of this work is detailed comparisons of the Jd-containing chromophores with their previously studied 4-(dimethylamino)phenyl (Dap) analogues. Molecular, quadratic, nonlinear optical responses were determined using femtosecond hyper-Rayleigh scattering at both 1300 and 800 nm, as well as using Stark (electroabsorption) spectroscopic studies of intense, visible pi -> pi* intramolecular charge-transfer bands. Substantial red shifts in the latter transitions are observed on replacing Dap with Jd which indicate that the latter acts as a more effective pi-electron donor. With few exceptions, both hyper-Rayleigh scattering and Stark data generally show that using Jd instead of Dap increases the static first hyperpolarizability beta(0), in accord with expectations based on the two-state model. beta(0) values as high as 6 times larger than that of the chromophore in the technologically important material E-4'-(dimethylamino)-N-methyl-4-stilbazolium tosylate are observed. (C) 2009 Elsevier Ltd. All rights reserved.
ISSN: 0143-7208
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Imaging and Photonics
× corresponding author
# (joint) last author

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