TY - JOUR
T1 - Synthesis and properties of novel stilbazolium analogues as second-order nonlinear optical chromophores
AU - Tsuji, Kyoko
AU - Nishimura, Naoyuki
AU - Duan, Xuan Ming
AU - Okada, Shuji
AU - Oikawa, Hidetoshi
AU - Matsuda, Hiro
AU - Nakanishi, Hachiro
PY - 2005/1
Y1 - 2005/1
N2 - This study synthesized a series of methoxystilbazolium analogues with π-conjugation extended by attaching a fused aromatic ring, i.e., 6-styrylisoquinolinium and 4-[2-(2-naphthyl)ethenyl]pyridinium derivatives with methoxy substituents. We evaluated their transition energies (EegS) and second-order hyperpolarizabilities (βs) experimentally using their absorption spectra and a hyper-Rayleigh scattering measurement, respectively. Subsequently, we calculated βs using the MOPAC PM3 method. These values were compared with those of 4-[4-(4-methoxyphenyl)-1,3-butadienyl]pyridinium derivative, which is a stilbazolium analogue with π-conjugation that is simply extended by an increase of the double-bond number between two aromatic rings. This study clarified that the fused-ring systems possess large βs, irrespective of their relatively short absorption wavelengths, compared to the double-bond elongation system.
AB - This study synthesized a series of methoxystilbazolium analogues with π-conjugation extended by attaching a fused aromatic ring, i.e., 6-styrylisoquinolinium and 4-[2-(2-naphthyl)ethenyl]pyridinium derivatives with methoxy substituents. We evaluated their transition energies (EegS) and second-order hyperpolarizabilities (βs) experimentally using their absorption spectra and a hyper-Rayleigh scattering measurement, respectively. Subsequently, we calculated βs using the MOPAC PM3 method. These values were compared with those of 4-[4-(4-methoxyphenyl)-1,3-butadienyl]pyridinium derivative, which is a stilbazolium analogue with π-conjugation that is simply extended by an increase of the double-bond number between two aromatic rings. This study clarified that the fused-ring systems possess large βs, irrespective of their relatively short absorption wavelengths, compared to the double-bond elongation system.
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U2 - 10.1246/bcsj.78.180
DO - 10.1246/bcsj.78.180
M3 - Article
AN - SCOPUS:13444279937
VL - 78
SP - 180
EP - 186
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
IS - 1
ER -