Synthesis and Properties of Novel Stilbazolium Analogues as Second-Order Nonlinear Optical Chromophores

Kyoko Tsuji, Naoyuki Nishimura, Xuan-Ming Duan, Shuji Okada, Hidetoshi Oikawa, Hiro Matsuda, Hachiro Nakanishi
2005 Bulletin of the Chemical Society of Japan  
This study synthesized a series of methoxystilbazolium analogues with -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 (E eg s) and second-order hyperpolarizabilities (s) experimentally using their absorption spectra and a hyper-Rayleigh scattering measurement, respectively. Subsequently, we calculated s using the MOPAC PM3 method. These
more » ... es were compared with those of 4-[4-(4-methoxyphenyl)-1,3-butadienyl]pyridinium derivative, which is a stilbazolium analogue with -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 s, irrespective of their relatively short absorption wavelengths, compared to the double-bond elongation system.
doi:10.1246/bcsj.78.180 fatcat:3twp2b4ut5ecli3k2y54bcvdry