Synthesis of nonlinear optical chromophores containing electron-excessive and -deficient heterocyclic bridges. The auxiliary donor–acceptor effects

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Ching-fong Shu and Yuh-kai Wang


Abstract

Push-pull substituted nonlinear optical chromophores with thiazole and thiophene rings and interposed ethylene units as π-conjugated bridges were synthesized. The effects of the nature and location of the heterocycles on the energy of the charge transfer transition for the chromophores are discussed.


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  11. 1H NMR spectra were recorded using CD2Cl2 as solvent and TMS as internal standard. Chemical shifts are in ppm, coupling constants are in Hz. 5c: δ 1.21 (t, 6H, J 7.1), 3.42 (q, 4H, J 7.1), 6.01 (d, 1H, J 4.6), 6.46 (d, 1H, J 14.3), 7.24 (d, 1H, J 4.6), 7.85 (d, 1H, J 14.3), 8.34 (s, 1H). 5d: δ 1.17 (t, 6H, J 7.1), 3.33 (q, 4H, J 7.1), 5.82 (d, 1H, J 4.3), 6.48 (d, 1H, J 14.9), 7.05 (d, 1H, J 4.3), 7.69 (d, 1H, J 14.9), 7.71 (s, 1H), 7.99 (s, 1H). 7c: δ 1.18 (t, 6H, J 7.0), 3.48 (q, 4H, J 7.0), 6.47 (d, 1H, J 15.5), 7.05 (d, 1H, J 4.4), 7.32 (d, 1H, J 15.5), 7.35 (s, 1H), 7.83 (d, 1H, J 4.4). 7d: δ 1.17 (t, 6H, J 7.1), 3.45 (q, 4H, J 7.1), 6.48 (d, 1H, J 15.5), 6.96 (d, 1H, J 4.2), 7.20 (d, 1H, J 15.5), 7.22 (s, 1H), 7.49 (d, 1H, J 4.2), 7.65 (s, 1H). HRMS (m/z)5c: Obs. 365.0745, calc. 365.0768; 5d: obs. 340.0810, calc. 340.0816; 7c: obs. 365.0751, calc. 365.0768; 7d: obs. 340.0814, calc. 340.0816.
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