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New noncentrosymmetric compounds having both electron-accepting and electron-donating substituents on a conjugated, aromatic heterocyclic structure were synthesized and their spectroscopic, thermal, and solubility properties were determined. D.C. electric field-induced second harmonic generation (EFISH) experiments were performed to provide values of the second-order nonlinear optical susceptibility/dipole moment product βμ. Long alkyl substituents were required in heterocycle-containing compounds for sufficient solubility to conduct EFISH analysis. 2,4-Dinitro-substitution on these imine-linked materials gave the highest βμ in the series.
This paper reports the synthesis method for polymerizaing poly(2,6-benzothiazole) (ABPBT) and poly(2,5-benzoxazole) (ABPBO), and their dilute solution properties using low angle light scattering and viscometry. Our data indicate that the Mark-Houwink-Sakurada exponents for these extended-chain polymers are near unity, suggesting a semi-rigid conformation in dilute solutions. The solution properties agree well with the Yamakawa-Fujii worm-like chain model when persistence lengths of 130 Å and 90 Å are assumed for ABPBT and ABPBO, respectively. These values of persistence length are also in good agreement with those predicted by Flory's virtual bond model using information on the molecular geometries taken from x-ray crystallographic data on oriented fibers of ABPBT and ABPBO.
The synthesis of three types of functionalized benzazole structures is described. A centrosymmetric dihydroxy-benzobisthiazole has been synthesized for incorporation in flexible polymers having rigid, conjugated, third order nlo active units in the main chain. Benzazole structures terminated with an N,N-dimethylamino group and a carboxyl group have been synthesized for use as second order nlo pendants with flexible polymers. Benzazole structures terminated with an N,N-dimethylamino group and an amino group have been synthesized as precursors to second order nlo guest molecules.
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