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Two series of novel push-pull heterocyclic azo dyes have been synthesized and characterized. The two series of compounds were based on different combinations of pi-conjugated bridges (bithiophene and thienylpyrrole) which also act simultaneously as donor groups, together with diazo(benzo) thiazolyl as acceptor moieties. Their thermal stability and electrochemical behavior were characterized, while hyper-Rayleigh scattering (HRS) was employed to evaluate their second-order nonlinear optical properties. The results of these studies have been critically analyzed together with several thienylpyrrole azo dyes reported earlier from our laboratories in which the thienylpyrrole system was used as the donor group functionalized with aryl and (benzo)thiazolyldiazene as acceptor moiety. The measured molecular first hyperpolarizabilities and the observed linear optical and redox behavior showed strong variations in function of the heterocyclic spacers used (bithiophene or thienylpyrrole) and were also sensitive to the acceptor strength of the diazenehetero(aryl) moiety.Thanks are due to the <IT>Fundacao para a Ciencia e Tecnologia</IT> (Portugal) and FEDER for financial support through the Centro de Quimica and Centro de Fisica-Universidade do Minho, Project PTDC/QUI/66251/2006 (FCOMP-01-0124-FEDER-007429), Project PTDC/CTM/105597/2008 with funding from COMPETE/FEDER and a research grant to M. C. R. Castro (UMINHO/BI/142/2009). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT.info:eu-repo/semantics/publishedVersio

Synthesis and evaluation of NLO properties of π-conjugated donor-acceptor systems bearing pyrrole and thiophene heterocycles