Structure-Property Relationships and Nonlinear Optical Effects in Donor-Substituted Dicyanopyrazine-Derived Push-Pull Chromophores with Enlarged and Varied π-Linkers

Autor: Jiří Kulhánek, Tomáš Mikysek, I.V. Kityk, Hana Čermáková, Filip Bureš, Aleš Růžička, Wojciech Kuznik, Miroslav Ludwig
Rok vydání: 2011
Předmět:
Zdroj: European Journal of Organic Chemistry. 2012:529-538
ISSN: 1434-193X
DOI: 10.1002/ejoc.201101226
Popis: Thirteen new, stable, push–pull systems featuring dimethylamino and pyrazine-2,3-dicarbonitrile moieties as the donor and acceptor, respectively, and systematically extended and varied π-linkers were prepared and investigated. Evaluation of the measured UV/Vis spectra, electrochemical data (cyclic voltammetry, rotating disc voltammetry, and polarography), X-ray data, and experimentally determined and calculated hyperpolarizability values enabled structure–property studies; these revealed some important structural features that affected the efficiency of intramolecular charge-transfer and nonlinear optical properties in this class ofheterocyclic push–pull chromophores. The charge-transfer transition was most significantly affected by structuralfeatures such as π-linker length, chromophore planarity, and the number of 1,4-phenylene/ethynylene subunits in the π-linker.
Databáze: OpenAIRE