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Synthesis and characterization of push-pull molecules bearing tetrafluorobenzene central acceptor modified with two peripheral hexyloxy and dihexylamino donors
Authors: Ramaiyan Manikannan | Kulhánek Jiří | Bureš Filip
Year: 2014
Type of publication: článek v odborném periodiku
Name of source: Scientific Papers of the University of Pardubice, Series A, Faculty of Chemical Technology
Publisher name: Univerzita Pardubice
Place: Pardubice
Page from-to: 249-261
Titles:
Language Name Abstract Keywords
cze Syntéza a charakterizace push-pull molekul obsahujících jako centrální donor tetrafluorbenzen, který nese akceptorní substituenty hexyloxy a dihexylamino skupinu S pomocí Suzuki-Miyaura a Sonogashira reakce byly připraveny nové push-pull molekuly. Syntézy vycházely z 1,4-dijodtetrafluorbenzenu nebo 1,4-bis(5-bromthiofen-2-yl)tetrafluorbenzenu, který byl substituován dvěma perifenrími donorními substituenty, N,N-dihexylamino skupinou a O-hexyloxy skupinou. Struktura, délka a planarita skeletu molekuly spojující donorní a akceptorní jednotku byla modifikována s využitím 1,4-fenylenové, 2,5-thienylenové nebo acetylenové jednotky. thiofen;tetrafluorbenzen;push-pull molekula;scorr-coupling reakce;NLO vlastnosti
eng Synthesis and characterization of push-pull molecules bearing tetrafluorobenzene central acceptor modified with two peripheral hexyloxy and dihexylamino donors Starting from 1,4-diiodotetrafluorobenzene or 1,4-bis(5-bromothiophene-2-yl)tetrafluorobenzene, four new push-pull molecules were synthesized via twofold cross-coupling reactions. Suzuki-Miyaura and Sonogashira reactions were employed to gain access to target molecules. The central tetrafluorobenzene acceptor unit was modified by two peripheral N,N-dihexylamino and O-hexyloxy groups with different donating ability to generate quadrupolar D-π-A-π-D system with tailored intramolecular charge-transfer. The length, planarity and composition of the π-linker between the acceptor and donors was modified by combination of 1,4-phenylene, 2,5-thienylene and acetylenic subunits in order to finely tune the linear as well as nonlinear optical properties. thiophene;tetrafluorobenzene;push-pull molecule;cross-coupling reaction;charge-transfer;NLO properties

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