Synthesis and characterization of tetrathiafulvalene-substituted di- and tetraethynylethenes with p-nitrophenyl acceptors.
Novel di- and tetraethynylethene (DEE and TEE) compounds functionalized with tetrathiafulvalene (TTF) donor groups and p-nitrophenyl acceptor groups were synthesized by palladium-catalyzed cross-coupling reactions under various conditions. The molecules are strong chromophores and were investigated for their optical properties. Placement of two TTFs and two p-nitrophenyls about a central TEE core provides a molecule with a high third-order optical nonlinearity. The molecules experience reversible oxidations of the TTF units, and the optical properties of the oxidized species were elucidated by spectroelectrochemistry. The degree of quinoid character of the p-nitrophenyl in the molecules was determined by X-ray crystallography.
Andersson
Asbjørn S
AS
Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark.
Kerndrup
Lasse
L
Madsen
Anders Ø
AØ
Kilså
Kristine
K
Nielsen
Mogens Brøndsted
MB
D002384:Catalysis; D018360:Crystallography, X-Ray; D053281:Enediynes / Q000138:chemical synthesis* / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009596:Nitrophenols / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D053281:Enediynes; D006571:Heterocyclic Compounds; D009596:Nitrophenols; C520450:tetraethynylethene; D010165:Palladium; C063887:tetrathiafulvalene