221292-39-3Relevant articles and documents
Importance of the Anchor Group Position (Para versus Meta) in Tetraphenylmethane Tripods: Synthesis and Self-Assembly Features
Lindner, Marcin,Valá?ek, Michal,Homberg, Jan,Edelmann, Kevin,Gerhard, Lukas,Wulfhekel, Wulf,Fuhr, Olaf,W?chter, Tobias,Zharnikov, Michael,Kolivo?ka, Viliam,Pospí?il, Lubomír,Mészáros, Gábor,Hromadová, Magdaléna,Mayor, Marcel
, p. 13218 - 13235 (2016)
The efficient synthesis of tripodal platforms based on tetraphenylmethane with three acetyl-protected thiol groups in either meta or para positions relative to the central sp3carbon for deposition on Au (111) surfaces is reported. These platfor
4,4″-disubstituted terpyridines and their homoleptic FeII complexes
Harzmann, Gero D.,Neuburger, Markus,Mayor, Marcel
, p. 3334 - 3347 (2013/07/26)
A novel synthetic route to 4,4″-disubstituted-2,2′:6′, 2″-terpyridine ligands by Suzuki-Miyaura cross-coupling was elaborated by synthesizing compounds 4a-5c. The considerable stability of 4-substituted lithium triisopropyl 2-pyridylborates 2a-c, which are less prone to protodeboronation than similarly functionalized neutral boronic acid derivatives, enabled this synthetic route. The terpyridine core structure was further functionalized by exposing 4,4″-dichloroterpyridine (4b) to Suzuki coupling conditions to yield 4,4″-diarylterpyridines 5a-c. Homoleptic FeII complexes 8a-f of the reported terpyridine ligands were formed quantitatively, which demonstrates the lack of steric repulsion of substituents at the 4- and 4″-positions during complexation. The solid-state structures of particular ligands and FeII complexes were analyzed by single-crystal X-ray crystallography. UV/Vis absorption data for the Fe II complexes are also provided to complement the results reported here. A novel synthetic route to terpyridine ligands is reported. Pyridine building blocks are interlinked by Suzuki-Miyaura cross-coupling reactions. The potential of the method is demonstrated by assembling the 4,4″- disubstituted terpyridine ligands shown, which are subsequently converted into their homoleptic FeII complexes. Copyright
Oligoaryl cruciform structures as model compounds for coordination-induced single-molecule switches
Grunder, Sergio,Huber, Roman,Wu, Songmei,Schoenenberger, Christian,Calame, Michel,Mayor, Marcel
scheme or table, p. 833 - 845 (2010/04/05)
The synthesis of two new cruciform structures 3 and 4 comprising an oligo(phenylene-vinylene) (OPV) and a perpendicular oligoaryl bar - namely an oligophenylene (OP) (3) and a naphthyl-phenyl-naphthyl system (4) - is reported. The OPV rod consists of two terminal pyridine units, whereas the oligoaryl rod bears two terminal acetylsulfanyl groups as protected anchor groups. The OPV bar was assembled via a Homer-Wadsworth-Emmons reaction, which directly led to the desired E,E isomers. The perpendicular oligoaryl bars were assembled with a Suzuki reaction using the corresponding boronic acids, which were already fitted with an ethyl-trimethylsilane (ethyl-TMS) sulfanyl group. In a last step, the ethyl-TMS-protected sulfur atoms were transpro-tected to the thioacetyl units. The cruciform structures 3 and 4 are model compounds to investigate a coordinationinduced single-molecule switch exploiting the potentialdependant different bonding strengths of the anchor groups to gold. Metal-molecule-metal junctions were formed using a mechanically controllable break junction (MCBJ) setup. Current traces of molecular junctions were statistically analyzed. Further investigations of model compounds consisting only of the single bar confirm that individual molecules carrying the required function for the switching experiments were trapped between two electrodes and were mainly immobilized via thiol-gold anchor bonds.
