Fourfold alkoxy-substituted [2.2.2]paracyclophane-1,9,17-trienes-ROMP into PPVs with unusual topologies.
The synthesis of two 4,7,12,15-tetrakisalkoxy-substituted [2.2.2]-paracyclophane-1,9,17-trienes and their polymerization employing ring opening metathesis polymerization (ROMP) using Ru-carbenes (third-generation Grubbs catalyst) is reported. Phenylene ethynylene trimers are reduced via a Grignard reagent, followed by an intramolecular McMurry cyclization to give the cyclophenes. The cyclophenes are polymerized into soluble poly(para-phenylene vinylene)s (PPV), which are analyzed in solution by NMR, UV-vis, and fluorescence spectroscopy. They are spin coated into amorphous, fluorescent thin films, and investigated by optical spectroscopy and cyclic voltammetry.
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120, Heidelberg, Germany.
Dominic
D
Mäker
Uwe H F
UH
Bunz
D000438:Alcohols / Q000737:chemistry*; D055664:Electrochemical Techniques; D004583:Electrons; D004988:Ethers, Cyclic / Q000737:chemistry*; D008027:Light; D058105:Polymerization; D011145:Polyvinyls / Q000138:chemical synthesis / Q000737:chemistry*; D012996:Solutions; D013057:Spectrum Analysis
D000438:Alcohols; D004988:Ethers, Cyclic; D011145:Polyvinyls; D012996:Solutions; C059688:alkoxyl radical; C530822:oligo(p-phenylene vinylene)
PPV; ROMP; conjugated polymers; cyclophanetrienes; metathesis