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[2.2.2]Paracyclophane-TrienesAttractive Monomers for ROMP

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journal contribution
posted on 20.05.2014, 00:00 by Dominic Mäker, Christopher Maier, Kerstin Brödner, Uwe H. F. Bunz
Three derivatives of 4,7-substituted [2.2.2]­paracyclophane-trienes were synthesized and used in ring-opening metathesis polymerization (ROMP), resulting in well-soluble poly­(para-phenylenevinylene)­s (PPV). The paracyclophane-trienes were prepared using an iterative buildup of a phenylene–ethynylene backbone, followed by a cis selective Grignard reduction and an intramolecular McMurry reaction. The monomers were applied in ROMP to result in well-soluble PPV derivatives with an unusual substituent pattern. The PPVs were spin-coated into amorphous, highly fluorescent films. To the best of our knowledge, we are the first to synthesize 4,7-substituted [2.2.2]­paracyclophane-trienes and use them as ROMP monomers.