ORGN 656 |
| The 1,4-bisarylethynyl-2,5-distyrylbenzenes, cruciforms, are synthesized by an Arbuzow reaction of 2,5-bisbromomethyl-1,4-diiodobenzene with triethylphosphite followed by a Horner reaction to attach the styryl units. The synthesis is finished by a Heck-Cassar-Sonogashira-Hagihara coupling to an arylalkyne to give the desired cruciforms. If the two branches of the cruciforms are donor and acceptor substituted, respectively, fluorophores with spatially separated frontier molecular orbitals result. The two chemically different branches carrying HOMO and LUMO respectively, can be addressed by metal cations or by proton acid to give large responses, i.e. bathochromic or hypsochromic shifts, in absorption and particularly in emission. The cruciforms are primitive, yet functionally operative sensory materials, which upon addition of suitable ionophores should give rise to metal ion sensors. |
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Modern Acetylene Chemistry
1:20 PM-4:55 PM, Wednesday, 13 September 2006 Moscone Center -- Room 134, Oral
Division of Organic Chemistry |