Synthesis of alkoxy-substituted ortho-phenylene ethynylene oligomers.
[structure: see text] This Letter describes the first published synthesis and characterization of alkoxy-substituted ortho-phenylene ethynylene (o-PE) oligomers. Sonogashira coupling was used to assemble discrete chain lengths, using a key monomer with orthogonal groups. Deprotection or activation allowed stepwise coupling to produce the dimer, trimer, and tetramer, while convergent coupling of appropriately substituted trimers produced the hexamer. The placement of alkoxy side chains renders these oligomers soluble in common organic solvents permitting solution characterization. Absorption and emission spectra of the trimer, tetramer, and hexamer are provided.
Jones
Ticora V
TV
Polymer Science and Engineering, University of Massachusetts, Amherst, Massachusetts 01002, USA.
Blatchly
Richard A
RA
Tew
Gregory N
GN
D000480:Alkynes / Q000138:chemical synthesis*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis*; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry; D013057:Spectrum Analysis
D000480:Alkynes; D004852:Epoxy Compounds; D004987:Ethers; D011108:Polymers; D012997:Solvents; C436384:phenyleneethynylene