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Syntheses And Structures Of Functionalized Cycloparaphenylenes And Fused Cycloparaphenylene Precursors., Changfeng Huang

Graduate Theses, Dissertations, and Problem Reports

A synthetic pathw ay o f preparing functionalized [9]cycloparaphenylene ([9]CPP) bearing three evenly spaced 5,8-dim ethyoxynaphth-l,4-diyl units and tw o m acrocyclic [6]CPP precursors has been developed. The key steps included the D iels-A ld er reaction betw een (E,E)-1,4-bis(4-brom ophenyl)- 1,3-butadiene and 1,4-benzoquinone followed by m ethylation to produce an L-shaped building block w ith tw o 4-brom ophenyl groups cis to each other exclusively, the nickel-m ediated hom ocoupling reactions to construct the m acrocyclic dim ers and trim ers, and m ild, efficient oxidative arom atization by 2,3- dichloro-5,6-dicyano- 1,4-benzoquinone (D D Q ) to furnish the …