title: Synthesis of Partially Hydrogenated Cycloparaphenylenes with Bent and Fused Structures Bearing Armchair Carbon Nanotube-like Connections.
abstract: The Diels-Alder reactions between 2 equiv of (E,E)-1,4-bis(4-bromophenyl)-1,3-butadiene and 1,4-benzoquinone led to the formation of a key intermediate with all four 4-bromophenyl substituents cis to one another. The subsequent nickel-mediated homocoupling reactions then produced partially hydrogenated cycloparaphenylenes, including a molecule bearing two units of tetrahydro[6]cycloparaphenylene (4H[6]CPP) fused together through two 1,4-dimethoxybenzene units in an armchair (6,6)carbon nanotube-like connection. Similarly, two 6H[9]CPPs were connected through three 1,4-dimethoxybenzene units in an armchair (9,9)carbon nanotube-like arrangement. A bent 8H[12]CPP and a bent 12H[18]CPP, which were fused intramolecularly with two and three 1,4-dimethoxybenzene units, respectively, to create the bent structures, were likewise synthesized. A molecule containing a bent 8H[12]CPP fused to a 4H[6]CPP was likewise constructed. The structures of these partially hydrogenated CPPs were established by X-ray structure analysis, NMR spectroscopy, and additional independent synthetic pathways.
authors.affiliation: C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
authors.forename: Changfeng
authors.initials: C
authors.lastname: Huang
authors.affiliation: C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
authors.forename: Shuangjiang
authors.initials: S
authors.lastname: Li
authors.affiliation: C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
authors.forename: Haresh
authors.initials: H
authors.lastname: Thakellapalli
authors.affiliation: C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
authors.forename: Behzad
authors.initials: B
authors.lastname: Farajidizaji
authors.affiliation: C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
authors.forename: Yiwei
authors.initials: Y
authors.lastname: Huang
authors.affiliation: C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
authors.forename: Novruz G
authors.initials: NG
authors.lastname: Akhmedov
authors.affiliation: C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
authors.forename: Brian V
authors.identifier: 0000-0001-6367-1168
authors.initials: BV
authors.lastname: Popp
authors.affiliation: C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
authors.forename: Jeffrey L
authors.initials: JL
authors.lastname: Petersen
authors.affiliation: C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
authors.forename: Kung K
authors.identifier: 0000-0001-7039-2984
authors.initials: KK
authors.lastname: Wang