Syntheses and Structures of Functionalized [9]Cycloparaphenylenes as Carbon Nanohoops Bearing Carbomethoxy and N-Phenylphthalimido Groups.
Functionalized [9]cycloparaphenylenes ([9]CPPs) bearing nine aromatic units in the macrocyclic structures were synthesized. The macrocyclic structures were substituted with carbomethoxy or N-phenylphthalimido groups. The Diels-Alder reaction of (E,E)-1,4-bis(4-bromophenyl)-1,3-butadiene or a related diene with dimethyl acetylenedicarboxylate followed by the nickel-mediated homocoupling reactions and oxidative aromatization produced the functionalized [9]CPPs. Treatment of a resultant [9]CPP with aniline or 1,4-diaminobenzene gave the corresponding N-phenylphthalimides. The X-ray structure of a [9]CPP bearing six carbomethoxy groups was obtained.
C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
Shuangjiang
S
Li
C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
Changfeng
C
Huang
C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
Haresh
H
Thakellapalli
C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
Behzad
B
Farajidizaji
C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
Brian V
BV
Popp
C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
Jeffrey L
JL
Petersen
C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
Kung K
KK
Wang