Functionalized carbon nanohoops: synthesis and structure of a [9]cycloparaphenylene bearing three 5,8-dimethoxynaphth-1,4-diyl units.
A functionalized [9]cycloparaphenylene ([9]CPP) bearing three evenly spaced 5,8-dimethoxynaphth-1,4-diyl units and two macrocyclic [6]CPP precursors have been synthesized. The Diels-Alder reaction between (E,E)-1,4-bis(4-bromophenyl)-1,3-butadiene and 1,4-benzoquinone followed by methylation produces cis-5,8-bis(4-bromophenyl)-5,8-dihydro-1,4-dimethoxynaphthalene as the key intermediate for the construction of the hooplike structures. The nickel-mediated homocoupling reactions followed by aromatization led to the functionalized [9]CPP.
C. Eugene Bennett Department of Chemistry, West Virginia University , Morgantown, West Virginia 26506-6045, United States.
Changfeng
C
Huang
Yiwei
Y
Huang
Novruz G
NG
Akhmedov
Brian V
BV
Popp
Jeffrey L
JL
Petersen
Kung K
KK
Wang