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 produce...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 16; no. 10; pp. 2672 - 2675
Main Authors Huang, Changfeng, Huang, Yiwei, Akhmedov, Novruz G, Popp, Brian V, Petersen, Jeffrey L, Wang, Kung K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.05.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENT
TEMPERATURE
COUPLING REACTIONS
CRYSTAL-STRUCTURE
SELECTIVE SYNTHESIS
NANOTUBE GROWTH
CHIRALITY
NANORINGS
BOTTOM-UP SYNTHESIS
DEPENDENCE
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500904x