An Aza-Diels–Alder Approach to Crowded Benzoquinolines

Graphene nanoribbons (GNRs) are promising candidate materials for the next generation of nanoscale electronics. Described herein is the synthesis of 2,4,6-substituted benzoquinolines, which constitute building blocks for nitrogen-doped GNRs. The presented facile and modular aza-Diels–Alder chemistry...

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Published inOrganic letters Vol. 18; no. 2; pp. 156 - 159
Main Authors Mazaheripour, Amir, Dibble, David J, Umerani, Mehran J, Park, Young S, Lopez, Robert, Laidlaw, Dylan, Vargas, Eriberto, Ziller, Joseph W, Gorodetsky, Alon A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.01.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PROCESSABLE GRAPHENE NANORIBBONS
QUINOLINE
NANOGRAPHENE
CHEMISTRY
DERIVATIVES
SHEETS
BOTTOM-UP SYNTHESIS
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Summary:Graphene nanoribbons (GNRs) are promising candidate materials for the next generation of nanoscale electronics. Described herein is the synthesis of 2,4,6-substituted benzoquinolines, which constitute building blocks for nitrogen-doped GNRs. The presented facile and modular aza-Diels–Alder chemistry accommodates the installation of diverse functionalities at the crowded benzoquinolines’ 2 positions. Given the general utility of the benzoquinoline motif, these findings hold relevance not only for carbon-based electronics but also for a range of chemical disciplines.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02939