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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


IMPACT FACTOR 2018: 2.350
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1365-3075
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Volume 89, Issue 11

Issues

Stereochemical implications toward the total synthesis of aromatic belts

Matthew R. Golder
  • Corresponding author
  • Department of Chemistry and Biochemistry and Material Science Institute, University of Oregon, Eugene, OR 97403, USA
  • Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Lev N. Zakharov
  • CAMCOR – Center for Advanced Materials Characterization in Oregon, University of Oregon, Eugene, OR 97403, USA
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  • De Gruyter OnlineGoogle Scholar
/ Ramesh Jasti
  • Department of Chemistry and Biochemistry and Material Science Institute, University of Oregon, Eugene, OR 97403, USA
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Published Online: 2017-09-09 | DOI: https://doi.org/10.1515/pac-2017-0413

Abstract

The synthesis of carbon nanotube (CNT) fragments has long captivated organic chemists, despite the simplistic, symmetric nature of the requisite achiral targets. Such molecules hold the potential to allow for the synthesis of homogeneous CNTs, rendering their properties more suitable for advanced applications in electronics and sensing. The [n]cycloparaphenylene family, comprised of molecules with para-linked phenyl rings in a contiguous macrocycles, represents a major landmark towards achieving absolute control of CNT architecture from the bottom-up. Attempts towards accessing the [n]cyclacene and [n]cyclophenacene families, both of which are comprised of double-stranded macrocyclic belts, have only recently been successful, however. These targets have been plagued by unstable, strained intermediates and stereochemical pitfalls that have largely thwarted accessing these fascinating structures. Herein, we disclose our synthetic strategy toward overcoming several stereochemical challenges en route to [n]cyclophenacenes via highly substituted [n]cycloparaphenylene precursors.

This article offers supplementary material which is provided at the end of the article.

Keywords: carbon nanotubes; chirality; cyclophanes; diastereoselectivity; IUPAC-SOLVAY International Award for Young Chemists; macrocycles; polycyclic aromatics

Article note:

A collection of peer-reviewed articles by the winners of the 2016 IUPAC-SOLVAY International Award for Young Chemists.

References

About the article

Published Online: 2017-09-09

Published in Print: 2017-10-26


Citation Information: Pure and Applied Chemistry, Volume 89, Issue 11, Pages 1603–1617, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2017-0413.

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©2017 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/.Get Permission

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[1]
Mark C. Cesa and Hugh D. Burrows
Pure and Applied Chemistry, 2018, Volume 0, Number 0

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