Jump to main content
Jump to site search

Issue 4, 2019
Previous Article Next Article

Defying strain in the synthesis of an electroactive bilayer helicene

Author affiliations

Abstract

We report the synthesis of a bilayer chiral nanographene incorporating a [7]helicene scaffold and two perylene-diimide (PDI) subunits. Twofold visible-light-induced oxidative cyclization of a phenanthrene framework selects for the desired PDI-helicene, despite the immense strain that distinguishes this helicene from two other accessible isomers. This strain arises from the extensive intramolecular overlap of the PDI subunits, which precludes racemization, even at elevated temperatures. Relative to a smaller homologue, this PDI-helicene exhibits amplified electronic circular dichroism. It also readily and reversibly accepts four electrons electrochemically. Modifications to the core phenanthrene subunit change the fluorescence and electrochemistry of the PDI-helicene without significantly impacting its electronic circular dichroism or UV-visible absorbance.

Graphical abstract: Defying strain in the synthesis of an electroactive bilayer helicene

Back to tab navigation

Supplementary files

Article information


Submitted
21 Sep 2018
Accepted
09 Nov 2018
First published
20 Nov 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 1029-1034
Article type
Edge Article

Defying strain in the synthesis of an electroactive bilayer helicene

M. Milton, N. J. Schuster, D. W. Paley, R. Hernández Sánchez, F. Ng, M. L. Steigerwald and C. Nuckolls, Chem. Sci., 2019, 10, 1029
DOI: 10.1039/C8SC04216K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements