Issue 4, 2019

Defying strain in the synthesis of an electroactive bilayer helicene

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

Supplementary files

Article information

Article type
Edge Article
Submitted
21 9 2018
Accepted
09 11 2018
First published
20 11 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 1029-1034

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. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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