Issue 24, 2010

Core-substituted naphthalenediimides


This feature article reviews research of core-substituted naphthalenediimides (cNDIs) in a comprehensive yet easily readable manner. Their synthesis, electrochemistry and spectroscopy are covered first with emphasis on the ability of cNDIs with electron donating substituents to absorb and fluoresce in all colors without global structural changes and cNDIs with electron withdrawing substituents to reach unprecedented extents of π-acidity. The section on supramolecular chemistry covers face-to-face π-stacks and peripheral hydrogen bonds, that on molecular recognition moves from pH and fluoride sensors to the binding to telomeric DNA in vivo and intercalation into π-stacks and sticky tweezers. cNDIs can recognize and transport anions by functional anion–π interactions. The section on electron transport describes cNDIs as air-stable n-semiconductors with high charge mobility and use as OFETs. Photoinduced electron transport by rainbow cNDIs has been used for the creation of artificial photosystems in solution, in bilayer membranes and on solid substrates. Examples include multicolor light harvesting architectures, organic solar cells, photosystems that can open up into ion channels, and supramolecular n/p-heterojunctions with antiparallel redox gradients. The review is highly interdisciplinary but should appeal most to organic, biosupramolecular and physical chemists.

Graphical abstract: Core-substituted naphthalenediimides

Article information

Article type
Feature Article
23 Feb 2010
07 Apr 2010
First published
14 May 2010

Chem. Commun., 2010,46, 4225-4237

Core-substituted naphthalenediimides

N. Sakai, J. Mareda, E. Vauthey and S. Matile, Chem. Commun., 2010, 46, 4225 DOI: 10.1039/C0CC00078G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity