Issue 13, 2019

Synthesis and characterisation of rylene diimide dimers using molecular handcuffs

Abstract

A strategy for positioning, and loosely connecting, molecules in close proximity using mechanically interlocked handcuffs is described. The strategy is demonstrated using rylene diimides, creating dimeric structures in which two components are linked through pillar[5]arene/imidazolium rotaxanes. Investigation of the resulting molecules demonstrates intriguing and new properties that arise from placing these redox active dye molecules together, allowing interactions, whilst allowing the molecules to separate as required. In particular we observe excimer emission from a perylene diimide dimer handcuff and the formation of an unusual radical anion π-dimer upon double reduction of the same molecule. The latter exhibits a unique visible absorption profile for a PDI-based molecule. We demonstrate the flexibility of our approach by making an unprecedented mixed perylene diimide/naphthalene diimide dimer which also reveals interactions between the two components. Our synthetic strategy facilitates the creation of unusual dimeric structures and allows the investigation of intermolecular interactions and the effects they have on electronic and magnetic properties.

Graphical abstract: Synthesis and characterisation of rylene diimide dimers using molecular handcuffs

Supplementary files

Article information

Article type
Edge Article
Submitted
11 Jan 2019
Accepted
15 Feb 2019
First published
15 Feb 2019
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, 3723-3732

Synthesis and characterisation of rylene diimide dimers using molecular handcuffs

L. Yang, P. Langer, E. S. Davies, M. Baldoni, K. Wickham, N. A. Besley, E. Besley and N. R. Champness, Chem. Sci., 2019, 10, 3723 DOI: 10.1039/C9SC00167K

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements