UCL Discovery
UCL home » Library Services » Electronic resources » UCL Discovery

Doubly Encapsulated Perylene Diimides: Effect of Molecular Encapsulation on Photophysical Properties

Royakkers, J; Minotto, A; Congrave, DG; Zeng, W; Patel, A; Bond, AD; Bučar, D-K; ... Bronstein, H; + view all (2020) Doubly Encapsulated Perylene Diimides: Effect of Molecular Encapsulation on Photophysical Properties. The Journal of Organic Chemistry , 85 (1) pp. 207-214. 10.1021/acs.joc.9b02597. Green open access

[thumbnail of acs.joc.9b02597.pdf]
Preview
Text
acs.joc.9b02597.pdf - Accepted Version

Download (1MB) | Preview

Abstract

Intermolecular interactions play a fundamental role on the performance of conjugated materials in organic electronic devices, as they heavily influence their optoelectronic properties. Synthetic control over the solid state properties of organic optoelectronic materials is crucial to access real life applications. Perylene diimides (PDIs) are one of the most highly studied classes of organic fluorescent dyes. In the solid state, π–π stacking suppresses their emission, limiting their use in a variety of applications. Here, we report the synthesis of a novel PDI dye that is encapsulated by four alkylene straps. X-ray crystallography indicates that intermolecular π–π stacking is completely suppressed in the crystalline state. This is further validated by the photophysical properties of the dye in both solution and solid state and supported by theoretical calculations. However, we find that the introduction of the encapsulating “arms” results in the creation of charge-transfer states which modify the excited state properties. This article demonstrates that molecular encapsulation can be used as a powerful tool to tune intermolecular interactions and thereby gain an extra level of control over the solid state properties of organic optoelectronic materials.

Type: Article
Title: Doubly Encapsulated Perylene Diimides: Effect of Molecular Encapsulation on Photophysical Properties
Location: United States
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/acs.joc.9b02597
Publisher version: https://doi.org/10.1021/acs.joc.9b02597
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: Dyes and pigments, Hydrocarbons, Thin films, Encapsulation, Aromatic compounds
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Physics and Astronomy
URI: https://discovery.ucl.ac.uk/id/eprint/10086320
Downloads since deposit
96Downloads
Download activity - last month
Download activity - last 12 months
Downloads by country - last 12 months

Archive Staff Only

View Item View Item