Ground and Excited States of Bis‐4‐Methoxybenzyl‐Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies

Murphy, Alanna S.; Killalea, C. Elizabeth; Humphreys, Joshua; Hume, Paul A.; Cliffe, Matthew J.; Murray, Glen J.; Davies, E. Stephen; Lewis, William; Amabilino, David B.

Abstract

A series of symmetrically bis‐4‐methoxybenzyl (4MB) N‐substituted 1,4‐diketopyrrolo[3,4‐c]pyrrole (DPP) derivatives have been synthesized. The 4MB unit makes the DPP core soluble, and shows subtle modification of up to 0.2 eV in ground and excited states of the core when compared with related alkyl derivatives. Absorption and emission spectroscopy, as well as electrochemical and computational methods have been employed to prove the importance of the peripheral aryl units on the donor/ acceptor properties of the molecules. The 4MB products are highly fluorescent (quantum yields approaching 100 % in solution), with a unique distribution of frontier states shown by spectroelectrochemistry. The solid‐state fluorescence correlates with the X‐ray crystal structures of the compounds, a Stokes shift of approximately 80 nm is seen for two of the compounds. The frontier energy levels show that this subtle substitutional change could be of future use in molecular energy level tailoring in these, and related, materials for organic (opto)electronics.

Citation

Murphy, A. S., Killalea, C. E., Humphreys, J., Hume, P. A., Cliffe, M. J., Murray, G. J., Davies, E. S., Lewis, W., & Amabilino, D. B. (2019). Ground and Excited States of Bis‐4‐Methoxybenzyl‐Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies. ChemPlusChem, 84(9), 1413-1422. https://doi.org/10.1002/cplu.201900286

• Journal Article Type: Article
• Acceptance Date: Jul 15, 2019
• Online Publication Date: Jul 31, 2019
• Publication Date: 2019-09
• Deposit Date: Sep 30, 2019
• Publicly Available Date: Aug 1, 2020
• Journal: ChemPlusChem
• Electronic ISSN: 2192-6506
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 84
• Issue: 9
• Pages: 1413-1422
• DOI: https://doi.org/10.1002/cplu.201900286
• Public URL: https://nottingham-repository.worktribe.com/output/2469438
• Publisher URL: https://onlinelibrary.wiley.com/doi/full/10.1002/cplu.201900286
• Additional Information: This is the peer reviewed version of the following article: A. S. Murphy, C. E. Killalea, J. Humphreys, P. A. Hume, M. J. Cliffe, G. J. Murray, E. S. Davies, W. Lewis, D. B. Amabilino, ChemPlusChem 2019, 84, 1413, which has been published in final form at https://doi.org/10.1002/cplu.201900286. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.; ; Received: 2019-05-03; Published: 2019-07-31
• Contract Date: Sep 30, 2019