A.T. Turley
Modulation of Charge Transfer by N-Alkylation to Control Photoluminescence Energy and Quantum Yield
Turley, A.T.; Danos, A.; Prlj, A.; Monkman, A.P.; Curchod, B.F.E.; McGonigal, P.R.; Etherington, M.K.
Authors
Dr Andrew Danos andrew.danos@durham.ac.uk
Senior Experimental Officer
A. Prlj
A.P. Monkman
B.F.E. Curchod
Dr Paul Mcgonigal paul.mcgonigal@durham.ac.uk
Academic Visitor
M.K. Etherington
Abstract
Charge transfer in organic fluorophores is a fundamental photophysical process that can be either beneficial, e.g., facilitating thermally activated delayed fluorescence, or detrimental, e.g., mediating emission quenching. N-Alkylation is shown to provide straightforward synthetic control of the charge transfer, emission energy and quantum yield of amine chromophores. We demonstrate this concept using quinine as a model. N-Alkylation causes changes in its emission that mirror those caused by changes in pH (i.e., protonation). Unlike protonation, however, alkylation of quinine’s two N sites is performed in a stepwise manner to give kinetically stable species. This kinetic stability allows us to isolate and characterize an N-alkylated analog of an ‘unnatural’ protonation state that is quaternized selectively at the less basic site, which is inaccessible using acid. These materials expose (i) the through-space charge-transfer excited state of quinine and (ii) the associated loss pathway, while (iii) developing a simple salt that outperforms quinine sulfate as a quantum yield standard. This N-alkylation approach can be applied broadly in the discovery of emissive materials by tuning charge-transfer states.
Citation
Turley, A., Danos, A., Prlj, A., Monkman, A., Curchod, B., McGonigal, P., & Etherington, M. (2020). Modulation of Charge Transfer by N-Alkylation to Control Photoluminescence Energy and Quantum Yield. Chemical Science, 11(27), 6990-6995. https://doi.org/10.1039/d0sc02460k
Journal Article Type | Article |
---|---|
Acceptance Date | Jun 8, 2020 |
Online Publication Date | Jun 9, 2020 |
Publication Date | Jul 21, 2020 |
Deposit Date | Jun 9, 2020 |
Publicly Available Date | Jun 9, 2020 |
Journal | Chemical Science |
Print ISSN | 2041-6520 |
Electronic ISSN | 2041-6539 |
Publisher | Royal Society of Chemistry |
Peer Reviewed | Peer Reviewed |
Volume | 11 |
Issue | 27 |
Pages | 6990-6995 |
DOI | https://doi.org/10.1039/d0sc02460k |
Public URL | https://durham-repository.worktribe.com/output/1269155 |
Related Public URLs | https://chemrxiv.org/articles/Modulation_of_Charge_Transfer_by_N-Alkylation_to_Control_Photoluminescence_Energy_and_Quantum_Yield/12159114/1 |
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