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Modulation of charge transfer by N-alkylation to control photoluminescence energy and quantum yield

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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 analogue 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.

Graphical abstract: Modulation of charge transfer by N-alkylation to control photoluminescence energy and quantum yield

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Article information


Submitted
30 Apr 2020
Accepted
08 Jun 2020
First published
09 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Modulation of charge transfer by N-alkylation to control photoluminescence energy and quantum yield

A. T. Turley, A. Danos, A. Prlj, A. P. Monkman, B. F. E. Curchod, P. R. McGonigal and M. K. Etherington, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC02460K

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