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.

/pdf/modulation-of-charge-transfer-by-n-alkylation-to-control-3nuqees2mz.pdf

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

Author(s): Bai, Shuming; Balevicius, Vytautas; Bittner, Eric; Cheng, Yuan-Chung; Chergui, Majed; Cina, Jeffrey; das Neves Rodrigues, Natercia; Datta, Animesh; Dawlaty, Jahan; Dodin, Amro; Fingerhut, Benjamin; Fleming, Graham; Ginsberg, Naomi; Hammes-Schiffer, Sharon; Huxter, Vanessa; Kohler, Bern; Lee, Yumin; Leggett, Graham; Marcus, Andrew; Morenz, Karen; Ogilvie, Jennifer; Olaya-Castro, Alexandra; Oliver, Thomas AA; Son, Minjung; Song, Yin; Stavros, Vasilios

/pdf/energy-and-charge-transfer-in-natural-photosynthesis-general-4ehusdtbuy.pdf

Energy and charge-transfer in natural photosynthesis: general discussion

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Energy and charge-transfer in natural photosynthesis: general discussion