Fluorescence Quenching of 4,4′-Dimethoxytriphenylamine-Substituted Diketopyrrolopyrrole via Intramolecular Photoinduced Electron Transfer

Tae Gyu Hwang, Gi Rim Han, Jae Moon Lee, Jong Woo Lee, Hong Mo Kim, Doyk Hwang, Seong Keun Kim, Jae Pil Kim

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Abstract

Herein, we report significant fluorescence quenching induced by intramolecular photoinduced electron transfer (PET) in electron donor-acceptor-type π-conjugated organic molecules with methoxy-containing donor moieties. The fluorescence quenching of the diketopyrrolopyrrole (DPP, a well-known highly emissive luminophore) derivatives seemed to be affected by the methoxy moieties. Steady-state optical properties of the synthesized materials were analyzed in the solution, aggregate (N-methyl-2-pyrrolidone/H2O), and solid states in order to understand the influence of the surrounding environment. The mechanistic aspect of the intramolecular PET process in methoxy-containing DPP derivatives was revealed by singlet oxygen generation measurements and ultrafast femtosecond transient absorption spectroscopy. These results could provide crucial insights toward designing emissive π-conjugated organic molecules.

Original languageEnglish
JournalJournal of Physical Chemistry C
Volume123
Issue number39
DOIs
StatePublished - 3 Oct 2019

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