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Unexpected Photoluminescence of Fluorinated Naphthalene Diimides
Author(s) -
Maniam Subashani,
Cox Rosalind P.,
Langford Steven J.,
Bell Toby D. M.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405876
Subject(s) - quantum yield , photochemistry , fluorescence , molecule , chemistry , naphthalene , yield (engineering) , excitation , millisecond , carbazole , photoluminescence , materials science , optoelectronics , organic chemistry , quantum mechanics , physics , astronomy , electrical engineering , metallurgy , engineering
Two new amino core‐substituted naphthalene diimides (cNDIs) bearing fluorinated side chains have been synthesised. Steady‐state and time‐resolved fluorescence spectroscopy reveals unprecedented optical properties for the cNDIs with high quantum yields of ∼0.8 and fluorescence lifetimes of ∼13 ns in a range of solvents. These properties are apparent at the level of single molecules, where the compounds also show exceptional photostability under pulsed‐laser excitation. Photon emission is remarkably consistent with very few long timescale (millisecond or longer) interruptions with molecules regularly undergoing >10 7 cycles of excitation and emission. Intermittencies owing to triplet‐state formation occur on a sub‐millisecond timescale with a low yield of 1–2 %, indicating that the presence of the fluorine atoms does not lead to a significant triplet yield through the heavy‐atom effect. These properties make the compounds excellent candidates for single‐molecule labelling applications.