Comprehensive investigation of the excited-state dynamics of push-pull triphenylamine dyes as models for photonic applications

A series of emitting push-pull triarylamine derivatives, models of their widely used homologues in photonics and organic electronics, was investigated by steady-state and time-resolved spectroscopy. Their structural originality stems from the sole change of the electron-withdrawing substituent X (-H...

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Bibliographic Details
Published in:Physical chemistry chemical physics : PCCP 2013-01, Vol.15 (33), p.13922-13939
Main Authors: ISHOW, Eléna, CLAVIER, Gilles, MIOMANDRE, Fabien, REBARZ, Mateusz, BUNTINX, Guy, POIZAT, Olivier
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
Applied sciences
Charge transfer
Chemical Sciences
Chemistry
Circuit properties
Derivatives
Electric, optical and optoelectronic circuits
Electronics
Electrons
Emission
Emissivity
Exact sciences and technology
Excitation
Fluorescent Dyes - chemistry
General and physical chemistry
Integrated optics. Optical fibers and wave guides
Kinetics
Models, Molecular
Optical and optoelectronic circuits
or physical chemistry
Photons
Polarity
Quantum Theory
Quenching
Solvents
Solvents - chemistry
Spectrometry, Fluorescence
Theoretical and
Thermodynamics
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Summary:A series of emitting push-pull triarylamine derivatives, models of their widely used homologues in photonics and organic electronics, was investigated by steady-state and time-resolved spectroscopy. Their structural originality stems from the sole change of the electron-withdrawing substituent X (-H: 1, -CN: 2, -NO2: 3, -CHC(CN)2: 4), giving rise to efficient emission tuning from blue to red upon increasing the X electron-withdrawing character. All compounds are highly fluorescent in alkanes. The more polar compounds 2-4 undergo considerable Stokes shift and emission quenching in polar solvents. Femtosecond transient absorption data allowed us to identify the nature of the emissive state which varies as a function of the compound and surrounding polarity. A long-lived ππ* excited state with weak charge transfer character was found for 1. This excited state evolves into a long-lived ICT state with red-shifted emission for 2 in polar solvents. For 3 and 4, the ICT state is directly populated in all solvents. Long-lived and emissive in n-hexane, it relaxes in toluene to a new ICT' conformation with stronger charge transfer character and enhanced Stokes shift. In more polar THF, ethanol, and nitrile solvents, ICT relaxes to a dark excited state ICT'' with viscosity-dependent kinetics (
ISSN:1463-9076
1463-9084
DOI:10.1039/c3cp51480c