Structural modelling of optical and electrochemical properties of 4-aminodiphenylamines - optoelectronic studies on a polyaniline repeating unit

Amino-diphenylanilines and their planarized and twisted model compounds have been investigated by steady state and time-resolved absorption and emission, as well as by spectroelectrochemistry. These polyaniline model compounds show that the observation of excited states with full charge separation i...

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Bibliographic Details
Published in:Photochemical & photobiological sciences 2004-10, Vol.3 (10), p.939-948
Main Authors: Malval, Jean Pierre, Morand, Jean Pierre, Lapouyade, René, Rettig, Wolfgang, Jonusauskas, Gediminas, Oberlé, Jean, Trieflinger, Christian, Daub, Joerg
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
Electrochemistry - methods
Electronics
Hydrogen-Ion Concentration
Models, Chemical
Molecular Structure
Optics
Optics and Photonics
Oxidation-Reduction
Phenylenediamines - chemistry
Physics
Spectrometry, Fluorescence - methods
Spectrophotometry, Atomic - methods
Time Factors
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Summary:Amino-diphenylanilines and their planarized and twisted model compounds have been investigated by steady state and time-resolved absorption and emission, as well as by spectroelectrochemistry. These polyaniline model compounds show that the observation of excited states with full charge separation is linked to molecular twisting where the diaminobenzene is the donor and the phenyl group the acceptor. The observable charge transfer fluorescence shows the characteristic features of twisted intramolecular charge transfer (TICT) excited states, i.e. forbidden emissive properties and strong solvatochromic red shift. The transient absorption spectrum of the TICT state matches the ground state absorption spectrum of the electrochemically produced radical cation of the molecule. This is the first example where excited-state properties of the neutral and ground state properties of the radical cation are directly linked.
ISSN:1474-905X
1474-9092
DOI:10.1039/b406519k