NDLI: Effect of substitution on the ultrafast deactivation of the excited state of benzo[b]thiophene-arylamines

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Effect of substitution on the ultrafast deactivation of the excited state of benzo[b]thiophene-arylamines

Content Provider	Royal Society of Chemistry (RSC)
Author	Queiroz, M.-J. R. P. Pina, J. Melo, J. Seixas de
Copyright Year	2016
Abstract	A complete and systematic study of the spectroscopic and photophysical properties of five novel diarylamines in the benzo[b]thiophene series (oligoanilines) was performed in solution at room (293 K) and low (77 K) temperature. The title compounds resulting from the link between one aniline unit with a benzo[b]thiophene unit (with two different methyl and methoxy substitution) were characterized using steady-state absorption, fluorescence and phosphorescence spectroscopy, as well as femto- to nano-second time resolved spectroscopies. The study involved the determination of the absorption, emission and triplet–triplet absorption together with all relevant quantum yields (fluorescence, phosphorescence, intersystem crossing, internal conversion and singlet oxygen yields), excited state lifetimes and the overall set of deactivation rate constants (kF, kIC and kISC). This study was further complemented with theoretical calculations, namely with the determination of the optimized ground-state molecular geometries for the diarylamines together with the prediction of the lowest vertical one-electron excitation energy and the relevant molecular orbital contours using DFT calculations. The DFT results were found to corroborate the observed charge-transfer character of the singlet excited state. The experimental results showed that the radiationless decay processes (internal conversion and intersystem-crossing) constitute the main excited state deactivation pathways and that substitution with methyl and methoxy groups induces significant changes in the spectroscopic and photophysical behaviour of these compounds. This was also corroborated by the femtosecond transient absorption study, where it was found that the ultrafast dynamics of the diarylamines was best described by a sequential model featuring fast solvent relaxation followed by conformational relaxation to a more planar excited state, from where singlet excited state deactivation occurs through internal conversion and competitive intersystem crossing (the latter giving rise to the formation of long lived triplet states). The high singlet oxygen quantum yield values obtained suggest that the triplet state is involved in the photodegradation processes of these compounds.
Starting Page	1029
Ending Page	1038
Page Count	10
File Format	HTM / HTML PDF
ISSN	1474905X
Volume Number	15
Issue Number	8
Journal	Photochemical & Photobiological Sciences
DOI	10.1039/c6pp00140h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Molecular orbital Femtosecond Photodegradation Spectroscopy Fluorescence Thiophene Femto- Singlet oxygen Aniline Phosphorescence Intersystem crossing Internal conversion Solvent Methoxy group
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry

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