Novel poly(triphenylamine-alt-fluorene) with asymmetric hexaphenylbenzene and pyrene moieties: synthesis, fluorescence, flexible near-infrared electrochromic devices and theoretical investigationElectronic supplementary information (ESI) available. See DOI: 10.1039/c5py01971k
In this study, a new triphenylamine- alt -fluorene conjugated copolymer, HPBPYFL6 , with hexaphenylbenzene (HPB) and pyrene as asymmetrical pendant groups was synthesized via Suzuki coupling polymerization. The conjugated polymer had a weight-average molecular weight of 5.8 × 10 4 g mol −1 with a po...
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Main Authors | , , , , |
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Format | Journal Article |
Published |
09.02.2016
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Online Access | Get full text |
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Summary: | In this study, a new triphenylamine-
alt
-fluorene conjugated copolymer,
HPBPYFL6
, with hexaphenylbenzene (HPB) and pyrene as asymmetrical pendant groups was synthesized
via
Suzuki coupling polymerization. The conjugated polymer had a weight-average molecular weight of 5.8 × 10
4
g mol
−1
with a polydispersity index of 2.5 characterized by gel permeation chromatography (GPC).
HPBPYFL6
showed good solubility in common organic solvents such as NMP, THF, toluene and dichloromethane at 25 °C. In addition,
HPBPYFL6
possessed a high glass transition temperature of 260 °C and a 10% weight-loss temperature of 503 °C in nitrogen.
HPBPYFL6
bearing a pyrene moiety had a solvatochromic fluorescence shift from a green to an orange emission as the polarity of the solvent increased. Cyclic voltammetry of
HPBPYFL6
films cast onto indium-tin oxide-coated glass (ITO-glass) exhibited two oxidation redox couples at an
E
1/2
value of 0.82 and 1.17 V
versus
Ag/Ag
+
in an acetonitrile solution. The
HPBPYFL6
film on graphene-coated PET had an
E
1/2
value of 0.24 and 1.12 V. Conjugated polymer films exhibited reversible electrochromic behaviour with a colour change from pale yellow to deep blue upon electrochemical oxidation and high absorbance in the near-infrared (NIR) region. The switching and bleaching times were 5.16 s and 3.12 s for 1231 nm and were 3.30 s and 3.74 s for 1030 nm of
HPBPYFL6
on ITO-glass. The strong NIR electrochromic absorbance of
HPBPYFL6
was attributed to intervalence charge transfer by the incorporation of the HPB moiety. This phenomenon was confirmed by chemical oxidation as the oxidant contents increased in the solution state. Furthermore, the electrochromic mechanism was interpreted by DFT calculation and the simulated NIR electrochromic spectra of model compound
HPBPYFL
are in good agreement with the experimental data.
A new triphenylamine-
alt
-fluorene conjugated polymer with hexaphenylbenzene and pyrene for near-infrared electrochromism supported by DFT calculation and simulated spectra. |
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Bibliography: | 10.1039/c5py01971k Electronic supplementary information (ESI) available. See DOI |
ISSN: | 1759-9954 1759-9962 |
DOI: | 10.1039/c5py01971k |