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    An unexpected discovery of a one-pot synthesis for carbazole-based diamine and the electrochromic properties of the derived polymers
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    Abstract:
    Carbazole-based diamines, E-Cz or K-Cz, were unexpectedly synthesized via the hydrogenation reaction in one pot, where the reduction of the nitro group, the deprotection of the benzyl group, and the coupling of triphenylamine happen simultaneously.
    Keywords:
    Carbazole
    Triphenylamine
    Coupling reaction
    The 2,7- and 3,6-substituted carbazole and triphenylamine chalcogenophene (Se, Te) derivatives and their electrodeposited polymers are investigated using electrochemical and UV–vis–NIR/ESR spectroelectrochemical methods. Major differences in the case of oxidation and electropolymerization behavior between monomers and related polymers are shown. Se and Te atoms do not conjugate their lone electron pairs with the π-conjugated system and therefore only increase the contribution of the quinoid form of the chalcogenophene unit. The 2,7- substituted carbazole derivatives present stronger carbazole–chalcogenophene conjugation than 3,6-substituted derivatives. One 3,6-substituted carbazole derivative and triphenylamine derived polymers were found to have promising electrochromic properties with black electrochromism.
    Triphenylamine
    Carbazole
    Lone pair
    Citations (27)
    Two novel triphenylamine-containing thiophene derivative monomers, 4-methoxy-4',4''-di(thiophen-2-yl)triphenylamine (MTTPA) and 4-methoxy-4',4''-di(2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)triphenylamine (METPA), were successfully synthesized. The corresponding polymers including PMTTPA and PMETPA were electrochemically synthesized and characterized by cyclic voltammetry (CV), UV–vis–NIR spectroscopy and scanning electron microscopy (SEM). Electrochemical and spectroelectrochemical analysis showed that two polymers had reversible redox behavior and multi-electrochromic property. Dynamic electrochromic experiments suggested that both the polymers had rapid switching time, high coloration efficiency, and high contrast of optical transmittance changes (ΔT%) in the NIR region (55.5% at 1280 nm for PMTTPA, 77.6% at 1200 nm for PMETPA). The dual-type electrochromic device based on PMTTPA film (or PMETPA film) was constructed and characterized as well. Both of them revealed excellent properties.
    Triphenylamine
    Electrochromic devices
    Citations (7)
    Carbazole, triphenylamine and thiophene derivatives have received great interest due to their outstanding electrochemical and electrochromic performance. In this study, four novel monomers based on carbazole-thiophene and triphenylamine derivatives (BTC-TPA, BTC-DMTPA, DTC-TPA and DTC-DMTPA) were synthesized and characterized. The obtained monomers could form corresponding polymer films on the surface of ITO/glass electrode by electropolymerization. Electrochemical properties and morphology of the polymer films were investigated. Spectroelectrochemical measurements demonstrated that the polymer films could exhibit multi-color electrochromism, especially for P(DTC-TPA) film, which could show four different colors(brown-green, blue gray, blue and purple black) at different redox states. Moreover, all the polymer films also possessed good optical contrast, reasonable switching time and coloration efficiency. These finding implied that the obtained polymer films could be considered as good candidates for the opto-electronic applications.
    Triphenylamine
    Carbazole
    Electrochromic devices
    Citations (5)