Reinvestigation of the Vilsmeier-Haack Formylation of Triphenylamine

Synlett (Impact Factor: 2.66). 11/1997; 1997(11):1275-1276. DOI: 10.1055/s-1997-1024
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    ABSTRACT: Three organic dyes, 2-cyano-3-(N-hexylphenothiazine-3-yl)acrylic acid (H-PTZ), 2-cyano-3-(5′-(2-(Nhexylphenothiazine-3-yl)vinyl)-2,2′-bithiophen-5-yl)acrylic acid (H-PTZ-BT), and 2-cyano-3-(5-(4-((4-(2-(N-hexylphenothiazine-3-yl)vinyl)phenyl)(phenyl)amino)phenyl)thiophen-2-yl)acrylic acid (H-PTZ-TPA-T), based on the phenothiazine (PTZ) unit as an electron donor moiety and cyanoacrylic acid unit as an electron acceptor moiety were synthesized to study the effect of a π-conjugated bridge of the dye on the performance of the resulting dye-sensitized solar cells devices. The thiophene unit and triphenylamine were introduced as a π-conjugated bridge. The H-PTZTPA-T-sensitized cell showed the highest overall conversion efficiency of 4.01% (J sc : 9.64 mA·cm−2; V oc : 0.69 V; FF: 0.60), while the H-PTZ-sensitized cell showed the lowest value of 3.57% (J sc : 7.76 mA·cm−2; V oc : 0.70 V; FF: 0.65) among the cells based on the three organic dyes compared to 5.09% for the cell based on the N719 dye (J sc : 12.77 mA·cm−2; V oc : 0.72 V; FF: 0.55) under AM 1.5 illumination (100 mW·cm−2).
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    ABSTRACT: In this high-technology application, age functional dyes especially polymethine dyes have captured much attention of the researchers due to their immense potential for high-tech uses. Polymethine dyes show promising absorption spectra in the visible range, which can be easily exploited for the use of written text copying, photographic imaging, or photothermographic recording materials. Keeping this in mind, our research is composed of an investigation of two triphenylamino-based polymethine dyes, a known polymethine dye 3 and a new one polymethine dye 5, which have been synthesized by the reaction of 4-(diphenylamino) benzaldehyde 2 and 4,-(phenylazanediyl) dibenzaldehyde 4 with 4,-vinylidene-bis(N, N-dimethylaniline) 1. Based on bis-dimethylaminophenylethylene moiety, the new polymethine dye showed more high absorption spectra in the range of 600–700 nm than that of the known polymethine dye based on bis-dimethylaminophenylethylene moiety. Their maximum spectra were exhibited at 637 nm and 653 nm, respectively. Their leuco-converted reversible colored forms were also investigated.
    Journal of Chemistry. 05/2013; 2013.
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    ABSTRACT: Six star-shaped oligomers containing triphenylamine (D1-D3) and benzene unit (D4-D6) as cores have been synthesized by Wittig condensation or Heck coupling reaction using aromatic aldehydes and triphenylphosphonium salts or aromatic halogenated compounds with vinyl triphenylamine. All oligomers have well-defined molecular structure and high purity. Characterization of the oligomers was made by FT-IR, (1)H-NMR spectroscopy, UV-Vis, and fluorescence spectroscopy. The electrochemical behavior was studied by cyclic voltammetry (CV). The cyclic voltammograms have revealed that oligomers undergo quasireversible or irreversible redox processes. The irreversible process is associated with electrochemical polymerization of oligomers by dimerization of unsubstituted triphenylamine groups. Thermal characterization was accomplished by TGA and DSC methods and evidenced that all oligomers were stable materials until 250°C and have formed stable molecular glasses after first heating scan.
    ISRN organic chemistry. 01/2012; 2012:976178.