- Construction of 3,7-Dithienyl Phenothiazine-Based Organic Dyes via Multistep Direct C-H Arylation Reactions
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Herein, an effective and feasible approach to prepare 3,7-dithienyl phenothiazine-based organic dyes has been developed. In this synthetic procedure, the Pd-catalyzed multistep direct C-H arylation of thiophene derivatives with phenothiazine bromides was employed for the first time to construct the 3,7-dithienyl phenothiazine core scaffold, which greatly streamlines access to this class of organic dyes. 3-Thienyl phenothiazine-based dyes were also synthesized via the direct C-H arylation of thiophenes as references. Most of the 3,7-dithienyl phenothiazine-based dyes exhibit better photovoltaic performances than the 3-thienyl phenothiazine-based dyes. Among these organic dyes, the solar cell device based on 6d exhibits the highest conversion efficiency of 8.9%. Compared with 6d, organic dyes with longer π-conjugation, also including bithiophene as the π-spacer, show dramatically reduced conversion efficiencies of cell devices. The introduction of the more electron-rich 3,4-ethylenedioxythiophene to the C3- and/or C7-position of phenothiazine instead of thiophene does not significantly improve the photoelectric conversion performance. The highly efficient synthetic strategy herein developed and these primary results may be helpful to design and synthesize a variety of new 3,7-dithienyl phenothiazine-based organic dyes.
- Wang, Wen,Li, Xiaoyu,Lan, Jingbo,Wu, Di,Wang, Ruilin,You, Jingsong
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- Red electroluminescent micromolecule and preparation method thereof
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The invention belongs to the technical field of photoelectric display devices, and relates to a red electroluminescent micromolecule and a preparation method thereof. The structural formula of the red electroluminescent micromolecule provided by the invention is shown in (I); and in the formula, R is a straight chain or branched chain alkyl group or alkoxy group or H atom or aryl group with the carbon atom number of 1-20. The preparation method of the red electroluminescent micromolecule which comprises the following step that: (2-(4-aminobenzoyl)-2 ', 7'-bis (3, 6-di-tert-butyl-9H-carbazole-9-yl)-9, 9 '-spirobis [fluorene]-7-yl) (4-(3, 6-di-tert-butyl-9H-carbazole-9-yl) phenyl) ketone reacts with a compound as shown in a formula (II) to obtain the compound as shown in the formula (I). According to the preparation method of the invention, the technical problems of lack of spirofluorene-based red fluorescent photoelectric materials, low fluorescent quantum yield and low device efficiency in the prior art are solved.
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Paragraph 0034-0036
(2021/07/31)
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- Green light compound based on dibenzophenazine, preparation method and device thereof
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The invention belongs to the technical field of photoelectric display devices, and particularly relates to a green light compound based on dibenzophenazine, a preparation method and a device thereof. The invention provides the green light compound based o
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Paragraph 0039-0041
(2021/08/07)
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- Phenanthroimidazole-based blue light bipolar small molecule and preparation method thereof
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The invention relates to the technical field of photoelectric display devices, in particular to a phenanthroimidazole-based blue light bipolar small molecule and a preparation method thereof. The invention provides the phenanthroimidazole-based blue light bipolar small molecule. The chemical formula of the blue light bipolar small molecule is shown as a formula (I). The invention also provides a preparation method of the blue light bipolar small molecule based on phenanthroimidazole, and the preparation method comprises the following steps: carrying out a reaction on the compound shown in the formula (II) and 1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxo boron ester-2-yl)phenyl)-1H-phenanthroimidazole to prepare the small molecule shown in the formula (I). The invention provides the phenanthroimidazole-based blue light bipolar small molecule and the preparation method thereof, and solves the technical problems that the prior art lacks a phenanthroimidazole fluorescent photoelectric material, cannot give consideration to hole and electron transmission efficiency, and is low in device efficiency.
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Paragraph 0026-0028
(2021/10/20)
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- A high-contrast photoacoustic agent with near-infrared emission
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Benzobisthiadiazole as a typical electron acceptor, has been widely used to design fluorescent dyes and photoacoustic (PA) agents. With the strategy of constructing donor-acceptor-donor (D-A-D) type of electron characteristics, benzobisthiadiazole derivatives tend to behave stable in near-infrared absorption and emission, which is beneficial to PA imaging. In this chapter, two molecular design strategies are combined to improve the photoacoustic imaging effects of new PA contrast agent IR-1302 NPs, by installing strengthened conjugated bridges and electron donors. The nanoparticles exhibit high-contrast noninvasive photoacoustic imaging in tumor models with longer wavelength absorption and emission and show potential as a clinic contrast agent.
- Chen, Weijie,Ye, Fengying,Yin, Jun,Yang, Guang-Fu
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p. 223 - 247
(2021/07/26)
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- Chemistry of polyhalogenated nitrobutadienes, part 11: Ipso-formylation of 2-chlorothiophenes under Vilsmeier-Haack conditions
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The regioselective ipso-formylation of electron-rich, 3,4-push-pull- substituted 2-chlorothiophenes under Vilsmeier-Haack conditions was performed in good yields. The synthetic scope of this new reaction was explored using various halothiophenes, chloroanilines, and 1-methyl-3-chloroindole. In comparison with their structural C-H analogs the chlorinated thiophenes, anilines, and the indole proved to be less reactive toward electrophilic attack by chloromethyleniminium salts.
- Vogt, Eva-Janina,Zapol'skii, Viktor A.,Nutz, Eva,Kaufmann, Dieter E.
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experimental part
p. 285 - 294
(2012/07/14)
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- Theoretical and experimental investigations of the spectroscopic and photophysical properties of fluorene-phenylene and fluorene-thiophene derivatives: precursors of light-emitting polymers
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The ground and excited states of covalently linked fluorene-based dimers were investigated by theoretical methods and by UV-vis and fluorescence spectroscopies. The optimized structures and the characterization of frontier molecular orbitals were obtained by HF/6-31G* ab initio calculations. All derivatives are nonplanar in their ground electronic states. The extent of nonplanarity depends on the nature of the aromatic ring bonded to the fluorene unit. All frontier orbitals involved both subunits of the dyads. The HOMO of each compound possesses an antibonding character between subunits, while the LUMO shows bonding character. The nature and the energy of the first 10 singlet-singlet electronic transitions have been obtained by ZINDO/S semiempirical calculations performed on the HF/6-31G* optimized geometries. All electronic transitions are of the ππ* type and involve both subunits of the molecules. For each derivative, excitation to the S1 state corresponds mainly to the promotion of an electron from the HOMO to the LUMO, and the S1 ← S0 electronic transition is strongly favored and polarized along the long axis of the molecular frame. The energy of the first electronic transition of all derivatives follows the HOMO-LUMO energy gap computed from HF/6-31G* ab initio calculations. The absorption and fluorescence spectra of the fluorene derivatives have been recorded in cyclohexane. The first absorption band of each derivative can be assigned to the S1 ← S0 electronic transition computed from ZINDO/S calculations. The overall shape of the absorption and fluorescence spectra suggests a smaller distribution of conformers in the S1 state than in the ground state. The fluorescence quantum yield and lifetime in cyclohexane have been obtained. In these systems, the photophysical properties are mainly governed by nonradiative processes.
- Belletete, Michel,Beaupre, Serge,Bouchard, Jimmy,Blondin, Pierre,Leclerc, Mario,Durocher, Gilles
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p. 9118 - 9125
(2007/10/03)
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