A facile and highly efficient green synthesis of carbazole derivatives containing a six-membered ring

Wang, Haowei; Chen, Yu; Ye, Wenbo; Xu, Jingkun; Liu, Daofu; Yang, Jiaxiang; Kong, Lin; Zhou, Hongping; Tian, Yupeng; Tao, Xutang

doi:10.1016/j.dyepig.2012.11.009

Cited by 9 publications

(4 citation statements)

References 48 publications

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“…We first described the formation of cyclohexane-1,3-diols from the condensation of 2-acetylpyridine with benzaldehyde derivatives in 1995 [58]. Although less commonly observed than the 3:2 condensation products, compounds of this type, arising from the aldol condensation of an intermediate pentane-1,5-dione with a third equivalent of ketone, have been isolated with a variety of substituents [32,60,68,69,70,71,72,73]. The relative stereochemistry in 10 , originally proposed on the basis of NMR studies [58], has been crystallographically confirmed [32,69,70,72].…”

Section: Review Of Literaturementioning

confidence: 99%

Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong?

Rocco¹,

Housecroft²,

Constable³

2019

Molecules

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The preparation of 24-functionalized 12,22:26,32-terpyridines (4′-functionalized 3,2:6′,3″-terpyridines) by the reaction of three 4-alkoxybenzaldehydes with 3-acetylpyridine and ammonia was investigated; under identical reaction conditions, two (R =nC4H9, C2H5) gave the expected products whereas a third (R = nC3H7) gave only a cyclohexanol derivative derived from the condensation of three molecules of 3-acetylpyridine with two of 4-(n-propoxy)benzaldehyde. A comprehensive survey of “unexpected” products from reactions of ArCOCH3 derivatives with aromatic aldehydes is presented. Three different types of alternative product are identified.

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Section: Review Of Literaturementioning

confidence: 99%

Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong?

Rocco¹,

Housecroft²,

Constable³

2019

Molecules

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“…For background to the applications of carbazoles, see: Wang et al (2013); Feng et al (2013); Park et al (2015). For further synthetic details, see: Zhang et al (2014).…”

Section: Related Literaturementioning

confidence: 99%

“…The title compound is a carbazole derivative with an amine group and a pyridine group. Carbazole is usually utilized in organic functional materials due to it is a large conjugated system with prominent hole-transporting (Wang et al, 2013).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 9-butyl-6-[2-(pyridin-4-yl)ethenyl]carbazol-3-amine

2015

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The asymmetric unit of the title compound, C23H23N3, consists of two molecules, A and B, with different conformations. In molecule A, the dihedral angle between the carbazole ring system (r.m.s. deviation = 0.028 Å) and the pyridine ring is 20.28 (9)° and the N—C—C—C torsion angle of the butyl side chain is −63.4 (3)°. The equivalent data for molecule B are 0.065 Å, 48.28 (11)° and 61.0 (3)°, respectively. In the crystal, the components are connected by weak N—H⋯N hydrogen bonds, generating [030] C(14) chains of alternating A and B molecules.

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“…Metal-free organic dyes have been utilized as sensitizers of TiO 2 with a visible-light response because of their advantages of having high molar absorption coefficients, wide absorption bands, facile molecular designs, and a lack of concern with noble-metal resources. − Squaraine dyes (SQs) are a class of promising dyes with resonance-stabilized zwitterionic structure because of their strong absorption arising from charge transfer between the electron-deficient central four-membered ring and oxygen moieties, with contributions from substituents on both sides. Sensitizers with sharp and intense absorption bands in the visible and near-IR regions are needed in electrography, organic photovaltaic materials, and optical data storage applications. − SQs have been employed in different cutting-edge technologies such as nonlinear optics, photodynamic therapy, or biolabeling applications.…”

Section: Introductionmentioning

confidence: 99%

Effect of Dye Structure on Optical Properties and Photocatalytic Behaviors of Squaraine-Sensitized TiO₂ Nanocomposites

Fang

Yang

et al. 2014

J. Phys. Chem. C

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TiO 2 nanoparticles obtained by an improved polymerization-induced colloid aggregation (Im-PICA) method were sensitized by three squaraine dyes to construct dye/TiO 2 nanocomposite photocatalysts (1:3 mass ratios) with visible-light responses by a facile hydrothermal method. Scanning electron microscopy (SEM) and transmission electron miscroscopy (TEM) were employed to visually observe the surface morphologies of the samples. We studied the visible-light response using UV−vis diffuse reflectance spectroscopy and optical band gap calculations using the Tauc plot equation. The dyes exhibit excellent thermal stability, which is ascribed to the decomposition temperature reaching 300 °C based on thermogravimetric−differential thermogravimetric (TG−DTG) analysis. The photocatalytic activities of the as-prepared SQ/TiO 2 composites were assessed in terms of the degradation rate of methylene blue (MB) under visible-light irradiation. The ISQ/TiO 2 composites achieved best enhancement of photocatalytic activity under 150 min of visible-light irradiation. When ISQ/TiO 2 nanocomposites were applied for different photocatalytic degradation cycling times, the degradation rate still reached 68%, which reflects the fact that SQ/TiO 2 composites have a high photostability in the photocatalytic process. When taking the degradation rate and photoresponse into consideration, the combination mode between the ISQ dye and TiO 2 that obtained the optimal degradation rate tended to be a hydrogen bond, which exhibited a stronger binding force than the simple physical absorption of m-ISQ/TiO 2 and c-BSQ/TiO 2 based on the FT-IR analysis. Using total organic carbon (TOC) test and liquid chromatography (LC) results, we verified the degree of mineralization of the MB molecule. Based on the fluorescence spectra, the highest fluorescence quantum yield of ISQ dye (0.124) was far greater than those of c-BSQ (0.036) and m-ISQ (0.02). The molecular structures of the squaraine dyes and the electron distributions of their highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) states were given by geometrical optimization with Gaussian 98 at the B3LYP/6-311+G(d,p) level. Compared with the optical band gap calculated using the Tauc plot equation, we suggest that its energy was slightly less than the band gap due to the absorbed photon. This might be related to the localized central electronic, phonon, and local energy levels between the conduction band (CB) and the valence band (VB). The value of the optical band gap calculated from UV diffuse reflection spectroscopy (DRS) becomes less than the theoretical calculated energy band gap.

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A facile and highly efficient green synthesis of carbazole derivatives containing a six-membered ring

Cited by 9 publications

References 48 publications

Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong?

Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong?

Crystal structure of 9-butyl-6-[2-(pyridin-4-yl)ethenyl]carbazol-3-amine

Effect of Dye Structure on Optical Properties and Photocatalytic Behaviors of Squaraine-Sensitized TiO₂ Nanocomposites

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A facile and highly efficient green synthesis of carbazole derivatives containing a six-membered ring

Cited by 9 publications

References 48 publications

Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong?

Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong?

Crystal structure of 9-butyl-6-[2-(pyridin-4-yl)ethenyl]carbazol-3-amine

Effect of Dye Structure on Optical Properties and Photocatalytic Behaviors of Squaraine-Sensitized TiO2 Nanocomposites

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Effect of Dye Structure on Optical Properties and Photocatalytic Behaviors of Squaraine-Sensitized TiO₂ Nanocomposites