A reinvestigation of the reaction of indole with 1,4-quinones

Prasad, Kanika

doi:10.1016/s0040-4039(01)82489-8

Cited by 13 publications

(8 citation statements)

References 3 publications

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“…1c, d). Although the individual reaction scheme was reported for synthesis of dye molecules from naphthoquinone (NQ) and Py derivatives 39,40 , the successive reactions were inhibited by protecting groups on the quinone and Py rings.…”

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confidence: 99%

Amorphous 2D materials containing a conjugated-polymer network

et al. 2019

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Two-dimensional materials, such as layered compounds and nanosheets, have attracted interest for their characteristic structures and properties. If layered materials containing functional organic molecules are synthesized, designed nanosheets can be obtained by exfoliation. Here we show the design and synthesis of an amorphous organic layered material containing a conjugated-polymer network, its exfoliation into nanosheets, and their applications. Copolymerization of benzoquinone and pyrrole generates random stacks of the conjugated polymer layers through successive CC bond formation and pericyclic reaction under mild conditions at 60°C. The amorphous organic layered materials are efficiently exfoliated into nanosheets in 44.6% after 1 h. The nanosheets are used as a metal-free electrocatalyst for hydrogen evolution reaction with the overpotential 0.28 V (vs. RHE). The present approach may be applied to the design of functional nanosheets with graphenelike structures under mild conditions.

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confidence: 99%

Amorphous 2D materials containing a conjugated-polymer network

et al. 2019

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“…The reaction between NQ and Py generated a macromolecule with condensed rings (Supplementary Figure S2 in the Supplementary Information). 42 In contrast, a similar segregated composite containing tetramethyl-1,4-benzoquinone crystals approximately 5 μm in size was obtained using the same method (Scheme 1 and Supplementary Figure S3 in the Supplementary Information). The results imply that the higher symmetry of the molecular structure provides larger, faceted crystals.…”

Section: Resultsmentioning

confidence: 99%

Phase separation of composite materials through simultaneous polymerization and crystallization

2017

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Composite materials have attracted much interest because of the emergent properties originating from the components. A variety of methods have been studied to control the morphology of composites based on noncrystalline polymers and crystalline materials. However, it is not easy to control complex morphologies, such as segregated sea-island structures, on the submicrometer scale. Polymerization induces crystallization, because supersaturation, which is required for crystallization, is achieved by the consumption of the monomer. Here we report a phase-separation approach based on simultaneous polymerization and crystallization as a new method for the morphological control of composite materials. Segregated polymer and organic crystal domains are obtained by polymerization of an organic monomer solution accompanied by simultaneous crystallization. The phase separation induced the generation of composite materials consisting of a redox-active quinone crystal and conductive polymer with a segregated structure on the submicrometer scale. The segregated composite of 2,3-dichloro-1,4-naphthoquinone and polypyrrole showed enhanced charge-storage properties based on the smooth redox reaction. The present phase-separation approach can be applied to a variety of functional segregated composite materials consisting of crystalline and polymer materials.

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“…This higher doping rate is ascribed to the direct bond formation between quinone and Py rings. 55 The conductivity was 4.9 and 3.9 S cm −1 for the pelletized samples of PPy nanosheets derived from TCBQ and TBBQ for 24 h by four-probe method, respectively (Table 1). As a reference, the pelletized sample of a commercial PPy microfiber showed 5.8 S cm −1 .…”

Section: Acs Applied Nano Materialsmentioning

confidence: 99%

Two-Dimensional Conductive and Redox-Active Nanostructures Synthesized by Crystal-Controlled Polymerization for Electrochemical Applications

Sato

Imai

Oaki

2018

ACS Appl. Nano Mater.

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Two-dimensional nanomaterials have attracted much interest for their anisotropic structures and emergent properties. Whereas a variety of inorganic nanosheets are prepared by exfoliation, design and synthetic strategies of organic nanosheets are still developing. Here we report on crystalcontrolled synthesis of conductive and redox-active organic polymer nanosheets with tunable thickness and lateral size. Although the nanosheets consist of classical conductive polymers, such as polypyrrole (PPy) and poly(3,4-ethylenedioxythiophene) (PEDOT), a new crystal-controlled polymerization approach provides 2D nanomaterials with enhanced and characteristic properties. Oxidative polymerization proceeds on the crystal surface of organic oxidants, such as quinone derivatives, with diffusion of the monomer vapor at low temperature under ambient pressure. The present method affords the control of lateral size and thickness of the nanosheets. The resultant nanosheets show the characteristic and enhanced properties originating from a 2D nature, such as the high structure anisotropy with aspect ratio around 10 4 , enhanced conductivity 287 S cm −1 , and specific charge−discharge capacitance 523 F g −1 at the current density of 18 A g −1 . The organic nanosheets with conductivity and redox activity can be used as a building block for development of functional materials and devices.

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A reinvestigation of the reaction of indole with 1,4-quinones

Cited by 13 publications

References 3 publications

Amorphous 2D materials containing a conjugated-polymer network

Amorphous 2D materials containing a conjugated-polymer network

Phase separation of composite materials through simultaneous polymerization and crystallization

Two-Dimensional Conductive and Redox-Active Nanostructures Synthesized by Crystal-Controlled Polymerization for Electrochemical Applications

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