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Microtubular Self-Assembly of Covalent Organic Frameworks.

ABSTRACT: Despite significant progress in the synthesis of covalent organic frameworks (COFs), reports on the precise construction of template-free nano- and microstructures of such materials have been rare. In the quest for dye-containing porous materials, a novel conjugated framework DPP-TAPP-COF with an enhanced absorption capability up to ?=800?nm has been synthesized by utilizing reversible imine condensations between 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (TAPP) and a diketopyrrolopyrrole (DPP) dialdehyde derivative. Surprisingly, the obtained COF exhibited spontaneous aggregation into hollow microtubular assemblies with outer and inner tube diameters of around 300 and 90?nm, respectively. A detailed mechanistic investigation revealed the time-dependent transformation of initial sheet-like agglomerates into the tubular microstructures.

SUBMITTER: Gole B

PROVIDER: S-EPMC6519380 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Microtubular Self-Assembly of Covalent Organic Frameworks.

Gole Bappaditya B Stepanenko Vladimir V Rager Sabrina S Grüne Matthias M Medina Dana D DD Bein Thomas T Würthner Frank F Beuerle Florian F

Angewandte Chemie (International ed. in English) 20171213 3

Despite significant progress in the synthesis of covalent organic frameworks (COFs), reports on the precise construction of template-free nano- and microstructures of such materials have been rare. In the quest for dye-containing porous materials, a novel conjugated framework DPP-TAPP-COF with an enhanced absorption capability up to λ=800 nm has been synthesized by utilizing reversible imine condensations between 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (TAPP) and a diketopyrrolopyrrole (DPP) ...[more]

PMID: 29072828

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Project description:Covalent organic frameworks (COFs) define a versatile structural paradigm combining attractive properties such as crystallinity, porosity, and chemical and structural modularity which are valuable for various applications. For the incorporation of COFs into optoelectronic devices, efficient charge carrier transport and intrinsic conductivity are often essential. Here, we report the synthesis of two imine-linked two-dimensional COFs, WTA and WBDT, featuring a redox-active Wurster-type motif based on the twisted tetragonal N,N,N',N'-tetraphenyl-1,4-phenylenediamine node. By condensing this unit with either terephthalaldehyde (TA) or benzodithiophene dialdehyde (BDT), COFs featuring a dual-pore kagome-type structure were obtained as highly crystalline materials with large specific surface areas and mesoporosity. In addition, the experimentally determined high conduction band energies of both COFs render them suitable candidates for oxidative doping. The incorporation of a benzodithiophene linear building block into the COF allows for high intrinsic macroscopic conductivity. Both anisotropic and average isotropic electrical conductivities were determined with van der Pauw measurements using oriented films and pressed pellets, respectively. Furthermore, the impact of different dopants such as F4TCNQ, antimony pentachloride and iodine on the conductivities of the resulting doped COFs was studied. By using the strong organic acceptor F4TCNQ, a massive increase of the radical cation density (up to 0.5 radicals per unit cell) and long-term stable electrical conductivity as high as 3.67 S m-1 were achieved for the anisotropic transport in an oriented film, one of the highest for any doped COF to date. Interestingly, no significant differences between isotropic and anisotropic charge transport were found in films and pressed pellets. This work expands the list of possible building nodes for electrically conducting COFs from planar systems to twisted geometries. The achievement of high and stable electrical conductivity paves the way for possible applications of new COFs in organic (opto)electronics.

Dataset Information

Microtubular Self-Assembly of Covalent Organic Frameworks.

Publications

Microtubular Self-Assembly of Covalent Organic Frameworks.

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