Toward a Single-Layer Two-Dimensional Honeycomb Supramolecular Organic Framework in Water

Zhang, Kang‐Da; Tian, Jia; Hanifi, David; Zhang, Yuebiao; Sue, Andrew C.‐H.; Zhou, Tian; Zhang, Lei; Zhao, Xin; Liu, Yi; Li, Zhan‐Ting

doi:10.1021/ja4086935

Cited by 373 publications

(327 citation statements)

References 67 publications

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“…Specifically, organic 2D nanomaterials hold promise as biocompatible materials that can be chemically tailored and built from the bottom up, through the self-assembly of small molecule, protein, or polymer building blocks (2)(3)(4)(5). Polymer-based 2D nanomaterials, in particular, hold promise as templates for bottom-up assembly of circuits, semiconductors, and organicinorganic composite materials (6)(7)(8) as well as high surface area membranes for filtration, catalysis, and sensing (9,10).…”

mentioning

confidence: 99%

Assembly and molecular order of two-dimensional peptoid nanosheets through the oil–water interface

Robertson

Olivier

Qian

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

100

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Significance Peptoid nanosheets are an emerging class of 2D nanomaterials that have the potential for use in a variety of applications ranging from molecular sensors to artificial enzymes. Because peptoids are highly designable polymers, nanosheets provide a general platform on which to display an enormous diversity of functionalities. Nanosheets are known to form through a unique monolayer compression mechanism, catalyzed by the air–water interface. Here we demonstrate that nanosheets can be formed via adsorption of peptoids at an oil–water interface. Using vibrational sum frequency spectroscopy, we show that electrostatic interactions are essential in the formation of an ordered peptoid monolayer at the interface, a critical intermediate in the nanosheet assembly pathway. These findings open the door for enhancing the complexity and functionality of 2D nanomaterials.

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mentioning

confidence: 99%

Assembly and molecular order of two-dimensional peptoid nanosheets through the oil–water interface

Robertson

Olivier

Qian

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

100

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Section: Gobinda Dasmentioning

confidence: 99%

“…To address this issue, we have begun to develop charged COPs that incorporate redox-active viologens and are capable of adsorbing iodine vapor, toxic dyes, and metal ions by anion exchange. [22,23] Despite their great potential, viologen-based COPs are still rarely documented in the literature, though Li et al [24] have reported supramolecular organic frameworks (SOFs) that contain viologen struts and form in water.Herein, we report a one-pot, template-free solvothermal synthesis involving the Zincke reaction (Scheme 1) of two porous, viologen-linked COPs that contain pyrene derivatives as central core moieties. Both polymers exhibit outstanding chemical stability in common organic solvents, neutral water, and aqueous acid or base.…”

mentioning

confidence: 99%

Morphological Diversity in Nanoporous Covalent Organic Materials Derived from Viologen and Pyrene

Das¹,

Škorjanc²,

Sharma

et al. 2017

ChemNanoMat

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Adjustment of the morphology of covalent organic nanomaterials is a challenge but can be achieved by perturbing the planarity of the monomers used as core moieties in these polymers. Here we describe a templatefree Zincke reaction for the synthesis of covalent organic nanosheets (CONs) that stack several layers thick and of covalent organic tubes (COTs). Both materials contain the same viologen linker but different pyrene-based cores. Both polymeric materials are nanoporous, cationic, and highly stable in water, even in the presence of acid (1 M HCl) or base (1 M NaOH). Their porosity and ionic surfaces are responsible for high affinities and adsorption capacities for iodine vapor.Porous covalent organic polymers (COPs) are well known for their diverse applications in fields such as gas storage and separation, [1][2][3][4] catalysis, [5][6][7][8] sensing, [9,10] drug delivery, [11] and environmental remediation. [12] In order to design COPs with improved functionality, considerable research has been undertaken to understand the relationship between the morphologies and properties of these materials. [13][14][15] It has been observed that the morphology of COPs can be tuned by changing the symmetry of their constituent building blocks, but precise regulation of COP nanostructure remains a challenging task.Syntheses of covalent organic hollow tubes (COTs) and nanosheets (CONs) are of interest because their large surface areas facilitate the adsorption of small molecule guests. Porous, template-free COPs with uniform tube morphology have been used for device manufacturing [16] and catalysis, [17,18] but reports of the synthesis and application of this type of material remain scarce. Studies of covalent nanosheets are more prevalent, but, this type of material is obtained by either liquid phase exfoliation [19] or mechanical delamination, [20] and these two methods often result in low surface areas because the mechanical forces involved often cause pore blockage. In short, syntheses that rely on mechanical techniques for isolating nanosheets tend to be expensive and non-scalable and produce materials that have limited adsorption efficiency. Designing an efficient and green approach to the large-scale synthesis of porous CONs stacked several (or fewer) layers thick is an open challenge. [21] In general, porous COPs are synthesized from neutral building blocks, which limits the range of application for the materials. For example, neutral COPs are not optimal for the uptake of charged species, including toxic ionic guest molecules. To address this issue, we have begun to develop charged COPs that incorporate redox-active viologens and are capable of adsorbing iodine vapor, toxic dyes, and metal ions by anion exchange. [22,23] Despite their great potential, viologen-based COPs are still rarely documented in the literature, though Li et al. [24] have reported supramolecular organic frameworks (SOFs) that contain viologen struts and form in water.Herein, we report a one-pot, template-free solvothermal synthesis ...

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“…b) Self‐assembly of different building blocks with cucurbit[8]uril in water 35c. Reproduced from Refs.…”

Section: Porous Polyelectrolyte Membranesmentioning

confidence: 99%

Porous Polyelectrolytes: The Interplay of Charge and Pores for New Functionalities

2018

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The past decade has witnessed rapid advances in porous polyelectrolytes and there is tremendous interest in their synthesis as well as their applications in environmental, energy, biomedicine, and catalysis technologies. Research on porous polyelectrolytes is motivated by the flexible choice of functional organic groups and processing technologies as well as the synergy of the charge and pores spanning length scales from individual polyelectrolyte backbones to their nano‐/micro‐superstructures. This Review surveys recent progress in porous polyelectrolytes including membranes, particles, scaffolds, and high surface area powders/resins as well as their derivatives. The focus is the interplay between surface chemistry, Columbic interaction, and pore confinement that defines new chemistry and physics in such materials for applications in energy conversion, molecular separation, water purification, sensing/actuation, catalysis, tissue engineering, and nanomedicine.

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Toward a Single-Layer Two-Dimensional Honeycomb Supramolecular Organic Framework in Water

Cited by 373 publications

References 67 publications

Assembly and molecular order of two-dimensional peptoid nanosheets through the oil–water interface

Assembly and molecular order of two-dimensional peptoid nanosheets through the oil–water interface

Morphological Diversity in Nanoporous Covalent Organic Materials Derived from Viologen and Pyrene

Porous Polyelectrolytes: The Interplay of Charge and Pores for New Functionalities

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