Hydrogen bond‐Driven Self–Assembly between Amidinium Cations and Carboxylate Anions: A Combined Molecular Dynamics, NMR Spectroscopy, and Single Crystal X‐ray Diffraction Study

Thomas, Matthias; Lagones, Thomas Anglim; Judd, Martyna; Morshedi, Mahbod; O’Mara, Megan L.; White, Nicholas G.

doi:10.1002/asia.201700406

Cited by 36 publications

(34 citation statements)

References 54 publications

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“…[59] However, the organic salts constructed from tecton with carboxy group hardly exhibit permanent porosity due to its medium strength acid nature. [60][61][62][63][64][65][66][67] White and co-workers reported a supramolecular framework ([2•(TP) 2 ] n ) by using carboxylate (C 2 tecton) and amidinium (T d tecton) interaction (Figure 3a) in water at room temperature.…”

Section: Organic Acid Tecton With Carboxy Groupmentioning

confidence: 99%

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Crystalline Porous Organic Salts: From Micropore to Hierarchical Pores

et al. 2020

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fluids at the molecular level to achieve storage, separation, transformation and other functions and have aroused a wide range of interests from basic to applied research. [1,2] For instance, crystalline zeolitic materials with uniform and tuneable pore architecture have been widely utilized to facilitate various processes such as catalytic reactions, adsorption-separation, and ion-exchange. The advantageous features of zeolites include large surface areas and pore volume, tuneable porosity, controllable compositions, superior stability, and fine shape-selectivity of guest molecules. [3-6] Inspired by the success of zeolites, the development of hybrid porous materials (e.g., metal-organic frameworks (MOFs)), [7] organic porous materials (e.g., hyper crosslinked polymer (HCPs), [8,9] conjugated microporous polymers (CMPs), [10,11] polymers of intrinsic microporous (PIMs), [12] porous aromatic frameworks (PAFs), [13] covalent organic frameworks (COFs), [14,15] etc.) had a booming growth in last years, which greatly expanded the applications of porous materials with strengthened material functionality. Though recent advances of the abovementioned hybrid/organic porous materials provide some examples possessing high polar pores, [16-23] the synthesis of functional porous materials with the capability of adsorption, recognition and transport of high polar molecules is still highly challenging. In the history of porous materials, permanent porosity is an important criterion to distinguish porous materials from common network compounds composed of similar linkers and building units. [24-27] The permanent porosity refers to the voids of the framework compound after stripping guest molecules, which are permanently and reversibly accessible for alternative guest molecules. The permanent porosity of materials is usually verified by the widely used reversible gas adsorption method such as nitrogen or carbon dioxide adsorption. [27] Meanwhile, the obtained gas sorption isotherms can be applied to the determination of surface area and other porous characteristics using the different data treatment methods such as Brunauer-Emmett-Teller (BET), Dubinin-Astakhov (DA) methods and so on. In the case of large amount of crystalline frameworks constructed by organic salt bond, only those species contain such kind of permanent porosity can be referred to really "porous" or "open framework," i.e., CPOSs. As-synthesized crystalline organic salts (COSs) which contain guest molecules and have no accessible porosity due to the Crystalline porous organic salts (CPOSs), as an emerging class of porous organic materials, combining the uniform microporous system and distinct polarized channels, have become a highly evolving field of important current interest. The unique ionic bond of a CPOS endows the confined channels with high polarity, making CPOSs distinct from other organic frameworks. CPOSs show many fascinating properties, such as proton conductivity and fast transport of polar molecules, which involve the interaction between highly pola...

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Section: Organic Acid Tecton With Carboxy Groupmentioning

confidence: 99%

“…[ 59 ] However, the organic salts constructed from tecton with carboxy group hardly exhibit permanent porosity due to its medium strength acid nature. [ 60–67 ]…”

Section: Crystalline Porous Organic Saltsmentioning

confidence: 99%

Crystalline Porous Organic Salts: From Micropore to Hierarchical Pores

et al. 2020

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“…Especially, π‐conjugated CTFs have a strong absorption in the visible‐light region to effectively harvest solar light [65] . These materials have been emerged as promising photosensitizers for active hydrogen production under visible‐light irradiation, wherein Pt/Pd complexes or nanoparticles were used as water‐reduction catalysts (WRCs) [25,57–60,66–68] . To the best of our knowledge, heterogeneous photocatalytic systems combining non‐noble metal WRCs with CTFs have not been explored for hydrogen generation.…”

Section: Introductionmentioning

confidence: 99%

Boosting Visible‐Light‐Driven H₂ Evolution of Covalent Triazine Framework from Water by Modifying Ni(II) Pyrimidine‐2‐thiolate Cocatalyst

Cui

Guo

et al. 2020

ChemCatChem

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Covalent triazine frameworks (CTFs) have recently emerged as prospective photoactive materials coupled with Pt or Pd cocatalyst for the hydrogen evolution. Herein, we report visible‐light driven hydrogen generation catalyzed by heterogeneous systems combining CTF photosensitizers and a noble‐metal‐free cocatalyst for the first time. CTF‐HC2 was doped with two‐dimensional Ni(II) pyrimidine‐2‐thiolate ([Ni(pymt)2]n) to yield a series of x‐[Ni(pymt)2]n/CTF‐HC2 (x=3, 6, 9, 12, 15, 18 and 24 wt %) composites. Illuminated with λ>420 nm, [Ni(pymt)2]n/CTF‐HC2 materials display excellent photocatalytic performance for H2 generation from water. The highest hydrogen evolution rate is up to 3472 μmol h−1 g−1, which is 68 times of bare CTF‐HC2 (51 μmol h−1 g−1) and 1.16 times of CTF‐HC2 doped 2.0 wt % Pt (2991 μmol h−1 g−1). The efficient and recyclable heterogeneous photocatalytic H2 production from water under visible light has been established.

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“…(8) hydrogen bonding geometries 32 (Figure 1), although other hydrogen bond geometries have also been observed for amidinium•••carboxylate interactions. [30][31][33][34][35] Pentiptycenes, part of the larger family of iptycenes, 36,37 are rigid molecules with phenyl rings attached to two [2.2.2]bicyclooctatriene bridgehead systems. The rigidity and geometry of pentiptycenes prevents them from packing efficiently, and this property has been used to prepare porous organic polymers, [38][39][40][41][42] and metal organic frameworks.…”

Section: Introductionmentioning

confidence: 99%

Open Pentiptycene Networks Assembled through Charge-Assisted Hydrogen Bonds

Boer

Wang

MacLachlan

et al. 2019

Crystal Growth & Design

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A series of hydrogen bonded networks was prepared incorporating ditopic, tritopic or tetratopic poly-amidinium tectons and linear pentiptycene dicarboxylates. The ditopic amidinium forms a 1D hydrogen bonded chain when combined with the pentiptycene tecton while the tritopic trigonal planar amidinium tecton forms a 2D honeycomb network. A tetratopic amidinium tecton forms a 3D diamondoid network which is 32-fold interpenetrated, the joint-highest degree of interpenetration observed for a hydrogen bonded network. The bulky pentiptycene functionality prohibits the polymers from packing efficiently, leading to voids within each structure. These frameworks were envisaged as potential molecular motors, but unfortunately a lack of stability to solvent removal precluded an investigation of these properties.

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Hydrogen bond‐Driven Self–Assembly between Amidinium Cations and Carboxylate Anions: A Combined Molecular Dynamics, NMR Spectroscopy, and Single Crystal X‐ray Diffraction Study

Cited by 36 publications

References 54 publications

Crystalline Porous Organic Salts: From Micropore to Hierarchical Pores

Crystalline Porous Organic Salts: From Micropore to Hierarchical Pores

Boosting Visible‐Light‐Driven H₂ Evolution of Covalent Triazine Framework from Water by Modifying Ni(II) Pyrimidine‐2‐thiolate Cocatalyst

Open Pentiptycene Networks Assembled through Charge-Assisted Hydrogen Bonds

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Hydrogen bond‐Driven Self–Assembly between Amidinium Cations and Carboxylate Anions: A Combined Molecular Dynamics, NMR Spectroscopy, and Single Crystal X‐ray Diffraction Study

Cited by 36 publications

References 54 publications

Crystalline Porous Organic Salts: From Micropore to Hierarchical Pores

Crystalline Porous Organic Salts: From Micropore to Hierarchical Pores

Boosting Visible‐Light‐Driven H2 Evolution of Covalent Triazine Framework from Water by Modifying Ni(II) Pyrimidine‐2‐thiolate Cocatalyst

Open Pentiptycene Networks Assembled through Charge-Assisted Hydrogen Bonds

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Boosting Visible‐Light‐Driven H₂ Evolution of Covalent Triazine Framework from Water by Modifying Ni(II) Pyrimidine‐2‐thiolate Cocatalyst