Surface Tectonics of Nanoporous Networks of Melamine‐Capped Molecular Building Blocks formed through Interface Schiff‐Base Reactions

Liu, Xuan-He; Wang, Dong; Li, Wan

doi:10.1002/asia.201300546

Cited by 17 publications

(9 citation statements)

References 50 publications

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“…Voluminous information is available on the self-assembly of molecules driven by HB [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ]. HB interaction is responsible for the three-dimensional conformation of proteins, synthetic foldamers [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ], peptide catalysis, peptidomimetic design [ 34 , 35 , 36 , 37 , 38 , 39 ], double helical structure of DNA [ 40 , 41 ], unique properties of water [ 42 ], etc. Thus, in-depth knowledge of HB interaction aids in understanding the chemical properties of many organic and bio-macromolecules [ 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 ].…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations

Mishra

Suryaprakash

2017

Molecules

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The combined utility of many one and two dimensional NMR methodologies and DFT-based theoretical calculations have been exploited to detect the intramolecular hydrogen bond (HB) in number of different organic fluorine-containing derivatives of molecules, viz. benzanilides, hydrazides, imides, benzamides, and diphenyloxamides. The existence of two and three centered hydrogen bonds has been convincingly established in the investigated molecules. The NMR spectral parameters, viz., coupling mediated through hydrogen bond, one-bond NH scalar couplings, physical parameter dependent variation of chemical shifts of NH protons have paved the way for understanding the presence of hydrogen bond involving organic fluorine in all the investigated molecules. The experimental NMR findings are further corroborated by DFT-based theoretical calculations including NCI, QTAIM, MD simulations and NBO analysis. The monitoring of H/D exchange with NMR spectroscopy established the effect of intramolecular HB and the influence of electronegativity of various substituents on the chemical kinetics in the number of organic building blocks. The utility of DQ-SQ technique in determining the information about HB in various fluorine substituted molecules has been convincingly established.

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Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations

Mishra

Suryaprakash

2017

Molecules

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“…The use of melamine in Schiff base reaction restricted the advancement of the reaction to the formation of stoichiometric oligomers of finite size. 212,213 A similar effect was observed by using a nonplanar tetrahedral (sp 3 ) building-block. 214 Here it was suggested that the formation of supramolecular selfassemblies of these oligomers, stabilized by consequent intermolecular interactions, played a role in the limitation of the reaction advancement.…”

Section: Other Effectsmentioning

confidence: 99%

Controlling a Chemical Coupling Reaction on a Surface: Tools and Strategies for On-Surface Synthesis

2019

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On-surface synthesis is appearing as an extremely promising research field aimed at creating new organic materials. A large number of chemical reactions have been successfully demonstrated to take place directly on surfaces through unusual reaction mechanisms. In some cases the reaction conditions can be properly tuned to steer the formation of the reaction products. It is thus possible to control the initiation step of the reaction and its degree of advancement (the kinetics, the reaction yield); the nature of the reaction products (selectivity control, particularly in the case of competing processes); as well as the structure, position, and orientation of the covalent compounds, or the quality of the as-formed networks in terms of order and extension. The aim of our review is thus to provide an extensive description of all tools and strategies reported to date and to put them into perspective. We specifically define the different approaches available and group them into a few general categories. In the last part, we demonstrate the effective maturation of the on-surface synthesis field by reporting systems that are getting closer to application-relevant levels thanks to the use of advanced control strategies.

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“…STM is superior in visualizing two-dimensional patterns with atomic-level resolution in real space and revealing assembly mechanisms governing the two-dimensional crystalline processes. Meanwhile, the in situ morphologies of the two-dimensional structures could be captured without damaging or polluting the samples. , …”

Section: Introductionmentioning

confidence: 99%

“…Meanwhile, the in situ morphologies of the twodimensional structures could be captured without damaging or polluting the samples. 31,32 Related to the utility of noncovalent interactions to achieve well-ordered molecular self-assemblies, supramolecular liquid crystals are especially appealing. 33−35 Indeed, increased structural complexity and molecular order can be achieved in the bulk by the self-assembly of small building blocks, and this makes their preparation much easier than all-covalent methods.…”

Section: ■ Introductionmentioning

confidence: 99%

On-Surface Crystallization Behaviors of H-Bond Donor–Acceptor Complexes at Liquid/Solid Interfaces

Cheng

Xiao

et al. 2019

Langmuir

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Two-dimensional (2D) crystallization behaviors of A-TPC n (n = 4, 6, 10), T3C 4 , and hydrogen-bonded complexes T3C 4 @TPC n (n = 4, 6, 10) are investigated by means of scanning tunneling microscope (STM) observations and density functional theory (DFT) calculations. The STM observations reveal that A-TPC 4 , A-TPC 10 , and T3C 4 self-organize into dumbbell-shaped structures, well-ordered bright arrays, and zigzag structures, respectively. Interestingly, T3C 4 @TPC 10 fails to form the cage-ball structure, whereas T3C 4 @TPC 4 and T3C 4 @TPC 6 co-assemble into cage-ball structures with the same lattice parameters. The filling rates of the balls of these two kinds of cage-ball structures depend heavily on the deposition sequence. As a result, the filling rates of the cages in T3C 4 /A-TPC n (n = 4, 6) with deposition of T3C 4 anterior to A-TPC n are higher than those in A-TPC n /T3C 4 (n = 4, 6) with the opposite deposition sequence. Furthermore, lattice defects formed by T3C 4 coexist with the cage-ball structures. Moreover, the similar energy per unit area of lattice defects (−0.101 kcal mol −1 Å −2 ) and the two cage-ball networks (−0.194 and −0.208 kcal mol −1 Å −2 , respectively), illustrating the similar stabilities of lattice defects and cage-ball networks, demonstrates the rationality of lattice defects. Combining STM investigations and DFT calculations, this work could provide a useful approach to investigate the 2D crystallization mechanisms of supramolecular liquid crystals on surfaces.

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Surface Tectonics of Nanoporous Networks of Melamine‐Capped Molecular Building Blocks formed through Interface Schiff‐Base Reactions

Cited by 17 publications

References 50 publications

Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations

Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations

Controlling a Chemical Coupling Reaction on a Surface: Tools and Strategies for On-Surface Synthesis

On-Surface Crystallization Behaviors of H-Bond Donor–Acceptor Complexes at Liquid/Solid Interfaces

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