Design of Organic Structures in the Solid State: Molecular Tapes Based on the Network of Hydrogen Bonds Present in the Cyanuric Acid.cntdot.Melamine Complex

Zerkowski, Jonathan A.; MacDonald, John C.; Seto, Christopher T.; Wierda, Derk A.; Whitesides, George M.

doi:10.1021/ja00085a018

Cited by 199 publications

(130 citation statements)

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“…It was found that barbiturates or cyanurates could self-assemble into highly organized structures such as linear tapes, crinkle tapes, or rosettes with complementary hydrogen-bonding melamines in the solid state or solution. [10][11][12][13][14][15][16][17][18] More recently, the formation of hydrogenbonding networks between these complementary components has also been investigated in 2-D at the air-water interface. 19,20 Traditionally, it was believed that hydrogen bonding directed molecular recognition is difficult in polar media, such as water, due to the competition from the latter.…”

Section: Introductionmentioning

confidence: 99%

Polarization-Modulated Infrared Reflection Absorption Spectroscopic Studies of a Hydrogen-Bonding Network at the Air−Water Interface

et al. 1999

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The hydrogen-bonding network formed between a triaminotriazine amphiphile (2C 18 TAZ, 1) and complementary barbituric acid (BA, 2) at the air-water interface is investigated by polarization-modulated infrared reflection absorption spectroscopy (PM-IRRAS). The molecular structure and orientation of the 1:1 hydrogenbonding network at the air-water interface is revealed in this study. Without the addition of BA to the subphase, the NH 2 scissoring of 2C 18 TAZ appeared in the spectrum as a broad negative absorption band between 1660 and 1605 cm -1 , indicating its perpendicular orientation to the air-water interface. When BA was added to the subphase, the NH 2 scissoring absorption band from the triaminotriazine moiety disappeared due to the complementary hydrogen bonding of BA to the 2C 18 TAZ monolayer. The formation of the rigid 1:1 hydrogen-bonding network also resulted in the disappearance of one of the ring quadrant stretch absorption bands of the 2C 18 TAZ molecule. New bands which are attributed to the vibration of BA can be clearly seen. Particularly, the CdO stretch from BA shows up in the spectra as two negative absorption bands around 1700 cm -1 . The negative signature of these two bands suggests that the BA molecules are oriented in the hydrogen-bonding network with the C-2 carbonyl positioned vertically toward the air, and the C-4 and C-6 carbonyls directed into the water subphase. This is consistent with formation of an assembly which optimizes the use of complementary hydrogen bonding between two components. Furthermore, the effect of competitive polar organic solvents in subphase, such as DMSO, on the hydrogen-bonding network has also been observed in this study. Compared to the previous IRRAS studies on the similar monolayers, the sensitivity of PM-IRRAS is obviously improved. PM-IRRAS will likely become a powerful analytical technique for the characterization of molecular structure and orientation of Langmuir monolayers at the air-water interface.

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Section: Introductionmentioning

confidence: 99%

Polarization-Modulated Infrared Reflection Absorption Spectroscopic Studies of a Hydrogen-Bonding Network at the Air−Water Interface

et al. 1999

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“…[54] Two different assemblies can be formed depending on the relative orientation of the individual components, that is the cyclic hexameric rosette assembly 1 3´23 , [55] or tapelike assemblies [1´2] n , which can be subdivided into linear [56] and crinkled tapes ( Figure 2). [57] It has been suggested by Whitesides and co-workers that melamines with bulky substituents, such as 1 b (R tBuPh), exclusively form the cyclic rosette assembly 1 3´23 as a direct [a] Notation ª º means that assembly is stable at concentrations > 10 À2 m and ª ± º means that assembly is not stable in solution.…”

Section: Introductionmentioning

confidence: 99%

Ag+ Labeling: A Convenient New Tool for the Characterization of Hydrogen-Bonded Supramolecular Assemblies by MALDI-TOF Mass Spectrometry

et al. 2000

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Herein we describe our results on the characterization of a wide variety of different hydrogen-bonded assemblies by means of a novel matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS) technique with Ag+ labeling. The labeling technique with Ag+ ions is extremely mild and provides a nondestructive way to generate charged assemblies that can be detected by mass spectrometry. Up to now more than 25 different single (1(3).2(3)), double (3(3).2(6)), and tetrarosettes (4(3).2(12)) have been successfully characterized by the use of this method. The success of the method entirely depends on the presence of a suitable binding site for the Ag+ ion. A variety of functionalities has been identified that provide strong binding sites for Ag+, either acting in a cooperative way (pi-arene and pi-alkene donor functionalities) or individually (cyano and crown ether functionalities). The method works well for assemblies with molecular weights between 2,000 and 8,000 Da, and most likely far beyond this limit.

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“…[6] Hence, they were amply explored for self-assembly purposes in solution [7] and in three-dimensional crystals. [8] Noncovalent bonds also are attractive tools to control the surface ordering of molecules, polymers, [9] or nanoparticles, [4,5,10] provided the latter are dressed with suitable ligands. Immobilization of nanoparticles (NPs) in well-controlled 2D arrangements will facilitate their integration in future devices.…”

Section: Introductionmentioning

confidence: 99%

“…[24] In the only related example, Baron and co-workers immobilized CdS NPs, using derivatives of barbiturates and triaminodiazines, [25] moieties known to form extended H-bonded structures. [8] Here we present the selective surface-binding of Au 55 clusters, based on molecular recognition between ligands designed to yield pair-wise H-bonding interactions (rather than extended structures), as shown in Scheme 2. In addition to nanoparticle Using a complementary pair of simple alkylthiolates with hydrogen-bonding moieties, functionalized Au 55 clusters could be selectively deposited onto self-assembled monolayers on gold that carry the opposite functionality.…”

Section: Introductionmentioning

confidence: 99%

Selective Immobilization of Nanoparticles on Surfaces by Molecular Recognition using Simple Multiple H‐bonding Functionalities

Brom

Arfaoui

Cren

et al. 2007

Adv Funct Materials

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Using a complementary pair of simple alkylthiolates with hydrogen‐bonding moieties, functionalized Au55 clusters could be selectively deposited onto self‐assembled monolayers on gold that carry the opposite functionality. The deposition can be readily controlled by the medium in which the clusters are dissolved and by the density of the functionalities in the self‐assembled monolayers, and yields single clusters as well as two‐dimensional cluster assemblies on the surface. The clusters are sufficiently strongly bound to give structures that are stable at ambient temperature, and that allow scanning tunneling spectroscopy on single clusters on the surface.

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Design of Organic Structures in the Solid State: Molecular Tapes Based on the Network of Hydrogen Bonds Present in the Cyanuric Acid.cntdot.Melamine Complex

Cited by 199 publications

References 0 publications

Polarization-Modulated Infrared Reflection Absorption Spectroscopic Studies of a Hydrogen-Bonding Network at the Air−Water Interface

Polarization-Modulated Infrared Reflection Absorption Spectroscopic Studies of a Hydrogen-Bonding Network at the Air−Water Interface

Ag+ Labeling: A Convenient New Tool for the Characterization of Hydrogen-Bonded Supramolecular Assemblies by MALDI-TOF Mass Spectrometry

Selective Immobilization of Nanoparticles on Surfaces by Molecular Recognition using Simple Multiple H‐bonding Functionalities

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