Engineering porous and compact two-dimensional nanoarchitectures on surfaces taking advantage of bisterpyridine-derivatives self-assembly

Silly, Fabien; Kervella, Yann; Jousselme, Bruno

doi:10.1039/c5ra22117j

Cited by 10 publications

(11 citation statements)

References 48 publications

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“…2D molecular self-assembly at the solid–liquid interface has been widely investigated over the past few decades by scanning tunneling microscopy (STM) under ambient conditions. − The adlayers are stabilized by supramolecular interactions including van der Waals force, − hydrogen bond, − halogen bond, − and interfacial molecule–substrate interactions. The halogen bond is an important new weak noncovalent interaction in the engineering of 2D self-assembly.…”

Section: Introductionmentioning

confidence: 99%

Solvent Effect on Halogen-Bonded Self-Assembled Nanostructures of a 2,9-Dibromo-Phenanthridine Derivative at the Liquid–Solid Interface

Peng

Zeng

et al. 2021

J. Phys. Chem. C

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Probing the halogen-bonded nanostructures of two-dimensional (2D) supramolecular self-assembly is essential to understand and engineer the nature of halogen bonding. However, exploring the formation mechanism of the halogen bond still remains a challenge because it is a new weak noncovalent interaction. Herein, we introduce nitrogen atoms and Br groups in the conjugated core to synthesize 2,9-dibromo-6-(hexadecyloxy)phenanthridine (2,9-DHP) in order to fabricate multiple action sites of halogen bonds. We investigate the solvent effect on the 2D molecular self-assembly at the liquid–solid interface by using scanning tunneling microscopy. 1-Octanoic acid, n-tridecane, n-tetradecane, and n-hexadecane are chosen as the solvents. The coadsorption of 1-octanoic acid molecules at low concentrations by the molecule–solvent Br···O halogen bonds could change the molecular arrangement. n-Tridecane, n-tetradecane, and n-hexadecane also coadsorb in the adlayers; however, the molecular packing and intermolecular interactions of 2,9-DHP remain the same at different solution concentrations. The results demonstrate that the molecule–molecule N···Br···H halogen bonds are strong enough to overcome the transformation of intermolecular interactions.

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Section: Introductionmentioning

confidence: 99%

Solvent Effect on Halogen-Bonded Self-Assembled Nanostructures of a 2,9-Dibromo-Phenanthridine Derivative at the Liquid–Solid Interface

Peng

Zeng

et al. 2021

J. Phys. Chem. C

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Section: Introductionmentioning

confidence: 99%

“…Self-assembly of two-dimensional (2D) supramolecular structures driven by the formation of weak C–H···O, C–H···F, , and C–H···N − bonding and their combination with O–H···O bonds has been observed on solid surfaces. C–H···N interactions are known to occur between pyridine derivatives − and other nitrogen-containing molecular building blocks . C–H···F bonding arises as the primary intermolecular interaction stabilizing molecular networks of partially fluorinated porphyrin and phthalocyanine on solid substrates, but in other cases, it plays a complementary role in addition to stronger HB interactions …”

Section: Introductionmentioning

confidence: 99%

Modeling of High-Temperature Ordered Structures with Weak Intermolecular C–H···F and C–H···N Bonds

Ibenskas

Tornau

2021

J. Phys. Chem. C

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The self-assembly of a hydrogen bond “donor–acceptor” system with fluorinated pyridyl groups is considered to study the emergence of different ordered structures bonded by weak C–H···F and C–H···N bonds. We model the ordering of 4,4′-bis(2,6-difluoropyridin-4-yl)-1,1′-biphenyl (BDFPBP) as a typical example of this type of linear molecules. BDFPBP on Au(111) is known to assemble into four molecular arrangements: a herringbone phase at room temperature and three other structures at 450–460 K. In our model, we assume partial deprotonation of donor sites in phenyl and pyridyl rings during heating. Therefore, as representatives of the BDFPBP molecular system at higher temperatures, we choose seven types of molecules (one intact and six with differently damaged donor sites) and suggest the mechanisms of their bonding. Using density functional theory, we estimate the energies of different hydrogen-bonding motifs for intact and damaged molecules. We also perform Monte Carlo simulations for homo- and bimolecular ensembles to obtain all experimentally observed molecular phases. In addition, we reveal several new structures and their coexistences with the phases known from experiments.

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“…Inspired by these results and our previous work, we envisioned to investigate the molecular conformation and self-assembly of regioisomeric pyridyl-flanked DPP derivatives from molecular scale in order to identify the intra- and intermolecular interactions. In most cases, pyridine groups could adopt different orientation to stabilize hydrogen-bonded arrangements. − For example, Silly et al reported the terpyridine groups of bisterpyridine derivative adopted s- cis and s- trans as well as s- trans and s- trans conformations in the self-assembled layers …”

Section: Introductionmentioning

confidence: 99%

Effect of Pyridyl Orientation on the Molecular Conformation and Self-Assembled Morphology of Regioisomeric Diketopyrrolopyrrole Derivatives

et al. 2017

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We reported the synthesis, characterization, and selfassembly of two new regioisomeric π-conjugated chromophores (p-DBPy and d-DBPy) based on pyridyl-flanked diketopyrrolopyrrole (DPP), where the nitrogen atom in the pyridyl was proximal or distal to the central DPP unit. Their solid powders and solutions displayed different colors, especially for p-DBPy, which could be attributed to the conversion of molecular conformation and different intermolecular aggregations. UV−vis spectra demonstrated that the possible intermolecular hydrogen bonding existed in the solution of p-DBPy. Of particular interest is that the morphology of solid powders and thin films for each molecule investigated by SEM and AFM, respectively, were dramatically different owing to different intermolecular interactions and different crystal growth speed. Their spectroscopic and electrochemical properties turned out to be strongly dependent on the orientation of the pyridyl group. DFT calculations were performed to determine the optimized molecular conformation and molecular 3D charge density. At the liquid−solid interface, as visualized by STM, d-DBPy formed a 2D fishbone-like adlayer with linear molecular conformation by the molecule−substrate van der Waals force; however, p-DBPy self-assembled into a fish-scale-like pattern with flexed molecular conformation resulting from intra-and intermolecular hydrogen bonds. Compared with the 2D adlayers, the π−π stacking is another important driving force to determine the morphology of the films. The results demonstrated that understanding the effect of pyridyl orientation along the conjugated core on the molecular conformation and self-assembly is of critical importance for fabricating desired films with special morphology for high-performance organic electronic devices.

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Engineering porous and compact two-dimensional nanoarchitectures on surfaces taking advantage of bisterpyridine-derivatives self-assembly

Cited by 10 publications

References 48 publications

Solvent Effect on Halogen-Bonded Self-Assembled Nanostructures of a 2,9-Dibromo-Phenanthridine Derivative at the Liquid–Solid Interface

Solvent Effect on Halogen-Bonded Self-Assembled Nanostructures of a 2,9-Dibromo-Phenanthridine Derivative at the Liquid–Solid Interface

Modeling of High-Temperature Ordered Structures with Weak Intermolecular C–H···F and C–H···N Bonds

Effect of Pyridyl Orientation on the Molecular Conformation and Self-Assembled Morphology of Regioisomeric Diketopyrrolopyrrole Derivatives

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