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Ivanov, A. V.; Lyakhov, S. A.; Yarkova, M. Yu.; Galatina, A. I.

doi:10.1023/a:1021686115034

Cited by 14 publications

(12 citation statements)

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“…37,[67][68][69][70][71][72][73][74] Lemieux and Ivanov have reported independently for non-charged liquid crystals 3-5 that a rigid uorenone core promotes formation of the SmC phase. [75][76][77][78][79][80] As mentioned above, in contrast to neutral calamitic liquid crystals ILCs are rather reluctant to form SmC phases. Despite the few known examples, [12][13][14][15][16][17][18] it is still an ongoing challenge to develop design principles for ILCs displaying both SmA and SmC phases.…”

Section: Introductionmentioning

confidence: 99%

Fluorenone imidazolium salts as novel de Vries materials

et al. 2020

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Section: Introductionmentioning

confidence: 99%

Fluorenone imidazolium salts as novel de Vries materials

et al. 2020

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“…Br-FC15, Cl-FC15, F-FC15, and H-FC15 molecules were synthesized as described in the reported literature. , 1-Phenyloctane (TCI, 99.9%) was used as received without further purification. The sample solutions were prepared by dissolving the compounds in 1-phenyloctane (concentration = 10 –6 –10 –4 M).…”

Section: Methodsmentioning

confidence: 99%

Halogen Substituent Effects on Concentration-Controlled Self-Assembly of Fluorenone Derivatives: Halogen Bond versus Hydrogen Bond

Dong

Miao

et al. 2019

J. Phys. Chem. C

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Self-assembled behaviors of three fluorenone derivatives substituted by different halogen atoms, 2-(pentadecyloxy)-6-bromo-fluorenone (Br-FC15), 2-(pentadecyloxy)-6-chloro-fluorenone (Cl-FC15), and 2-(pentadecyloxy)-6-fluoro-fluorenone (F-FC15), were investigated at the 1-phenyloctane/highly oriented pyrolytic graphite interface by scanning tunneling microscopy combined with density functional theory calculations in comparison with the self-assembly of 2-pentadecyloxy-fluorenone (H-FC15). It is found that different charge distributions on halogen substituents lead to a subtle change of the molecular packing nanostructures. By varying the solution concentrations, X-FC15 (X = Br, Cl, H) can self-assemble into polymorphic nanostructures, whereas only one pattern can be observed for the F-FC15 adlayer due to the stronger continuous C–H···F bonds. The intermolecular C–H···OC hydrogen bonds are the main driving forces for all the self-assembled patterns. Particularly, the halogen-based hydrogen bonds and the type-I X···X (X = Br, Cl) bonds act as the collaborative forces to stabilize the alternate adlayers. Furthermore, the halogen bonds (C–Br···OC and C–Cl···OC) make the crucial contribution to the distinct lamellar and the dumbbell-like patterns. The investigation suggests that the engineering of organic nanoarchitectures can be effectively tailored by the introduction of different halogen atoms.

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“…2,7-Bis(n-alkoxy)-9-fluorenone (F-OC n , n = 12 to 18) used in this study were synthesized as described in the literature. 27,28 F-OC n was obtained by repeated recrystallization in order to ensure the purity. n-Tetradecane and n-tridecane (TCI) were used as received.…”

Section: Methodsmentioning

confidence: 99%

Steric matching and the concentration induced self-assembled structural variety of 2,7-bis(n-alkoxy)-9-fluorenone at the aliphatic solvent/graphite interface

Miao

Cui

et al. 2014

Phys. Chem. Chem. Phys.

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Controlling and unraveling structural polymorphism has received special attention in 2D self-assembled monolayers. In this work, we investigated the steric matching and solution concentration controlled structural variety in the self-assembly of 2,7-bis(n-alkoxy)-9-fluorenone (F-OCn) at the n-tetradecane and n-tridecane/graphite interface under different concentrations, respectively. Scanning tunneling microscopy (STM) revealed that the coadsorbed adlayers of F-OCn and solvents (n = 12 to 16) were formed and exhibited concentration dependent 2D phases due to the steric matching. The self-assembled monolayer of F-OCn (n = 12 to 16) evolved from a low-density coadsorbed linear lamellar packing, which was formed at low concentrations, to higher-density patterns at relatively high concentrations. F-OC14 exhibited a complex structural variety, in which a systematic trend of decrease in the molecular density per unit cell with decreasing concentration was obtained. Except for F-OCn (n = 13, 15, 17), the zigzag structure showing the linear lamella with dimers was observed. Systematic experiments revealed that the self-assembly of F-OCn was chain-length dependent. The results provide insight into the structural variety exhibited by a series of organic molecules and furnish important guidelines to control the morphology by changing the solution concentration.

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Cited by 14 publications

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Fluorenone imidazolium salts as novel de Vries materials

Fluorenone imidazolium salts as novel de Vries materials

Halogen Substituent Effects on Concentration-Controlled Self-Assembly of Fluorenone Derivatives: Halogen Bond versus Hydrogen Bond

Steric matching and the concentration induced self-assembled structural variety of 2,7-bis(n-alkoxy)-9-fluorenone at the aliphatic solvent/graphite interface

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