Hydroxyl versus Carboxyl Substituent: Effects of Competitive and Cooperative Multiple Hydrogen Bonds on Concentration-Controlled Self-Assembly

Miao, Kai; Hu, Yi; Zha, Bao; Xu, Li; Miao, Xinrui; Deng, Wenli

doi:10.1021/acs.jpcc.6b03920

Cited by 42 publications

(40 citation statements)

References 47 publications

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“…A part of alkyl chains show good commensurability with the graphite surface and extend along one of the main symmetry axis in order to maximize the adsorbate−substrate interaction. Furthermore, hydrogen bonding interaction between the fluorenone cores is another kind of driving force, with the H atom in the π‐conjugated part exerts its role as the hydrogen bonds donor and O atom from the carbonyl group as the acceptor . The proposed structural models for the anti‐S‐like and S‐like patterns are shown in Figure c,d.…”

Section: Resultsmentioning

confidence: 99%

Exploration of Chirality and Achirality of Self‐Assembled Monolayer Formed by Unsymmetrically Substituted Fluorenone Derivative at the Liquid/Solid Interface

Miao

Dong

et al. 2017

Adv Materials Inter

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noncovalent forces, such as dipole-dipole interaction, [3] electrostatic interaction, [4] van der Waals interaction, [5] hydrogen bonds, [6] and π-π stacking. [7] Through physical adsorption, achiral molecules can self-assemble into chiral configurations on the achiral substrate due to the reduced freedom and constraint of the substrate lattice. [2d,8] Because of the rotation characteristics, porous networks show great potential in the process of chiral recognition and have received wide attentions. [9] However, nonporous networks also possess possibility of forming chiral polymorphs as long as the molecules are properly designed. Thus obtaining chirality via tiny structure modification will be a new attempt on fabricating chiral structures and will provide a new method on designing advanced functional materials in the field of surface science.Fluorenone derivatives have been reported to be used as liquid crystals. [10] Moreover, they were also good candidates for studying the self-assemblies at the liquid/highly oriented pyrolytic graphite (HOPG) interface, which have been widely explored in our group. We have previously reported that structural diversity was common to be observed and could be induced via changing the length of the alkyl chain, the concentration, and the solvent. For the bis-substituted fluorenone derivatives, molecules were arranged into a variety of nanopatterns which were regularly ordered but not chiral. [3,11] For the monosubstituted fluorenone derivatives, molecules adopted both chiral and achiral configurations and structural transition could be regulated between them. [12] Therefore, fabrication of chiral nanostructures using unsymmetrically substituted fluorenone derivatives seems to be a challenging but meaningful target. Fortunately, we realized this goal by efficient modification of the side chains.When the π-conjugated fluorenone core was substituted at the equal positions but substituted by unequal alkyl chains, chiral nanostructures were observed in its self-assembled monolayer on HOPG. The molecule we use in this study is 2-decyloxy-7-pentadecyloxy-9-fluorenone (DPF), as shown in Figure 1a. The first typical feature induced by the two different alkyl chains (C 10 H 21 and C 15 H 31 ) is that the long chains and the short chains are orderly interdigitated. As a result of this interdigitation, DPF molecules are usually notThe self-assemblies of 2-decyloxy-7-pentadecyloxy-9-fluorenone (DPF) are characterized by scanning tunneling microscopy at the liquid/solid interface. Achiral Dimer and chiral S-like structures are observed in 1-octanoic acid. The solvent molecule takes part in the self-assembly via forming COOH⋯OC and COOH⋯COOH hydrogen bonds. When 1-phenyloctane and n-tetradecane are used as the solvents, DPF self-assembles into chiral Z-like structure, which are classified into Types I-IV according to the packing styles. For the purpose of exploring the effect of solvent and the competition between these three structures, the self-assemblies of DPF in mixed solvents and ...

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Section: Resultsmentioning

confidence: 99%

Exploration of Chirality and Achirality of Self‐Assembled Monolayer Formed by Unsymmetrically Substituted Fluorenone Derivative at the Liquid/Solid Interface

Miao

Dong

et al. 2017

Adv Materials Inter

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“…For example, double hydrogen bonds (O-H•••O) are expected to appear between neighboring molecules possessing carboxylic groups. This strategy has been successfully used to stabilize the formation of porous and compact nanoarchitectures in a highly predictable fashion [35][36][37][38][39][40][41] . However, "push-pull" dyes usually have a complex structure with low symmetry.…”

Section: Introductionmentioning

confidence: 99%

Molecular trapping in two-dimensional chiral organic Kagomé nanoarchitectures composed of Baravelle spiral triangle enantiomers

et al. 2020

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The supramolecular self-assembly of a push-pull dye is investigated using scanning tunneling microscopy (STM) at the liquid-solid interface. The molecule has an indandione head, a bithiophene backbone and a triphenylamine-bithiophene moiety functionalized with two carboxylic acid groups as a tail. The STM images show that the molecules adopt an "L" shape on the surface and form chiral Baravelle spiral triangular trimers at low solution concentrations. The assembly of these triangular chiral trimers on the graphite surface results in the formation of two types of chiral Kagomé nanoarchitectures. The Kagomé-α structure is composed of only one trimer enantiomer, whereas the Kagomé-β structure results from the arrangement of two trimer enantiomers in a 1:1 ratio. These Kagomé lattices are stabilized by intermolecular O-H•••O hydrogen bonds between carboxylic acid groups. These observations reveal that the complex structure of the push-pull dye molecule leads to the formation of sophisticated two-dimensional chiral Kagomé nanoarchitectures. The subsequent deposition of coronene molecules leads to the disappearance of the Kagomé-β structure, whereas the Kagomé-α structure acts as the host template to trap the coronene molecules.

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“…Carboxylic groups have been grafted onto the triphenylamine group to promote intermolecular double hydrogen-bonds (O–H···O). This interaction has been successfully used to stabilize the formation of porous as well as compact nanoarchitectures on surfaces [ 41 , 42 , 43 , 44 , 45 , 46 , 47 ]. The compound-1 was synthesized according to the procedure described in ref.…”

Section: Methodsmentioning

confidence: 99%

Coronene and Phthalocyanine Trapping Efficiency of a Two-Dimensional Kagomé Host-Nanoarchitecture

et al. 2022

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The trapping of coronene and zinc phthalocyanine (ZnPc) molecules at low concentration by a two-dimensional self-assembled nanoarchitecture of a push–pull dye is investigated using scanning tunneling microscopy (STM) at the liquid–solid interface. The push–pull molecules adopt an L-shaped conformation and self-assemble on a graphite surface into a hydrogen-bonded Kagomé network with porous hexagonal cavities. This porous host-structure is used to trap coronene and ZnPc guest molecules. STM images reveal that only 11% of the Kagomé network cavities are filled with coronene molecules. In addition, these guest molecules are not locked in the host-network and are desorbing from the surface. In contrast, STM results reveal that the occupancy of the Kagomé cavities by ZnPc evolves linearly with time until 95% are occupied and that the host structure cavities are all occupied after few hours.

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Hydroxyl versus Carboxyl Substituent: Effects of Competitive and Cooperative Multiple Hydrogen Bonds on Concentration-Controlled Self-Assembly

Cited by 42 publications

References 47 publications

Exploration of Chirality and Achirality of Self‐Assembled Monolayer Formed by Unsymmetrically Substituted Fluorenone Derivative at the Liquid/Solid Interface

Exploration of Chirality and Achirality of Self‐Assembled Monolayer Formed by Unsymmetrically Substituted Fluorenone Derivative at the Liquid/Solid Interface

Molecular trapping in two-dimensional chiral organic Kagomé nanoarchitectures composed of Baravelle spiral triangle enantiomers

Coronene and Phthalocyanine Trapping Efficiency of a Two-Dimensional Kagomé Host-Nanoarchitecture

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