Synthesis of One‐Dimensional Schiff Base Polymers that Contain an Oligothiophene Building Block on the Graphite Surface

Sun, Xiaomeng; Fan, Lixia; Yang, Yongjing; Guo, Zongxia; Lei, Shengbin

doi:10.1002/chem.201406287

Cited by 6 publications

(5 citation statements)

References 102 publications

(134 reference statements)

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“…Further reducing the monomer concentration does not preclude the coexistence of irregular networks and HHTP islands (C ABBA = 1.65 10 À5 mol L À1 , C HHTP = 1.10 10 À5 mol L À1 ,F igure S6, Supporting Information), but only leads to lower surface coverage of the assembly.T hus, the results indicatet hat the strong adsorption and assembling properties of HHTP have as ignificant influence on the on-surfaceb oronic esterification reaction. [34,35] Hence, we propose that the formationo fw ell-ordered surfaceC OFs at the liquid/solidi nterface is ar esult of ad elicate balance of reactiond ynamics of covalentb ond formationa nd noncovalenta ssembling, both of which are influenced by surfaced iffusion of monomers, the intermolecular interaction between monomers and oligomers, and the molecule-substrate interaction. Fort he current system,s ince the HHTP monomer can form as upramolecular assembly with very high stability, it competes with the on-surface condensation.…”

Section: Structural Evolution For the On-surface Condensationmentioning

confidence: 98%

Room‐Temperature Synthesis of Covalent Organic Frameworks with a Boronic Ester Linkage at the Liquid/Solid Interface

Liu

Zhang

et al. 2016

Chemistry A European J

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With various prospected applications in the field of nanoelectronics and catalysis, on-surface synthesis of single-layer covalent organic frameworks (surface COFs) with designable structures and properties have attracted enormous interest. Herein, we report on a scanning tunneling microscopic investigation of the surface-confined synthesis of a covalently bonded boronic ester network directly at the octanoic acid/ highly oriented pyrolytic graphite(HOPG) interface under room temperature. The dynamic reaction process was investigated in detail. STM results indicate that the surface networks undergo structural evolution from a hybrid covalent/noncovalent multiwall porous network to single-wall hexagonal COF with the decrease of monomer concentration. Further experimental observation disclosed that the boronic ester-linked system is sensitive to instantaneous voltage pulses and the stimulation of the STM tip. In addition, the H NMR spectra has further confirmed that the surface and octanoic acid may play important roles in promoting the reaction between 4,4'-phenylazobenzoyl diboronic acid (ABBA) and 2,3,6,7,10,11-hexahydroxytriphenylene (HHTP) building units.

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Section: Structural Evolution For the On-surface Condensationmentioning

confidence: 98%

Room‐Temperature Synthesis of Covalent Organic Frameworks with a Boronic Ester Linkage at the Liquid/Solid Interface

Liu

Zhang

et al. 2016

Chemistry A European J

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“…Radical addition UHV 1D Heat Cu(1 1 0) [119,120] Boronic acid condensation (BAC) UHV 2D Heat Ag(1 1 1) [121] STM-tip Ag(1 0 0) [122] e − -beam Ag(1 0 0) [122] Ambient 2D Heat HOPG [123][124][125][126][127] BAC + Ullmann coupling UHV 2D Heat Au(1 1 1) [128] Carbonyl-analogue addition UHV 1D Heat Au(1 1 1) [129,130] 2D -Au(1 1 1) [131] Ag(1 1 1) [131] NaCl/Ag(1 0 0) [131] Schiff-base coupling UHV 0D Heat Au(1 1 1) [132,133] Solution 0D -Silicon in toluene [134] HOPG in 1-phenyloctane [135] 1D -HOPG in tetrahydrofuran [136] Au/mica in dimethylformamide [137] Heat HOPG in octanoic acid [138,139] pH [136,144] HOPG in octanoic acid [145] Graphene/Cu in octanoic acid [146] Heat HOPG in DMSO [147] HOPG in dimethylacetamide [148] HOPG in tetrahydrofuran [149] pH…”

Section: Reaction Condition Dimensions Stimulus Surface and Referencementioning

confidence: 99%

“…Short disordered oligomers have been obtained in the copresence of melamine islands at the solid-liquid interface between Au(1 1 1) and dimethylformamide by mixing melamine and terephthalaldehyde, with the melamine islands disappearing over time (approximately in 48 h) [137]. On the other hand, a certain degree of ordering of longer oligomeric structures has been achieved on HOPG [138,139].…”

Section: Schiff-base Couplingmentioning

confidence: 99%

“…A similar approach, depositing the precursor molecules in a tetrahydrofuran solution on HOPG, has been successfully adopted to form 1D and 2D polymers with different shape by changing the amines and aldehydes used as reactants, as shown inFigure 8c[136].Short disordered oligomers have been obtained in the co-presence of melamine islands at the solidliquid interface between Au(111) and dimethylformamide by mixing melamine and terephthalaldehyde, with the melamine islands disappearing over time (approximately in 48 hours)[137]. On the other hand, a certain degree of ordering of longer oligomeric structures has been achieved on HOPG[138][139].…”

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Reversibility and intermediate steps as key tools for the growth of extended ordered polymers via on-surface synthesis

Giovannantonio

Contini

2018

J. Phys.: Condens. Matter

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Surface-confined polymerization is a bottom-up strategy to create one- and two-dimensional covalent organic nanostructures with a π-conjugated backbone, which are suitable to be employed in real-life electronic devices, due to their high mechanical resistance and electronic charge transport efficiency. This strategy makes it possible to change the properties of the final nanostructures by a careful choice of the monomer architecture (i.e. of its constituent atoms and their spatial arrangement). Several chemical reactions have been proven to form low-dimensional polymers on surfaces, exploiting a variety of precursors in combination with metal (e.g. Cu, Ag, Au) and insulating (e.g. NaCl, CaCO) surfaces. One of the main challenges of such an approach is to obtain nanostructures with long-range order, to boost the conductance performances of these materials. Most of the exploited chemical reactions use irreversible coupling between the monomers and, as a consequence, the resulting structures often suffer from poor order and high defect density. This review focuses on the state-of-the-art surface-confined polymerization reactions, with particular attention paid to reversible coupling pathways and irreversible processes including intermediate states, which are key aspects to control to increase the order of the final nanostructure.

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“…Various hydrophobic polyimines have been prepared by condensation of polyaldehydes with polyamines . Obtained polyimines exhibited high stability against hydrolysis.…”

Section: Introductionmentioning

confidence: 99%

Controlling Release Kinetics of Payloads from Polymer Conjugates by Hydrophobicity

Seidi

Couffon

Prawatborisut

et al. 2019

Macro Chemistry & Physics

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Polymers conjugated with active molecules are useful for controlled delivery of corrosion inhibitors, phytosanitary products, and drugs. To avoid detrimental side effects, active molecules need to be selectively released upon specific external stimuli. Imine groups are highly acid‐labile linkages that are usually hydrolyzed in a few hours even in neutral medium, which can be detrimental when slow release of payloads is needed. Herein, release kinetics are adjusted by controlling hydrophobicity of pH‐responsive polymers. 5‐(Aminomethyl)‐8‐hydroxyquinoline (AM8HQ), an effective corrosion inhibitor, is conjugated via imine linkage to aldehyde pendant groups in three different copolymers. Release kinetics of AM8HQ from polymer nanoparticles are investigated in acidic and neutral media. Very fast release from polymethacrylate‐based and slow release from polystyrene‐based polymer conjugates clearly show that adjusting the hydrophobicity of the polymer backbone is an effective synthetic strategy to control the cleavage rate of highly labile imine bonds.

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Synthesis of One‐Dimensional Schiff Base Polymers that Contain an Oligothiophene Building Block on the Graphite Surface

Cited by 6 publications

References 102 publications

Room‐Temperature Synthesis of Covalent Organic Frameworks with a Boronic Ester Linkage at the Liquid/Solid Interface

Room‐Temperature Synthesis of Covalent Organic Frameworks with a Boronic Ester Linkage at the Liquid/Solid Interface

Reversibility and intermediate steps as key tools for the growth of extended ordered polymers via on-surface synthesis

Controlling Release Kinetics of Payloads from Polymer Conjugates by Hydrophobicity

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