Porous molecular networks formed by the self-assembly of positively-charged trigonal building blocks at the liquid/solid interfaces

Tahara, Kazukuni; Abraham, Maria L.; Igawa, Kosuke; Katayama, Kazunori; Oppel, Iris M.; Tobe, Yoshito

doi:10.1039/c4cc01576b

Cited by 9 publications

(6 citation statements)

References 32 publications

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“…1 nm between a pair of alkyl chains attached to one edge of a DBA molecule, is crucial to the formation of the interdigitating motif of the alkyl chains to maximize van der Waals interactions with neighboring molecules. Similar trigonal building blocks are also shown to form honeycomb patterns via alkyl–alkyl interactions. − Densely packed linear patterns in which two alkyl chains of a DBA are exposed to the solution phase were observed under certain conditions. We elucidated favorable conditions for the formation of the porous 2D molecular networks with respect to the alkyl chain length, , kind of solvent, solute concentration, and temperature .…”

Section: Porous Network Formed By the Self-assembly Of Triangular Bui...mentioning

confidence: 96%

Host–Guest Chemistry in Integrated Porous Space Formed by Molecular Self-Assembly at Liquid–Solid Interfaces

et al. 2017

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Host-guest chemistry in two-dimensional (2D) space, that is, physisorbed monolayers of a single atom or a single molecular thickness on surfaces, has become a subject of intense current interest because of perspectives for various applications in molecular-scale electronics, selective sensors, and tailored catalysis. Scanning tunneling microscopy has been used as a powerful tool for the visualization of molecules in real space on a conducting substrate surface. For more than a decade, we have been investigating the self-assembly of a series of triangle-shaped phenylene-ethynylene macrocycles called dehydrobenzo[12]annulenes (DBAs). These molecules are substituted with six alkyl chains and are capable of forming hexagonal porous 2D molecular networks via van der Waals interactions between interdigitated alkyl chains at the interface of organic solvents and graphite. The dimension of the nanoporous space or nanowell formed by the self-assembly of DBAs can be controlled from 1.6 to 4.7 nm by simply changing the alkyl chain length from C to C. Single molecules as well as homoclusters and heteroclusters are capable of coadsorbing within the host matrix using shape- and size-complementarity principles. Moreover, on the basis of the versatility of the DBA molecules that allows chemical modification of the alkyl chain terminals, we were able to decorate the interior space of the nanoporous networks with functional groups such as azobenzenedicarboxylic acid for photoresponsive guest adsorption/desorption or fluoroalkanes and tetraethylene glycol groups for selective guest binding by electrostatic interactions and zinc-porphyrin units for complexation with a guest by charge-transfer interactions. In this Feature Article, we describe the general aspects of molecular self-assembly at liquid/solid interfaces, followed by the formation of programmed porous molecular networks using rationally designed molecular building blocks. We focus on our own work involving host-guest chemistry in integrated nanoporous space that is modified for specific purposes.

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Section: Porous Network Formed By the Self-assembly Of Triangular Bui...mentioning

confidence: 96%

Host–Guest Chemistry in Integrated Porous Space Formed by Molecular Self-Assembly at Liquid–Solid Interfaces

et al. 2017

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“…In addition to the utilization as ligand for metal binding, salicylaldehyde-derived TAG salts can also be used for the formation of two-dimensional, porous molecular networks by self-assembly on solid surfaces [12]. The introduction of a charged, trigonal core at solid surfaces results in additional bonding sites for other ions or molecules.…”

Section: Tag-based Ligandsmentioning

confidence: 99%

Triaminoguanidinium-Based Ligands in Supramolecular Chemistry

Eßen

Göb

Oppel

2015

Topics in Heterocyclic Chemistry

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This chapter will give an insight into the chemistry of triaminoguanidinium salts (TAGX), their synthesis, and potential application. The main focus will be on the utilization of triaminoguanidinium salts as building blocks for C 3 -symmetric ligand systems. Both the direct application and the coordination chemistry leading to molecular and supramolecular coordination compounds will be presented. The formation of basic coordination compounds and different discrete coordination cages will be described in more detail.

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“…1 H NMR titration (Figure S18 in the SI) showed the signals for the active protons shifted in certain degrees, the peak shapes broadened, and some new signals appeared, which indicated coordination of L with Cd 2+ . , Moreover, the 1:3 complex was also proved by 1 H NMR titration and ESI-MS of L−Cd 2+ (Figure S18 and S19 in the SI). Besides, the coordination mode of L –Zn 2+ was different from that of L –Cd 2+ (Figure S20 in the SI).…”

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confidence: 92%

A Highly Sensitive C₃-Symmetric Schiff-Base Fluorescent Probe for Cd²⁺

Jiang

et al. 2014

Inorg. Chem.

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A new C3-symmetric Schiff-base fluorescent probe (L) based on 8-hydroxy-2-methylquinoline has been developed. As expected, the probe L can display high fluorescent selectivity for Cd(2+) over Zn(2+) and most other common ions in neutral ethanol aqueous medium. Moreover, the mechanism of the L-Cd(2+) complex has been confirmed by X-ray crystallography and density functional theory calculation results. More importantly, L could be used to image Cd(2+) within living cells.

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Porous molecular networks formed by the self-assembly of positively-charged trigonal building blocks at the liquid/solid interfaces

Abstract: Tris-(2-hydroxybenzylidene)triaminoguanidinium salts having six alkyl chains with proper spacing served as new molecular building blocks for the formation of porous honeycomb networks by van der Waals interaction between interdigitated alkyl chains at the liquid/graphite interfaces.

Cited by 9 publications

References 32 publications

Host–Guest Chemistry in Integrated Porous Space Formed by Molecular Self-Assembly at Liquid–Solid Interfaces

Host–Guest Chemistry in Integrated Porous Space Formed by Molecular Self-Assembly at Liquid–Solid Interfaces

Triaminoguanidinium-Based Ligands in Supramolecular Chemistry

A Highly Sensitive C₃-Symmetric Schiff-Base Fluorescent Probe for Cd²⁺

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Porous molecular networks formed by the self-assembly of positively-charged trigonal building blocks at the liquid/solid interfaces

Abstract: Tris-(2-hydroxybenzylidene)triaminoguanidinium salts having six alkyl chains with proper spacing served as new molecular building blocks for the formation of porous honeycomb networks by van der Waals interaction between interdigitated alkyl chains at the liquid/graphite interfaces.

Cited by 9 publications

References 32 publications

Host–Guest Chemistry in Integrated Porous Space Formed by Molecular Self-Assembly at Liquid–Solid Interfaces

Host–Guest Chemistry in Integrated Porous Space Formed by Molecular Self-Assembly at Liquid–Solid Interfaces

Triaminoguanidinium-Based Ligands in Supramolecular Chemistry

A Highly Sensitive C3-Symmetric Schiff-Base Fluorescent Probe for Cd2+

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Product

Resources

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A Highly Sensitive C₃-Symmetric Schiff-Base Fluorescent Probe for Cd²⁺