Synthesis and 2D self-assembly at the liquid-solid interface of end-substituted star-shaped oligophenylenes

Rajwar, Deepa; Sun, Xiaoduan; Cho, Sung Ju; Grimsdale, Andrew C.; Fichou, Denis

doi:10.1039/c2ce25530h

Cited by 23 publications

(24 citation statements)

References 46 publications

(48 reference statements)

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“…The organic phase was eluted with THF and hexane through a silica column, then dried to yield a light yellow powder of TABPB (0.52 g, 60%; ref. 46). 1H NMR (400 MHz, DMSO- 3,448, 3,356, 3,205, 3,028, 1,616, 1,589, 1,497, 1,446, 1,389, 1,277, 1,180, 1,118, 810, 694, 571, 536, 505 cm À 1 .…”

Section: Methodsmentioning

confidence: 99%

Designed synthesis of large-pore crystalline polyimide covalent organic frameworks

et al. 2014

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Covalent organic frameworks (COFs) are an emerging class of porous crystalline polymers with a wide variety of applications. They are currently synthesized through only a few chemical reactions, limiting the access and exploitation of new structures and properties. Here we report that the imidization reaction can be used to prepare a series of polyimide (PI) COFs with pore size as large as 42 × 53 Å(2), which is among the largest reported to date, and surface area as high as 2,346 m(2) g(-1), which exceeds that of all amorphous porous PIs and is among the highest reported for two-dimensional COFs. These PI COFs are thermally stable up to 530 °C. We also assemble a large dye molecule into a COF that shows sensitive temperature-dependent luminescent properties.

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Section: Methodsmentioning

confidence: 99%

Designed synthesis of large-pore crystalline polyimide covalent organic frameworks

et al. 2014

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“…A variety of arm structures, based on oligophenylene derivatives and coupled with numerous types of cores, have been sieved through in search of candidates for application in electroluminescent devices. During this process such compounds, attached to a benzene core, have been reported to exhibit self‐assembling behavior …”

Section: Star‐shaped π‐Conjugated Systems For Oleds and Light Emittersmentioning

confidence: 99%

Advances in Star‐Shaped π‐Conjugated Systems: Properties and Applications

Jarosz

Łapkowski

Ledwon

2014

Macromol. Rapid Commun.

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Until recently π-conjugated organic materials are based mainly on linear systems. Recent years, however, have brought about increasing interest in molecules boasting a dendritic, branched, or star-shaped architecture. This tendency is a direct result of the ongoing search for materials with progressively better properties. Such compounds, featuring novel, 3D architectures, exhibit a multitude of interesting qualities, making them stand out from well-known materials. The direction of star-shaped compound application is determined by whether they are able to form aggregates, π-stacks. This feature is a source of some astounding properties, coveted in numerous applications. Among this class of compounds high charge mobility, high fluorescence efficiency, and good charge separation are all found. Depending on the structure of the core, the molecule may adopt various types of symmetry. Similarly, the conjugation of orbitals may extend over the whole structure or be interrupted at chosen segments. The number of papers pertaining to star-shaped oligomers and polymers is ascending with each year, evidencing a growing interest in them. Consequently, this Review focuses particularly on the most recent reports concerning modification of the structure and properties of the aforementioned type of compounds, as well as on the development of devices based on them.

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“…Keywords: Pi-conjugated molecules · polymorphism · scanning tunnelling microscopy · self-assembly · triazatrinaphthylenes rigid central core have also been found to form novel longrange 2D self-assembled nanostructures. [10,12] In this context, we recently reported on 5,11,17-triazatrinaphthylenes (denoted herein as TrisKs by analogy to the Celtic triskele symbol meaning "three legs"), novel polyA C H T U N G T R E N N U N G het-A C H T U N G T R E N N U N G eroA C H T U N G T R E N N U N G cyclic molecules with C 3h symmetry. [13] TrisKs are trigonal molecules with a skeleton consisting of a central benzene ring connected to three peripheral branches based on quinoline moieties (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Properties, and Remarkable 2 D Self‐Assembly at the Liquid/Solid Interface of a Series of Triskele‐Shaped 5,11,17‐Triazatrinaphthylenes (TrisK)

Bertrand¹,

Guillot²,

Teulade-Fichou³

et al. 2013

Chemistry A European J

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A series of 5,11,17-triazatrinaphthylene (TrisK) derivatives, large disk-like π-conjugated molecules with C3h symmetry, has been synthesised by following an optimised synthetic pathway. The synthesis was performed by a four-step protocol based on the N-arylation of 1,3,5-tribromobenzene with appropriate anthranilate derivatives. This strategy permits the generation of either chlorinated (TrisK-Cl-OCn) or non-chlorinated (TrisK-H-OCn) alkoxy-substituted derivatives (OCn H2n+1 with n=3, 10, 12 and 16), thus providing additional versatility in the control of the structure-property relationships. The electronic properties of the various TrisK compounds have been characterised in solution by absorption and emission spectroscopies as well as cyclic voltammetry. The crystal structure of 2,8,14-propyloxy-5,11,17-triazatrinaphthylene TrisK-H-OC3 has been determined by X-ray diffraction analysis, which revealed the presence of stabilising weak intermolecular H bonds. Scanning tunnelling microscopy (STM) at the liquid/solid interface has revealed the remarkable 2D self-assembling properties of the TrisK compounds. In particular, it has shown that TrisK-H-OC12 forms three concomitant self-organised 2D phases with different row-packing arrangements. This 2D polymorphism arises from slow ordering due to the presence of three long dodecyloxy chains on the molecular backbone. Individual molecules can be imaged with spectacular intramolecular resolution, thus providing the possibility of correlating the STM features with the calculated charge density distribution.

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Synthesis and 2D self-assembly at the liquid-solid interface of end-substituted star-shaped oligophenylenes

Cited by 23 publications

References 46 publications

Designed synthesis of large-pore crystalline polyimide covalent organic frameworks

Designed synthesis of large-pore crystalline polyimide covalent organic frameworks

Advances in Star‐Shaped π‐Conjugated Systems: Properties and Applications

Synthesis, Properties, and Remarkable 2 D Self‐Assembly at the Liquid/Solid Interface of a Series of Triskele‐Shaped 5,11,17‐Triazatrinaphthylenes (TrisK)

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