Design, synthesis, and self-assembly behavior of C3-symmetry discotic molecules via click chemistry

Ryu, Mi-Hee; Choi, Jin‐Woo; Cho, Byoung-Ki

doi:10.1039/b921685e

Cited by 34 publications

(20 citation statements)

References 36 publications

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“…The synthesis of C 3 ‐symmetric 1,2,3‐triazole‐based discotic molecules 111 a – c was reported by Cho and co‐workers (Scheme ) 105. A threefold “click” reaction was achieved in a single step.…”

Section: Classes Of Heterocycles In Columnar Lcsmentioning

confidence: 99%

“…The synthesis of C 3 -symmetric 1,2,3-triazole-based discotic molecules 111 a-c was reported by Cho and co-workers (Scheme 35). [105] A threefold "click" reaction was achieved in a single step. These molecules were designed in such a way that the conjugation is extended up to the triazole units from the central benzene ring.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

“…First example of discotic LCs using "click" reaction by Cho and co-workers. [105,106] Scheme 36. Synthesis of a triazole-based supramolecular complex exhibiting a columnar mesophase.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

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Advances in Metal‐Free Heterocycle‐Based Columnar Liquid Crystals

Roy

Majumdar

2012

Chemistry A European J

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Liquid crystals are ordered soft materials formed by self-organized molecules and can potentially be used as new functional materials for electron-, ion- or molecular-transport; optical; and bio-active materials. In particular, the columnar liquid crystals are promising candidates used in various optical and electronic devices. For this purpose, design and synthesis of unconventional materials are essential. In this review, we have summarized several approaches for the synthesis of columnar liquid crystals composed of various heterocyclic systems. We also outline their liquid crystalline and other relevant properties, and their suitability for applications in diverse fields.

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Section: Classes Of Heterocycles In Columnar Lcsmentioning

confidence: 99%

Section: Wwwchemeurjorgmentioning

confidence: 99%

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Advances in Metal‐Free Heterocycle‐Based Columnar Liquid Crystals

Roy

Majumdar

2012

Chemistry A European J

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“…10 The 1,2,3-triazole rings 45 that result from the CuAAC may also benefit self-organization and electronic properties of the generated adducts due to their strong dipole and aromatic character. Both, calamitic, [11][12][13] polymeric, 14 and discotic [15][16][17] liquid crystals containing the 1,2,3triazole motive have recently been reported. 50 Surprisingly, neither CuAAC nor thermally activated AAC have been employed for the cross-linking of Langmuir films and mesophases.…”

Section: Introductionmentioning

confidence: 99%

Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by “click” chemistry

et al. 2013

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An intrinsic shortcoming of self-organizing materials is their susceptibility to structural changes by mechanical forces and exposure to chemicals and radiation. Cross-linking of the molecules in the desired supramolecular structure is a generally applicable pathway to structurally more stable materials but is difficult to apply to self-organizing materials because the introduction of cross-linkable groups affects their self-organization and the process of cross-linking may alter the supramolecular structure of the 10 preceding phase. Reported here are the synthesis, thermal properties, and cross-linking of octaalkylthio substituted tetraazaporphyrins that contain either eight terminal azide groups or eight terminal acetylene groups. Synthesis of these compounds requires the preparation of the azide and alkyne containing sidechains and their reaction with 1,2-dicyanoethylene-1,2-dithiolate to the corresponding maleodinitrile intermediates. All maleodinitriles are successfully converted to tetraazaporphyrins by the established Mg 15 templated cyclotetramerization in typical yields of 60-70%. Thermal properties of the metal-free and copper(II) metallated tetraazaporphyrins were studied by thermal gravimetric analysis, polarized optical microscopy, differential scanning calorimetry, and variable temperature powder X-ray diffraction measurements. Azide substituted tetraazaporphyrins with trimethylene and hexamethylene spacers as well as acetylene derivatives with with trimethylene spacers unexpectedly display columnar mesophases over 20 ranges of temperature from 30 ºC to 110 ºC. A thermally activated cross-linking of a hexagonal columnar mesophase by cycloaddition at 65 ºC is demonstrated for a 1:1 mixture of azide and acetylene derivatives. At this temperatures the reaction progresses for up to 48 hours but renders the mesophase insoluble and stable to above 200 ºC. The structure of the mesophase is surprisingly little affected by the cross-coupling process that reaches a conversion of 60% of all azide and acetylene groups based on IR measurements. 25 Conversion of up to 80% of azide and acetylene groups is reached by copper catalysed cross-linking of a 1:1 mixture in solution to generate insoluble polymers. A similar degree of conversion is achieved by copper catalysed cross-linking of a 1:1 mixture as Langmuir film after 3 hours. However, transfer of intact cross-linked Langmuir films onto substrates was not successful.

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“…60 By doing a single click reaction of azido-functionalized Percec-type dendrons with 1,3,5-triethynylbenzene, the extension to a conjugate discotic mesogen consisting of three 1,2,3-triazoles and a central benzene ring was easily achieved (Figure 21). …”

Section: Poly(benzyl Ether) Dendron-based Discotic Lc Materials Usingmentioning

confidence: 99%

Spontaneous bulk organization of molecular assemblers based on aliphatic polyether and/or poly(benzyl ether) dendrons

Cho

2012

Polym J

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This paper reviews our recent research with regard to bulk self-assemblers based on well-defined branched building blocks. Branched molecules/polymers have been known to show different physical properties from conventional linear-shaped polymers. As well as thermal and solution properties, structural modification into branched building blocks also has a significant influence on self-assembling behavior in the bulk states, including solid and liquid crystalline (LC) phases. As a branched component, dendrons/dendrimers with well-defined structures can be ideal candidates for the construction of advanced self-assemblers. Recently, we worked on new assembling systems such as dendron-coils, block codendrimers and discotic LC molecules. In the design, we used aliphatic polyether dendrons in most cases and poly(benzyl ether) dendrons in part. Their bulk assembling and thermal properties were found to be distinct from conventional linear block copolymers and they were dependent upon their chain architectures. To self-assemble into ordered nanostructures, the hybrid assembers were designed to have incompatible blocks, for example, hydrophilic and hydrophobic parts. Furthermore, in some cases an ionic complexation was carried out to maximize the immiscibility between the two different blocks. This review describes the molecular manipulations to engineer the nanoassemblies in bulk and also the ionic transportation properties depending on the assembling morphology.

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Design, synthesis, and self-assembly behavior of C3-symmetry discotic molecules via click chemistry

Cited by 34 publications

References 36 publications

Advances in Metal‐Free Heterocycle‐Based Columnar Liquid Crystals

Advances in Metal‐Free Heterocycle‐Based Columnar Liquid Crystals

Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by “click” chemistry

Spontaneous bulk organization of molecular assemblers based on aliphatic polyether and/or poly(benzyl ether) dendrons

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