Complementary Hydrogen Bonding Between a Clicked <i>C</i><sub>3</sub>‐Symmetric Triazole Derivative and Carboxylic Acids for Columnar Liquid‐Crystalline Assemblies

Ryu, Mi-Hee; Choi, Jin‐Woo; Kim, Ho-Joong; Park, Noejung; Cho, Byoung-Ki

doi:10.1002/anie.201101013

Cited by 54 publications

(45 citation statements)

References 35 publications

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“…In the field of mesogenic materials, some liquid crystals containing the 1,2,3-triazole ring have been synthesized, and exhibit multiform liquid-crystalline mesophases with a lower melting temperature and a wide thermal range useful in device applications [14][15][16][17][18][19][20]. Recently, we have reported a series of 1,2,3-(NH)-triazolyl ferrocenomesogens with good redox activity [21].…”

Section: Introductionmentioning

confidence: 98%

Electrochemistry and liquid crystal properties of mono-substituted 1,2,3-triazolylferrocene derivatives

Zhao

Liu

Chuo

et al. 2015

Journal of Molecular Liquids

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Section: Introductionmentioning

confidence: 98%

Electrochemistry and liquid crystal properties of mono-substituted 1,2,3-triazolylferrocene derivatives

Zhao

Liu

Chuo

et al. 2015

Journal of Molecular Liquids

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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%

“…29 Photopolymerization was not successful, most likely because the light was preferentially absorbed by the phthalocyanine core. However, this work has not been pursued much further because the generated materials were contaminated by the required radical initiator, typically AIBN, 15 and the fast progress of the cross-linking reaction generates defects and cracks in the material. Müllen et al recently succeeded in the photochemical and thermal polymerization of a columnar mesophases of an acrylate substituted hexabenzocoronene derivative without the aid of a 20 photoinitiator.…”

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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“…One-or two-dimensional open-type columnar LCs are also introduced, and they are formed by assembly through hydrogen bonds between the neighboring stacked molecules. Some of these systems may have potential application as electronics and nanoporous organic materials owing to the columnar morphology and the dynamic nature of the H-bonding [75]. One-dimensional columnar phase might show one-dimensional high photoconductivity and ion transporting ability and can be used as dynamic mass and charge transporting materials because of their self-assembling nature.…”

mentioning

confidence: 99%

“…Park and Cho et al have prepared novel hydrogen bonded complexes (58) consisting of a clicked C 3 -symmetric 1,3,5-tris(1-alkyl-1H-1,2,3-triazol-4-yl)benzene (TTB) core unit with three 3,4,5-trioctyloxy-benzoic acids (TBAs). The complexes form hexagonal columnar LC phases which may be applicable for electronics and nanoporous organic materials owing to the columnar morphology and the dynamic nature of the H-bonding [75].…”

mentioning

confidence: 99%

Hydrogen Bonding for Supramolecular Liquid Crystals

Cheng

Gao

2015

Lecture Notes in Chemistry

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This chapter reviews the recent development on hydrogen bonded supramolecular low molecular weight liquid crystals (LCs), including hydrogen bonded rodlike and bent-shaped supramolecular LCs, columnar LCs, as well as nonconventional liquid crystals. IntroductionLiquid crystals (LCs) combine order and mobility on a molecular level and are important both in material and life science [1][2][3][4][5][6][7][8][9]. Different liquid crystalline phases have provided new methods for the design of supramolecular materials [10][11][12][13]. Nematic phases have found widely commercial applications as displays for computers and telecommunications [14], lamellar, columnar, micellar, and bicontinuous cubic phases and even more complicated new phases have also found wide applications as advanced materials [12,[15][16][17].Supramolecular liquid crystals can be obtained through hydrogen bonding, which was first introduced by Kato, and Lehn [21]. They exhibit a variety of physical properties, which make them attractive for applications in the field of nanoscience, materials, and biology and offer a very elegant and effective approach to adding functionalization in a controllable and convenient way to the molecular architecture. Complex 1 that exhibits smectic and nematic phases [18] and complex 2 that shows a columnar phase [21] are the two earliest examples for supramolecular hydrogen bonded liquid crystals. The design principle of hydrogen bonded supramolecule was also applied to prepare side-chain polymers 3 [19,20] and main-chain liquid crystal polymer 4 [22] and 5 [23], in this way the field of supramolecular polymers was introduced [24][25][26].

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Complementary Hydrogen Bonding Between a Clicked C₃‐Symmetric Triazole Derivative and Carboxylic Acids for Columnar Liquid‐Crystalline Assemblies

Cited by 54 publications

References 35 publications

Electrochemistry and liquid crystal properties of mono-substituted 1,2,3-triazolylferrocene derivatives

Electrochemistry and liquid crystal properties of mono-substituted 1,2,3-triazolylferrocene derivatives

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

Hydrogen Bonding for Supramolecular Liquid Crystals

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Complementary Hydrogen Bonding Between a Clicked C3‐Symmetric Triazole Derivative and Carboxylic Acids for Columnar Liquid‐Crystalline Assemblies

Cited by 54 publications

References 35 publications

Electrochemistry and liquid crystal properties of mono-substituted 1,2,3-triazolylferrocene derivatives

Electrochemistry and liquid crystal properties of mono-substituted 1,2,3-triazolylferrocene derivatives

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

Hydrogen Bonding for Supramolecular Liquid Crystals

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Complementary Hydrogen Bonding Between a Clicked C₃‐Symmetric Triazole Derivative and Carboxylic Acids for Columnar Liquid‐Crystalline Assemblies