Hydrogen-bonded structures from adamantane-based catechols

Kawahata, Masatoshi; Matsuura, Miku; Tominaga, Masahide; Katagiri, Kosuke; Yamaguchi, Kentaro

doi:10.1016/j.molstruc.2018.03.011

Cited by 6 publications

(5 citation statements)

References 58 publications

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“…For example, close-packing of rigid tectons (see refs − , , , , − , , and ) would lead to porous crystalline materials with interstitial volumes occupied by molecules of solvent or other guests. Though the packing pattern of the tectons would typically change in the presence or absence of solvent, numerous examples have demonstrated that those seemingly randomly formed packings could also be used to prepare stable HOFs with permanent porosity (see refs , , , − , , , , − , , , and ).…”

Section: Outlook and Perspectivesmentioning

confidence: 99%

Design Rules of Hydrogen-Bonded Organic Frameworks with High Chemical and Thermal Stabilities

et al. 2022

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Hydrogen-bonded organic frameworks (HOFs), self-assembled from strategically pre-designed molecular tectons with complementary hydrogen-bonding patterns, are rapidly evolving into a novel and important class of porous materials. In addition to their common features shared with other functionalized porous materials constructed from modular building blocks, the intrinsically flexible and reversible H-bonding connections endow HOFs with straightforward purification procedures, high crystallinity, solution processability, and recyclability. These unique advantages of HOFs have attracted considerable attention across a broad range of fields, including gas adsorption and separation, catalysis, chemical sensing, and electrical and optical materials. However, the relatively weak H-bonding interactions within HOFs can potentially limit their stability and potential use in further applications. To that end, this Perspective highlights recent advances in the development of chemically and thermally robust HOF materials and systematically discusses relevant design rules and synthesis strategies to access highly stable HOFs.

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Section: Outlook and Perspectivesmentioning

confidence: 99%

Design Rules of Hydrogen-Bonded Organic Frameworks with High Chemical and Thermal Stabilities

et al. 2022

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“…2-Methoxy-4-vinylphenol (2.98%) and phenol, 4-ethyl-2-methoxy-(0.66%) are a food spice prescribed by GB 2760-1996, which can be used as food additives and fragrances (Xu et al, 2016). Catechols (1.22%) are important chemical intermediates, which are used in manufacture antioxidants, special inks, light stabilizers, rubber hardeners, plating additives, skin antiseptics, fungicides, hair dyes, photographic developers, and other important pharmaceutical intermediates (Kawahata et al, 2018). It is used to manufacture cough, butyl phenol, berberine, and isoproterenol (Roychoudhury et al, 2018).…”

Section: Results and Analysismentioning

confidence: 99%

Pyrolysis molecule of Torreya grandis bark for potential biomedicine

Chen

Yue

Yang

et al. 2019

Saudi Journal of Biological Sciences

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Torreya grandis is a unique tree species in China. Although full use has been made of the timber, the processing and utilization of the bark has not been effective. In order to explore a new way to utilize the bark of Torreya grandis , a powder of T. grandis bark was prepared and analyzed qualitatively and quantitatively. Differential scanning calorimetry (TG) and pyrolysis gas chromatography-mass spectrometry (PY-GC/MS) revealed many bioactive components in the bark of T. grandis, such as acetic acid, 2-methoxy-4-vinyl phenol, D-mannose, and furfural. These substances have potential broad applications in the chemical industry, biomedicine, and food additives. The chemical constituents of the bark of T. grandis suggest a theoretical basis for the future development and utilization of the bark of T. grandis .

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“…Nie and co-workers synthesized photosensitive resins with excellent etching resistance and heat resistance from 1,3-adamantanediol. Additionally, the bis-hydroxy functional groups give 1,3-adamantanediol an advantage in the preparation of polymers. − For example, Fu and co-workers synthesized a polycarbonate using 1,3-adamantanediol and diphenyl phosphoryl chloride, which is an effective halogen-free flame retardant. Zhenhua and co-workers introduced adamantane into the structure of polyimide, which can significantly improve its transparency and heat resistance.…”

Section: Introductionmentioning

confidence: 99%

Practical and Scalable Synthesis of 1,3-Adamantanediol

Hao,

Chen,

Yang

et al. 2024

Org. Process Res. Dev.

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A new method for the efficient synthesis of 1,3-adamantanediol is proposed. It has the advantages of good reaction selectivity, high isolated yield, easy purification, and safe operation. 3-Hydroxyadamantane-1-carboxylic acid reacts first with thionyl chloride to form 1,3-dichloro adamantane, which is then converted to 1,3-adamantanediol in a "triethylamine−water" solution. Three reaction types are involved: chlorination, decarbonylation, and hydrolysis. Under optimal reaction conditions, total isolated yields of up to 95% and purities of up to 99% were achieved. Isolated yields of 100 g per batch have been achieved, with potential for industrial production. We completed the decarbonylation of acyl chloride without the use of a metal catalyst. In addition, the reaction mechanism was investigated by combining experimental data and density functional theory.

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Hydrogen-bonded structures from adamantane-based catechols

Cited by 6 publications

References 58 publications

Design Rules of Hydrogen-Bonded Organic Frameworks with High Chemical and Thermal Stabilities

Design Rules of Hydrogen-Bonded Organic Frameworks with High Chemical and Thermal Stabilities

Pyrolysis molecule of Torreya grandis bark for potential biomedicine

Practical and Scalable Synthesis of 1,3-Adamantanediol

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