Theoretical research of covalent and controllable molecular brake based on 9-triptycene

Wang, Hailong; Guan, Qiuping; Wang, Xueye

doi:10.1007/s00214-021-02762-9

Cited by 2 publications

(2 citation statements)

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“…Similarly, 2-hydroxy-7-methoxynapthalene reacts with phthalaldehyde to give a mixture of the isomeric products 1,7'-dihydroxy-6,2'-dimethoxy-naphthopleiadene (4a) and 1,2'-dihydroxy-6,7'-dimethoxy-naphthopleiadene (4b), which could be separated by using the relatively poor solubility of the former in acetone. The same reaction conditions using 2,7dimethoxnaphthalene and phthalaldehyde failed to provide 1,6,2',7'tetramethoxynaphthopleiadene (5). However, by adapting an efficient preparation of methoxysubstituted triphenylmethanes, 35 using BF3.OEt2 in dichloromethane, NP 5 was obtained in moderate yield with its structure confirmed by single crystal XRD analysis.…”

Section: Resultsmentioning

confidence: 96%

“…However, by adapting an efficient preparation of methoxysubstituted triphenylmethanes, 35 using BF3.OEt2 in dichloromethane, NP 5 was obtained in moderate yield with its structure confirmed by single crystal XRD analysis. 2,3,8,9,14,6,11,12,17,K2CO3,DMF,120 °C,48 h. (d) 2,3,5,K2CO3,DMF,160 h. The structure of NP 1, with a short distance between adjacent hydroxyl groups (O to O distance = 2.74 Å), suggested a similar reactivity to that of the resorcinarenes, for which Cram demonstrated deep cavitand formation using the efficient reaction with 2,3-dichloroquinoxaline (Fig. 3a).…”

Section: Resultsmentioning

confidence: 99%

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Rapid access to triptycene-like naphthopleiadenes for use in supramolecular and materials chemistry

Amin,

Ye,

Pang

et al. 2023

Preprint

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Triptycene derivatives are used extensively in supramolecular and materials chemistry, however, most are prepared using a multi-step synthesis that involves the generation of a benzyne intermediate, which hinders scale-up. Inspired by the ease of resorcinarene synthesis, we report the rapid and efficient preparation of triptycene-like 1,6,2’,7’-tetrahydroxynaphthopleiadene directly from 2,7-dihydroxynaphthalene and phthalaldehyde. Structural characterisation confirms the novel bridged bicyclic framework, within which the planes of the single benzene ring and two naphthalene units are fixed at an angle of ~120° relative to each other. Several simple variations of aromatic 1,2-dialdehydes and 2,7-disubstituted naphthalenes also provided triptycene-like products. The low cost of the precursors and undemanding reaction conditions allows for rapid multigram synthesis of 1,6,2’,7’-tetrahydroxynaphthopleiadene with product isolation by simple filtration. The potential for its use in supramolecular and polymer chemistry was demonstrated by the preparation of a very rigid novel cavitand, a microporous network polymer, and a solution-processable polymer of Intrinsic microporosity.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%