Eine neue Triptycen‐Synthese

Wittig, Georg; Benz, E.

doi:10.1002/ange.19580700612

Cited by 10 publications

(7 citation statements)

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“…29 The name iptycene originated from the basic unit triptycene, which was first synthesized and named by Bartlett and coworkers in 1942. 30 Later, triptycene has become readily available thanks to the well known work of Wittig 31, 32 on the preparation of dehydrobenzene (benzyne) and its interaction with anthracene. The chemistry of triptycene has been studied in comparative detail and has been summarized in an earlier review article reported by the Russian researchers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of novel triptycene‐based polyimides

Hsiao

Wang

Chen

et al. 2011

J. Polym. Sci. A Polym. Chem.

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Two new triptycene‐containing bis(ether amine)s, 1,4‐bis(4‐aminophenoxy)triptycene (4) and 1,4‐bis(4‐amino‐2‐trifluoromethylphenoxy)triptycene (6), were synthesized, respectively, from the nucleophilic chloro‐displacement reactions of p‐chloronitrobenzene and 2‐chloro‐5‐nitrobenzotrifluoride with 1,4‐dihydroxytriptycene in the presence of potassium carbonate, followed by palladium‐catalyzed hydrazine reduction of the dinitro intermediates. The bis(ether amine)s were polymerized with six commercially available aromatic tetracarboxylic dianhydrides to obtain two series of novel triptycene‐based polyimides 8a–f and 9a–f by using a conventional two‐step synthetic method via thermal and chemical imidizations. All the resulting polyimides exhibited high enough molecular weights to permit the casting of flexible and strong films with good mechanical properties. Incorporation of trifluoromethyl groups in the polyimide backbones improves their solubility and decreases their dielectric constants. The fluorinated polyimides 9d and 9f derived from diamine 6 with 4,4′‐oxydiphthalic anhydride and 2,2‐bis(3,4‐dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), respectively, could afford almost colorless thin films. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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Section: Introductionmentioning

confidence: 99%

Synthesis and properties of novel triptycene‐based polyimides

Hsiao

Wang

Chen

et al. 2011

J. Polym. Sci. A Polym. Chem.

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“…The triptycene fragment is generally obtainedb ya[4+ +2] cycloaddition of ab enzyne species (prepared in situ) onto an anthracene unit. [18] Benzynes can be obtained by reaction of magnesium with 1-bromo-2-fluorobenzene, [18] reaction of BuLi with fluorobenzene, [19] from oxadisilols, [20] from iodonium ortho-benzoate, [18] or by reaction of anthranilic acidw ith isopentyl nitrite. [7b] By modification of ap ublished procedure, [21] we used this latter method to obtain 1 in three steps from commercially available 9,10-dibromoanthracene.…”

Section: Synthesis Ofmentioning

confidence: 99%

Synthesis of Functionalized Mono‐, Bis‐, and Trisethynyltriptycenes for One‐Dimensional Self‐Assembly on Surfaces

Sirven

Garbage

Qiao

et al. 2015

Chemistry A European J

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This paper describes the synthesis of triptycene-based building blocks that are able to interact through hydrogen bonds to form one-dimensional self-assembled motifs on surfaces. We designed 9,10-diethynyltriptycene derivatives functionalized at the ethynyl end groups by a variety of hydrogen-bonding groups for homomolecular recognition and complementary building blocks for heteromolecular recognition. We also present the synthesis of bis- and trisethynyltriptycenes with terminal alkyne functional groups available for on-surface azide-alkyne cycloaddition reaction to expand the potential of the triptycene building block.

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“…The present synthesis of triptycene is considerably shorter than the elegant classical synthesis by Bartlett, Ryan, and Cohen.1 345Further, it shows promise of being more generally applicable to the synthesis of bridgehead substituted triptycenes than the ingeneous syntheses through benzyne by Wittig and co-workers. [2][3][4] The details of the present route and its extension to substituted triptycenes are being investigated.…”

Section: Department Of Biologicalmentioning

confidence: 99%