Synthesis and physical properties of triptycene-based oligo(p-phenyleneethynylene)s

Zeng, Fei; Tang, Lin-Li; Chen, Xiaoming; Ding, Ming‐Wu

doi:10.1016/j.tet.2018.10.011

Cited by 3 publications

(3 citation statements)

References 43 publications

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“…From the 1,4-dihydroxy tripmonomer (54), a para-benzoquinone derivative (59) can be obtained by oxidation, and from the imine derivative (60), it can be prepared through condensation with hydroxylamine, which can be subsequently reduced to yield the 1,4-diamino trip-monomer (61) [49,50]. Compound 61 can undergo a Sandmeyer-type reaction to yield the 1,4-diiodo tripmonomer (62) [48], which has been used in a further Sonogashira reaction to synthesize the 1,4-diethynyl tripmonomer (57) [51,52]. The para-benzoquinone form of pentiptycene ( 64) can be synthesized using an excessive amount of anthracene in a Diels-Alder reaction with parabenzoquinone or by allowing the para-benzoquinone form of triptycene to undergo a second Diels-Alder reaction with anthracene in acetic acid [16,48].…”

Section: Synthetic Routes For Accessing Triptycene Derivatives and Tr...mentioning

confidence: 99%

Recent advances in structurally elaborate triptycenes, triptycene-containing polymers and assemblies: structures, functions and applications

Ishiwari,

Shoji,

Martin

et al. 2024

Polym J

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Triptycene, a rigid propeller-shaped molecule, was first synthesized in the early 1940s. More recently, many triptycene-containing polymers and molecular assemblies have been developed for a wide range of applications, including guest recognition, material transport, separation, catalysis, and as device components. The advantages of triptycenes lie in their ability to introduce a variety of functional groups on their three-dimensional backbone, with changes in substitution patterns as well as the type of substituents present having a significant impact on the material properties. In this review, we describe the synthesis of triptycene derivatives and polymers, detailing selected examples of triptycene-containing functional polymers. We also focus on the construction of triptycene-based two-dimensional assemblies and polymers, where space-filling designs based on rigid propeller-shaped skeletons are essential. Through a thorough literature survey, future directions and possibilities for the development of triptycene-containing functional materials are discussed.

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Section: Synthetic Routes For Accessing Triptycene Derivatives and Tr...mentioning

confidence: 99%

Recent advances in structurally elaborate triptycenes, triptycene-containing polymers and assemblies: structures, functions and applications

Ishiwari,

Shoji,

Martin

et al. 2024

Polym J

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“…55 This is problematic from a materials design perspective, as the solid-state optical properties are heavily influenced by this packing, often resulting in shifting of emission and aggregation-caused quenching (ACQ). [56][57][58] Our group has demonstrated that programmed aromatic stacking interactions between non-conjugated fluorinated arene side-chains and main-chain arene groups can control solid-state packing of phenylene-ethynylenes PEs. [59][60][61][62][63] In agreement with prior work showing that the electrostatic complementary of arene rings plays a pivotal role in determining the likelihood of aromatic stacking, 64,65 our prior study on electronic substituent effects for ArF-ArH stacking demonstrated the need for electronic complementarity between stacking partners.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Crystal engineering of heterocyclic arylene(ethynylene) oligomers through programmed aromatic stacking

et al. 2022

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A.E.Favorskii’s scientific legacy in modern organic chemistry: prototropic acetylene – allene isomerization and the acetylene zipper reaction

Danilkina¹,

Vasil'eva²,

Балова³

2020

Russ. Chem. Rev.

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Alexei Evgrafovich Favorskii was an outstanding organic chemist who left a great scientific legacy as a result of long time and fruitful work. Most of the theoretically and practically important discoveries of A.E.Favorskii were made in the chemistry of acetylene and its derivatives. Nowadays, the reactions discovered by him, which include acetylene – allene isomerization, the Favorskii and retro-Favorskii reactions, the Favorskii rearrangement and the vinylation reaction, are widely used in industry and in laboratory synthesis. This review summarizes the main scientific achievements of A.E.Favorskii, as well as their development in modern organic chemistry. Much consideration is given to acetylene – allene isomerization as a convenient method for the synthesis of methyl-substituted acetylenes and to the acetylene zipper reaction as a synthetic tool for obtaining terminal acetylenes. The review presents examples of the application of these reactions in modern organic synthesis of complex molecules, including natural compounds and their analogues. The bibliography includes 266 references.

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Synthesis and physical properties of triptycene-based oligo(p-phenyleneethynylene)s

Cited by 3 publications

References 43 publications

Recent advances in structurally elaborate triptycenes, triptycene-containing polymers and assemblies: structures, functions and applications

Recent advances in structurally elaborate triptycenes, triptycene-containing polymers and assemblies: structures, functions and applications

Crystal engineering of heterocyclic arylene(ethynylene) oligomers through programmed aromatic stacking

A.E.Favorskii’s scientific legacy in modern organic chemistry: prototropic acetylene – allene isomerization and the acetylene zipper reaction

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