Preparation of Highly Hindered Polyenynes

Kılıçkıran, Pınar; Hopf, Henning; Dix, Ina; Jones, Peter G.

doi:10.1002/ejoc.201000018

Cited by 6 publications

(6 citation statements)

References 13 publications

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“…Reactions of polyynes higher than butadiynes with sodium sulfide are rare and usually mixtures of different products are obtained. 32 Emission Spectroscopy. Some of the presented thiophenes exhibit strong photoluminescence upon the UV irradiation, thus we recorded absorption and emission/ excitation spectra for all the new thiophenes.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Our work is the first synthesis of thiophenes from polyyneamines and may be considered as a complementary addition to Witulski’s results and is the first synthesis of 2-amino-5-phenylthiophenes and 2-amino-5-phenylethynylthiophenes from butadiynes and hexatriynes. Reactions of polyynes higher than butadiynes with sodium sulfide are rare and usually mixtures of different products are obtained …”

Section: Results and Discussionmentioning

confidence: 99%

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Use of Stable Amine-Capped Polyynes in the Regioselective Synthesis of Push–Pull Thiophenes

et al. 2017

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The reactions of a series of 1-halopolyynes with secondary amines led to novel amine end-capped polyynes exhibiting surprisingly high stability toward moisture. The new compounds were characterized by NMR spectroscopy, ESI-MS spectrometry, and X-ray single-crystal diffractometry. The use of amine end-capped polyynes as precursors to substituted push-pull thiophenes was next presented. The results show the first-to the best of our knowledge-transformation of ynamine to thiophene and the first regioselective transformation of a longer polyynes to butadiyne-substituted thiophene. Photophysical studies of the resulting compounds show that some of the substituted thiophenes have high quantum yield photoluminescence upon UV light irradiation.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Use of Stable Amine-Capped Polyynes in the Regioselective Synthesis of Push–Pull Thiophenes

et al. 2017

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“…Double reaction for octatetraynes is also possible. [80] Very recently we have reported regioselective transformation of surprisingly stable amine endcapped polyynes into substituted thiophenes 134-142. [79] However, octatetraynes not always give selectively one product.…”

Section: Formation Of Heterocyclesmentioning

confidence: 99%

“…It was reported that the reaction of organic octatetrayne 130 with Na 2 S was not regioselective and led to a mixture of different thiophene and bithiophene species (131)(132)(133). [80] Very recently we have reported regioselective transformation of surprisingly stable amine endcapped polyynes into substituted thiophenes 134-142. [81] In this reaction, two triple bonds directly attached to nitrogen are selectively transformed into thiophene ring.…”

Section: Formation Of Heterocyclesmentioning

confidence: 99%

Reactivity of Polyynes: Complex Molecules from Simple Carbon Rods

2019

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Polyynes are linear carbon rods that may be regarded as models of carbyne – still elusive linear allotropic form of carbon. This microreview addresses the use of polyynes as synthetic precursors of complex organic and organometallic compounds. Application of such unusual molecules as starting materials for various chemical transformations leads to products which often are not easily accessible using “traditional“ approaches. Polyynes may for instance be used in the synthesis of molecular wires, materials possessing high nonlinear optical response, complex donor–acceptor systems, solvatochromic fluorescent dyes or natural products. The most significant challenge here is to control the regioselectivity of a transformation of such linear sp‐hybridized carbon chains. The impact of steric and electronic properties of reagents on the reaction pattern is hence highly important and will be discussed. Moreover, the transformations of end‐groups will also be addressed since their reactivity might very often be different than that of acetylenes.

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“…Despite the synthetic inaccessibility of longer analogues, hexatriynyl- and octatetraynyl-substituted pyrroles were investigated with the use of computational methods . Moreover, such heterocyclic-long conjugated systems may be used as very useful substrates for the synthesis of oligoheterocycles …”

Section: Introductionmentioning

confidence: 99%

Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles

et al. 2016

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In this contribution, the synthesis of long chain hexatriynyl- and octatetraynyl-substituted pyrroles in one step from 1-halopolyyne precursors is reported. The products were obtained via a mechanochemical approach by simple grinding of 1-haloalkynes with N-substituted pyrroles and potassium carbonate which played a role of heterogeneous catalyst and this solvent- and transition metal-free approach is unprecedent in the synthesis of new, organic, long chain polyynes. Additionally, an extensive X-ray single crystal study of pyrrole end-capped polyynes is presented. Such compounds are possible substrates for different oligoheterocycles and have a significant application potential such as for instance molecular wires.

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Preparation of Highly Hindered Polyenynes

Cited by 6 publications

References 13 publications

Use of Stable Amine-Capped Polyynes in the Regioselective Synthesis of Push–Pull Thiophenes

Use of Stable Amine-Capped Polyynes in the Regioselective Synthesis of Push–Pull Thiophenes

Reactivity of Polyynes: Complex Molecules from Simple Carbon Rods

Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles

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