Synthesis and properties of some novel unsymmetrically substituted diacetylenes

Milburn, G. H. W.; Werninck, A. R.; Tsibouklis, John; Bolton, E. C.; Thomson, G. A.; Shand, Angie

doi:10.1016/0032-3861(89)90070-0

Cited by 25 publications

(11 citation statements)

References 9 publications

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“…An aspect of the substituent effect that has received little attention is the influence of formally p-conjugated substituents on the electronic properties of poly-1,3-diynes. This is because many of them are unreactive in the solid state, [4][5][6] although they do undergo liquid crystal polymerization. Moreover, 4-aminophenyl-4nitrophenylbuta-1,3-diyne is solid-state reactive.…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, 4-aminophenyl-4nitrophenylbuta-1,3-diyne is solid-state reactive. 6 The discovery of a one-dimensional metallic state in the ion-radical solid formed from the p-donor tetrathiofulvalene and the acceptor tetracyanoquinodimethane has stimulated interest in the structure-property relationships of novel donors and acceptors. 7 Although the metallic conductivity and superconductivity of these organic charge-transfer salts are the most important properties, recently attention has also been directed to the novel magnetic and optical properties which they can display (review 8 ).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and structural analysis of 1,4‐bis[n‐(N,N‐dimethylamino)phenyl]buta‐1,3‐diynes and charge‐transfer complexes with TCNE

Rodriguez

Lafuente

Martı́n-Villamil

et al. 2001

J of Physical Organic Chem

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n-(N,N-Dimethylamino)phenylethynes were satisfactorily prepared by a Wittig reaction between chloromethylene(triphenyl)phosphine ylide and the appropriate n-(N,N-dimethylamino)benzaldehyde, followed by dehydrochlorination with a strong base. The conjugate dimers 1,4-bis[n-(N,N-dimethylamino)phenyl]buta-1,3-diyne were obtained by oxidative dimerization with copper(I) chloride. X-ray molecular structure analysis of the dimer 1,4bis[2-(N,N-dimethylamino)phenyl]buta-1,3-diyne corroborated the resonance contribution of the o-dimethylamino substituent, which was confirmed in the solid state by the molecular crystalline packing. Both o-and p-(N,Ndimethylamino) conjugate dimers develop 1:1 charge-transfer complexes with TCNE and their structure was identified by NMR, IR and UV-visible spectroscopic data. Differential scanning calorimetric analyses of the 1,3diynes showed an irreversible transformation to a thermopolymer as a unimolecular reaction.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and structural analysis of 1,4‐bis[n‐(N,N‐dimethylamino)phenyl]buta‐1,3‐diynes and charge‐transfer complexes with TCNE

Rodriguez

Lafuente

Martı́n-Villamil

et al. 2001

J of Physical Organic Chem

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“…紫外光辐射下能发生聚合 [32] . 直接与炔基相连的两个苯环上分别含有推电子基团和供电子基团的丁二炔类衍生物, 化合物60 [33] 和61 [34] , 但是它们的聚合活性却不同: 化合物60在加热或光照可以发生固相拓扑聚合反应, 而化合物61在加热时却显示液晶的…”

Section: 化合物16~24是取代基中含有磺酸酯基团对称取代的unclassified

Topochemical polymerization of diacetylenes

Yao

Qiu

et al. 2016

Chin. Sci. Bull.

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“…1 The polymerization of diacetylenes has been of great interest because it was reported 2,3 that the solid-state reaction proceeds via a topochemical 1,4-addition. Generally, most PDAs are insoluble even in exotic solvents, and infusible.…”

Section: Introductionmentioning

confidence: 99%

Preparation and structure/property relationships of polyesters containing conjugated diacetylene groups

1999

J. Polym. Sci. B Polym. Phys.

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A series of novel polyesters containing conjugated diacetylenes (DA‐polyesters) were prepared from various diacetylene diols with/without methyl side groups and isomers of aromatic acid chlorides via an interfacial condensation. A fully aliphatic DA‐polyester was also prepared for comparison. All synthesised DA‐polyesters are soluble in m‐cresol, and the intrinsic viscosities were measured. In addition, compact and coherent films and sheets can be obtained from some of the polymers via solution or melt casting. The structure, morphology, and properties were characterized using spectroscopic methods, including FTIR, Raman, and WAXD and thermal analysis including TGA, DSC techniques. DMA was carried out on the solution‐cast thin films and melt‐processed samples. Close correlation was found between the structure and properties in these DA‐polyesters. In particular, through analysis using isothermal DSC and Raman spectroscopy, the solid‐state reactivity of the diacetylene groups in these polyesters was found related to the interchain spacings, which are, in turn, controlled by the molecular structure of the polymers. Results have shown that the aliphatic DA‐polyester behaves very differently compared to the aromatic ones. Distinct differences were also observed among meta‐ and para‐disubstituted isomers of the DA‐polyesters. Furthermore, the introduction of methyl side groups has dramatically affected the thermal and thermal mechanical behavior by altering the interchain spacing of the polymers. © 1999 John Wiley & Sons, Inc. J Polym Sci B: Polym Phys 37: 965–974, 1999

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Synthesis and properties of some novel unsymmetrically substituted diacetylenes

Cited by 25 publications

References 9 publications

Synthesis and structural analysis of 1,4‐bis[n‐(N,N‐dimethylamino)phenyl]buta‐1,3‐diynes and charge‐transfer complexes with TCNE

Synthesis and structural analysis of 1,4‐bis[n‐(N,N‐dimethylamino)phenyl]buta‐1,3‐diynes and charge‐transfer complexes with TCNE

Topochemical polymerization of diacetylenes

Preparation and structure/property relationships of polyesters containing conjugated diacetylene groups

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