- Synthesis of organoplatinum poly (dendrimer)s: Pronounced effect of size and geometry of small organoplatinum linkers on the copolymerization efficiency with bifunctional dendritic macromonomers
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The copolymerizations of two series of surface functionalized bis(acetylene) G1-G3 dendrimers, one (S-Gn) having a structural rigid skeleton and the other (L-Gn) a relatively more flexible architecture, with two platinum linkers, cis-[(Et2PCH2CH2PEt 2)PtCl2] (2) and [Cl-(Et3P)2Pt- C≡C-P-C6H4-], (3) were investigated. For both series of dendrimers, only linear and/or cyclic oligomers were formed when the cis-platinum linker 2 was used. However, high molecular weight (100-200 kD) organoplatinum poly(dendrimer)s were obtained from both series when the elongated linear rod-liked platinum linker 3 was employed and the formation of cyclic oligomers was greatly suppressed for both the structural rigid S-Gn and the structural flexible L-Gn series. These results are in sharp contrast to our earlier findings (S.-Y. Cheung, H.-F. Chow, T. Ngai, X. Wei, Chem. Eur. J. 2009, 75, 2278-2288) obtained by using a shorter linear platinum linker trans-[Pt-(PEt3)2Cl2] (1), where a larger amount of cyclic oligomers was formed from the structural flexible L-Gn dendrimers. A model was proposed to rationalize how the geometry and size of the platinum linker could control the copolymerization behaviours of these dendritic macromonomers.
- Cheung, Siu-Yin,Chow, Hak-Fun
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- Simple synthesis, outstanding thermal stability, and tunable light-emitting and optical-limiting properties of functional hyperbranched polyarylenes
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The synthesis, thermal stability and optical properties of functional hyperbranched polyarylenes were reported. The molecular structure of the polymers was determined by nuclear magnetic resonance (NMR) spectroscopy. The spectra showed that the hyperbranched polymers possessed a random molecular composition, an irregular stereostructure and a rigid core architecture. The optical limiting and tunable light emitting properties of the polymers make them suitable to be used for high-tech applications.
- Peng, Hah,Cheng, Lin,Luo, Jingdong,Xu, Kaitian,Sun, Qunhui,Dong, Yuping,Salhi, Fouad,Lee, Priscilla P.S.,Chen, Junwu,Tang, Ben Zhong
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- Synthetic control of the pore dimension and surface area in conjugated microporous polymer and copolymer networks
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A series of rigid microporous poly(aryleneethynylene) (PAE) networks was synthesized by Sonogashira-Hagihara coupling chemistry. PAEs with apparent Brunauer-Emmet-Teller surface areas of more than 1000 m2/g were produced. The materials were found to have very good chemical and thermal stability and retention of microporosity under a variety of conditions. It was shown that physical properties such as micropore size, surface area, and hydrogen uptake could be controlled in a "quantized" fashion by varying the monomer strut length, as for metal-organic and covalent organic frameworks, even though the networks were amorphous in nature. For the first time, it was demonstrated that these properties can also be fine-tuned in a continuous manner via statistical copolymerization of monomer struts with differing lengths. This provides an unprecedented degree of direct synthetic control over micropore properties in an organic network.
- Jiang, Jia-Xing,Su, Fabing,Trewin, Abbie,Wood, Colin D.,Niu, Hongjun,Jones, James T. A.,Khimyak, Yaroslav Z.,Cooper, Andrew I.
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- Micellar and vesicular nanoassemblies of triazole-based amphiphilic probes triggered by mercury(II) ions in a 100% aqueous medium
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ABA-type amphiphiles bearing a triazole-based aromatic block were easily synthesized using click chemistry, which act as fluorescent turn-off Hg2+-chemoprobes in an aqueous solution. Interestingly, the metal-binding process of amphiphiles induc
- Kim, Inhye,Lee, Na-Eun,Jeong, Yoo-Jeong,Chung, Young-Ho,Cho, Byoung-Ki,Lee, Eunji
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- Conformational Tuning of the Intramolecular Electronic Coupling in Molecular-Wire Biruthenium Complexes Bridged by Biphenyl Derivatives
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The synthesis and characterization of a series of biphenyl-derived binuclear ruthenium complexes with terminal {RuCl(CO)(PMe3)3} moieties and different structural arrangements of the phenyl rings are reported. Electrochemical studies
- Kong, Dan-Dan,Xue, Lu-Sha,Jang, Rui,Liu, Bin,Meng, Xiang-Gao,Jin, Shan,Ou, Ya-Ping,Hao, Xiao,Liu, Sheng-Hua
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- Allosteric regulation of rotational, optical and catalytic properties within multicomponent machinery
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The reversible transformation of multicomponent nanorotors (ROT-1, k298 = 44 kHz or ROT-2, k298 = 61 kHz) to the "dimeric"supramolecular structures (DS-1 or DS-2, k298 = 0.60 kHz) was triggered by a stoichiometric chemical stimulus. Simple coordination changes at the central phenanthroline of the molecular device by altering metal ions (Cu+ → Zn2+) or stoichiometry (Cu+, 1 equiv. → 0.5 equiv.) affected the terminal zinc(ii) porphyrin units, the active sites within the machinery, changing rotational, catalytic and optical properties. In presence of added pyrrolidine, the nanorotor ROT-1 was inactive for catalysis whereas formation of the dimeric supramolecular structures DS-1 initiated a Michael addition reaction by releasing the organocatalyst from the porphyrin sites. This catalytic machinery (ROT-1 ? DS-1) proved to reproducibly work over two full cycles using allosteric OFF/ON control of catalysis. This journal is
- Ghosh, Amit,Paululat, Thomas,Saha, Suchismita,Schmittel, Michael
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- Understanding the Role of Parallel Pathways via In-Situ Switching of Quantum Interference in Molecular Tunneling Junctions
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This study describes the modulation of tunneling probabilities in molecular junctions by switching one of two parallel intramolecular pathways. A linearly conjugated molecular wire provides a rigid framework that allows a second, cross-conjugated pathway
- Asyuda, Andika,Chiechi, Ryan C.,Hong, Wenjing,Soni, Saurabh,Ye, Gang,Zhang, Yanxi,Zharnikov, Michael,Zheng, Jueting
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- Modular Approach to Kekulé Diradicaloids Derived from Cyclic (Alkyl)(amino)carbenes
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A modular approach for the synthesis of Kekulé diradicaloids is reported. The key step is the insertion of a carbene, namely, a cyclic (alkyl)(amino)carbene (CAAC), into the C-H bonds of two terminal alkynes linked by a spacer. Subsequent hydride abstraction, followed by two-electron reduction of the corresponding bis(iminium) salts, affords the desired diradicaloids. This synthetic route readily allows for the installation of communicating spacers, featuring different degrees of aromaticity and lengths, and gives the possibility of generating unsymmetrical compounds with two different CAACs. Electron paramagnetic resonance (EPR), NMR, UV-vis, and X-ray studies in combination with quantum-chemical calculations give insight into the electronic nature of the deeply colored Kekulé diradicaloids. They feature a singlet ground state with varying degrees of diradical character in combination with small singlet/triplet gaps. Upon lengthening of the spacer, the properties of the compounds approach those of monoradicals in which steric protection of the propargyl radical moiety is necessary to inhibit decomposition pathways. Most of these diradicaloids are stable at room temperature, both in solution and in the solid state, but are highly oxygen-sensitive. They represent the first diradicaloids derived from iminium salts.
- Hansmann, Max M.,Melaimi, Mohand,Munz, Dominik,Bertrand, Guy
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supporting information
p. 2546 - 2554
(2018/02/28)
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- Efficient Homocoupling of Aryl- and Alkenylboronic Acids in the Presence of Low Loadings of [{Pd(μ-OH)Cl(IPr)} 2 ]
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NHC-palladium(II) complex [{Pd(μ-OH)Cl(IPr)} 2 ] (IPr = bis(2,6-diisopropylphenyl)imidazolin-2-ylidene) catalyzes the oxidative coupling of a broad spectrum of aryl- and alkenylboronic acids at loadings down to 5 ppm. At the concentration of 0.05 mol% the catalyst permits an efficient reaction under base-free conditions.
- Ostrowska, Sylwia,Rogalski, Szymon,Lorkowski, Jan,Walkowiak, Jedrzej,Pietraszuk, Cezary
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supporting information
p. 1735 - 1740
(2018/07/21)
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- Highly Stable, Low Gas Crossover, Proton-Conducting Phenylated Polyphenylenes
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Two classes of novel sulfonated phenylated polyphenylene ionomers are investigated as polyaromatic-based proton exchange membranes. Both types of ionomer possess high ion exchange capacities yet are insoluble in water at elevated temperatures. They exhibit high proton conductivity under both fully hydrated conditions and reduced relative humidity, and are markedly resilient to free radical attack. Fuel cells constructed with membrane-electrode assemblies containing each ionomer membrane yield high in situ proton conductivity and peak power densities that are greater than obtained using Nafion reference membranes. In situ chemical stability accelerated stress tests reveal that this class of the polyaromatic membranes allow significantly lower gas crossover and lower rates of degradation than Nafion benchmark systems. These results point to a promising future for molecularly designed sulfonated phenylated polyphenylenes as proton-conducting media in electrochemical technologies.
- Adamski, Michael,Skalski, Thomas J. G.,Britton, Benjamin,Peckham, Timothy J.,Metzler, Lukas,Holdcroft, Steven
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supporting information
p. 9058 - 9061
(2017/07/24)
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- C-Au Covalently Bonded Molecular Junctions Using Nonprotected Alkynyl Anchoring Groups
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We report on an approach to realize carbon-gold (C-Au) bonded molecular junctions without the need for an additive to deprotect the alkynyl carbon as endstanding anchor group. Using the mechanically controlled break junction (MCBJ) technique, we determine the most probable conductance value of a family of alkynyl terminated oligophenylenes (OPA(n)) connected to gold electrodes through such an akynyl moiety in ambient conditions. The molecules bind to the gold leads through an sp-hybridized carbon atom at each side. Comparing our results with other families of molecules that present organometallic C-Au bonds, we conclude that the conductance of molecules contacted via an sp-hybridized carbon atom is lower than the ones using sp3 hybridization due to strong differences in the coupling of the conducting orbitals with the gold leads.
- Olavarria-Contreras, Ignacio José,Perrin, Mickael L.,Chen, Zhi,Klyatskaya, Svetlana,Ruben, Mario,Van Der Zant, Herre S. J.
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supporting information
p. 8465 - 8469
(2016/07/26)
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- Pyrazine-based donor tectons: Synthesis, self-assembly and characterization
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Two new supramolecular building blocks derived from pyrazine are introduced. These molecules, having pendant pyridine units covalently linked to central pyrazine ring, are structurally rigid with pre-defined bite angles. Therefore they can act as donor tectons in design of supramolecular hexagons using coordination driven self-assembly protocol. Multinuclear NMR (including 1H DOSY) and mass spectrometry have been utilized to confirm the purity and stoichiometry of these self assembled hexagonal ensembles. PM6 molecular modeling studies corroborate their hexagonal shape and nanoscalar dimensions.
- Bhowmick, Sourav,Chakraborty, Sourav,Marri, Subba R.,Behera,Das, Neeladri
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p. 8992 - 9001
(2016/02/05)
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- Highly Luminescent Microporous Organic Polymer with Lewis Acidic Boron Sites on the Pore Surface: Ratiometric Sensing and Capture of F- Ions
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Reversible and selective capture/detection of F- ions in water is of the utmost importance, as excess intake leads to adverse effects on human health. Highly robust Lewis acidic luminescent porous organic materials have potential for efficient
- Suresh, Venkata M.,Bandyopadhyay, Arkamita,Roy, Syamantak,Pati, Swapan K.,Maji, Tapas Kumar
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p. 10799 - 10804
(2015/07/20)
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- Tris(trifluoromethyl)germylethynyl derivatives of biphenyl and anthracene: Synthesis, structure, and evidence of the intramolecular charge transfer on the germanium center
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Symmetrical and unsymmetrical 4,4′-biphenyl, and 9,10-anthracene derivatives with tris(trifluoromethyl)germylethynyl -CC-Ge(CF3)3 substitutes have been prepared, their properties have been studied and compared with those of dimethyl(
- Ermolaev, Nikolai L.,Lenin, Ilya V.,Fukin, Georgii K.,Shavyrin, Andrei S.,Lopatin, Mikhail A.,Kuznetsova, Olga V.,Andreev, Boris A.,Kryzhkov, Denis I.,Ignatov, Stanislav K.,Chuhmanov, Evgeny P.,Berberova, Nadezhda T.,Pashchenko, Konstantin P.
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- Aggregation-induced emission of tetraphenylethene-hexaphenylbenzene adducts: Effects of twisting amplitude and steric hindrance on light emission of nonplanar fluorogens
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A series of nonplanar tetraphenylethene (TPE)-hexaphenylbenzene (HPB) adducts was designed and synthesized by Diels-Alder reaction of the acetylene precursors and tetraphenylcyclopentadienone. All of the adducts showed aggregation-induced emission features. The twisting amplitude and steric hindrance of the TPE and HPB units were found to play a crucial role in their fluorescence behaviors in the aggregated state. Nonplanar fluorogens: A series of nonplanar tetraphenylethene and hexaphenylbenzene adducts was designed and synthesized (see scheme) to study the aggregation-induced emission process. The twisting amplitude and steric effect of the units were found to be crucial in the fluorescence behavior of the luminogens.
- Hu, Rongrong,Lam, Jacky W. Y.,Liu, Yi,Zhang, Xiaoa,Tang, Ben Zhong
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p. 5617 - 5624
(2013/06/26)
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- Catenane gel: Synthesis of high molecular weight poly[2]catenanes by Sonogashira coupling polymerization
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A first catenane polymer gel was obtained by Sonogashira coupling reaction of diiodo[2]catenane and 4,4′-diethynylbiphenyl. Because of the linearity and rigidity of the ethynylene group formed in the coupling reaction, the formation of undesired cyclic dimer was inhibited, and a very high molecular weight (Mn > 2.3 × 105) poly[2]catenane was synthesized. The polymer was gelated without any chemical cross-linkage and swelled in DMF.
- Hagiwara, Toshiki,Murano, Yasuhiro,Watanabe, Yuki,Hoshi, Toru,Sawaguchi, Takashi
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supporting information; experimental part
p. 2805 - 2808
(2012/07/27)
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- Microporous polyphenylenes with tunable pore size for hydrogen storage
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A series of highly porous polymers with similar BET surface areas of higher than 1000 m2 g-1 but tunable pore ranging from 0.7 nm to 0.9 nm were synthesized through facile ethynyl trimerization reaction to demonstrate the surface pro
- Yuan, Shengwen,Dorney, Brian,White, Desiree,Kirklin, Scott,Zapol, Peter,Yu, Luping,Liu, Di-Jia
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supporting information; experimental part
p. 4547 - 4549
(2010/10/21)
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- Rigid rod and tetrahedral hybrid compounds featuring nucleobase and nucleoside End-capped structures
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Being aimed at a new type of porous solids, a moduled design strategy of molecular tectons, making use of the conjugation between a shape defined artificial backbone and the bioinspired molecular fragments of nucleobases or nucleobase derivatives as functional end-caps, has been developed. This led to the formation of the new hybrid compounds 1-13 of linear and tetrahedral geometry, containing uracil, adenine, adenosine, guanosine and its acylated analogs as the sticky end-cap sites. The compounds were synthesized from a halogen or ethynyl substituted nucleobase component and the corresponding ethynylated spacer unit following a metal assisted coupling process as the key reaction step. X-Ray crystal structure analysis demonstrates that the parent compound 1 is a solvent complex with DMSO (1:2), showing the DMSO molecules incorporated in a hydrogen bonded layer structure. Specific dependencies of the fluorescence properties of the new compounds in solution on the structure of the molecules are reported. A selection of solid compounds has been studied in respect of their ability to adsorb organic vapours. They revealed significant differences both in the sorption capacity and the selectivity towards particular solvent vapours.
- Schindler, Diana,Eissmann, Frank,Weber, Edwin
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experimental part
p. 3549 - 3560
(2010/01/06)
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- A joint experimental and computational study on the electronic communication in diethynylaryl-bridged (η5-C5H 5)Fe(η2-dppe) and (η5-C 5H5)-Fe(CO)2 units
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A family of bimetallic complexes [Cp(CO)2Fe-C≡C-Ar- C≡C-Fe(CO)2Cp] {Cp = C5H5; 6a-g: Ar = C4H2S (a), 3-(C4H9)-C4HS (b), 3-(C16H33)-C4HS (c), C6H 4 (d), 2,5-bis-(OC4H9)-C6H 2 (e), 2,5-bis(OC8H17)-C6H 2 (f), (C6H4)2 (g)} was prepared by the three-step Pd-catalysed extended one-pot (EOP) synthetic protocol from Bu3Sn-C≡CH, X-Ar-X (X = I, Br) and Cp(CO)2FeI. Complexes 6a,d,g were then exposed to ultraviolet irradiation in the presence of an equivalent amount of 1,2-bis(diphenylphosphanyl)ethane (dppe) to form the corresponding bimetallic complexes [Cp(dppe)Fe-C≡C-Ar-C≡C-Fe(dppe) Cp] (7a,d,g). Compounds 6a-g and 7a,d,g were characterised by cyclic voltammetry (CV). The most significant electrochemical information comes from the oxidation of the dppe derivatives. The ΔE° separations between the subsequent reversible waves suggest that the efficiency of the metal-metal electronic coupling decreases in the order 7a > 7d > 7g. Complexes 7a and 7g were also chemically oxidised with [Fe(Cp*]2[BF4] {Cp* = C5(CH3)5} and [Fe(Cp)] 2[BF4] respectively, and the near infrared (NIR) spectra of the mixed-valence species 7a+ and 7g+ were recorded. A strong intervalence transition (IT) band was observed only for the radical cation 7a+. While this finding confirms the existence of an electronic interaction between the two termini when a 2,5-thiophene group is present in the spacer, the NIR spectrum of 7g+ reveals a reduced efficiency in conveying electrons when the C4H2S moiety is replaced by a 4,4′-biphenyl. In order to rationalise and quantify the extent of electronic communication, ruled by geometrical and electronic factors, density functional computational results on selected [Cp (PH3) 2Fe] and [Cp(CO)2Fe] binuclear model complexes are reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Medei, Laura,Orian, Laura,Semeikin, Oleg V.,Peterleitner, Mikhail G.,Ustynyuk, Nikolai A.,Santi, Saverio,Durante, Christian,Ricci, Antonella,Lo Sterzo, Claudio
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p. 2582 - 2597
(2007/10/03)
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- Di-organoiron mixed valent complexes featuring "(η2- dppe)(η5-C5Me5)Fe" endgroups: Smooth class-III to class-II transition induced by successive insertion of 1,4-phenylene units in a butadiyne-diyl bridge
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The synthesis and study of a new redox family of symmetric dinuclear iron(II/III) complexes featuring "(η2-dppe) (η5-C5Me5)Fe(C≡C)" endgroups connected by a bis(diethynyl)-4,4′-biphenyl spacer are reported. The solid-state structures were determined (X-rays) for the homovalent Fe(II)/Fe(II) and Fe(III)/Fe(III) parents. In contrast, the mixed valent (MV) complex 5[PF6] has a low thermodynamic stability (Kc around 10) and cannot be isolated in a pure form, but was studied in solution. According to the Robin and Day classification, it constitutes a remarkable example of well-behaved weakly coupled class-II organometallic MV compound. The photodriven metal-metal electron-transfer process takes place over ca. 16 A and corresponds to an electronic coupling of ca. 150 cm-1 with a reorganization energy of ca. 6250 cm-1 in dichloromethane. A similar investigation was also conducted in the near-IR range for the known and much more stable MV analogue 3[PF6] featuring the 1,4-phenyl unit instead of the 4,4′-biphenyl one (Kc = 2.6 104). The latter also exhibits a localized valency, but presents a very intense intervalence charge-transfer band (IVCT) with a cutoff on the low-energy side. A much stronger electronic coupling is derived (ca. 1700 cm-1) from the band shape for this MV complex in the frame of the two-level model. Although slowed, the electron exchange is not disrupted by insertion of an additional para-phenylene moiety into a 1,4-diethynylaryl bridge. Thus, starting from a compound with a butadiyne-diyl spacer, stepwise paraphenylene insertions in the bridge produce a smooth Class-III to Class-II transition for the corresponding MV complexes.
- Ghazala, Safaa Ibn,Paul, Frederic,Toupet, Loic,Roisnel, Thierry,Hapiot, Philippe,Lapinte, Claude
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p. 2463 - 2476
(2007/10/03)
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- Reduced fluorescence quenching of cyclodextrin-acetylene dye rotaxanes
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An acetylene dye rotaxane with α-CD has been synthesized using the Heck-Cassar-Sonogashira-Hagihara-type reaction in aqueous solution. Free dye with tetracarboxylic acids is found to be highly sensitive to various metal ions, showing high Stern-Volmer con
- Park, Jong S.,Wilson, James N.,Hardcastle, Kenneth I.,Bunz, Uwe H. F.,Srinivasarao, Mohan
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p. 7714 - 7715
(2007/10/03)
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- Syntheses, optical and electrochemical properties of 4,4′-bis-[2-(3, 4-dibutyl-2-thienylethynyl)]biphenyl and its oligomers
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New π-conjugated oligomers (1-3) combined of thiophene rings, CC units, and phenylene rings were synthesized. The monomer (1) was synthesized by Sonogashira cross-coupling reaction. Lithiation and oxidation of the monomer led to the formation of dimer (2) and trimer (3). Optical and electrochemical properties of compounds 1-3 were studied. The oligomers with thioacetyl moieties were synthesized for self-assembly.
- Liu, Lei,Liu, Zhanxiang,Xu, Wei,Xu, Hai,Zhang, Deqing,Zhu, Daoben
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p. 3813 - 3817
(2007/10/03)
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- Investigation of two-photon absorption behavior in symmetrical acceptor-π-acceptor derivatives with dimesitylboryl end-groups. Evidence of new engineering routes for TPA/transparency trade-off optimization
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Investigations of the non-linear optical properties of a novel series of A-π-A quadrupoles, based on dimesitylboron end-groups, reveal the promising potential of elongated vinylboranes derivatives for combined enhanced two-photon absorption cross-section and improved transparency in the visible region. In addition, the excited state lifetime can be significantly enhanced in A-π-A′-π-A derivatives. This opens a new route towards optimized molecules for optical power limiting. The Owner Societies 2005.
- Chariot, Marina,Porres, Laurent,Entwistle, Christopher D.,Beeby, Andrew,Marder, Todd B.,Blanchard-Desce, Mireille
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p. 600 - 606
(2007/10/03)
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- Cytotoxicity of 2,2':6',2-terpyridineplatinum(II) complexes against human ovarian carcinoma
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2,2':6',2''-Terpyridineplatinum(II) complexes are shown to possess cytotoxicity against a number of human ovarian tumor cell lines. Many of the complexes show similar activity against cisplatin- and doxorubicin-resistant cell lines as the parental cells suggesting that there is little or no cross- resistance with cisplatin or doxorubicin. The cytotoxicity of bis[2,2':6',2''-terpyridineplatinum(II)] complexes is strongly dependent on the nature of the linker. Bis[2,2': 6',2-terpyridineplatinum(II)] complexes with a flexible linker at the 4'-position show poor cytotoxicity; by contrast bis[2,2':6',2-terpyridineplatinum(II)] complexes with rigid and short linkers at platinum(II) are strikingly effective. Several of the compounds show greater cytotoxicity against human ovarian cell lines than carboplatin, the therapeutic agent currently advocated for the treatment of human ovarian cancers.
- Lowe, Gordon,Droz, Anne Sophie,Vilaivan, Tirayut,Weaver, George W.,Park, Jenny J.,Pratt, Jonathan M.,Tweedale, Lindsay,Kelland, Lloyd R.
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p. 3167 - 3174
(2007/10/03)
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- The design and synthesis of bis-[4'-azido-2,2':6',2-terpyridine platinum(II)] complexes with rigid and extended linkers for studying the topology of DNA by photoaffinity labeling
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A family of bis-[4'-Azido-2,2':6',2''-terpyridine platinum(II)] complexes with linear linkers of varying length have been synthesized. They have been designed to bis-intercalate into two DNA duplexes in close proximity, the azido groups allowing the sites of intercalation to be photoaffinity labeled. The linker to Pt(II) bonds are susceptible to cleavage by thiols and cyanide ion, which is a requirement for the intended method of analysis by 2D gel electrophoresis. (C) 1999 Academic Press.
- Lowe, Gordon,Droz, Anne-Sophie,Park, Jenny J.,Weaver, George W.
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p. 477 - 486
(2007/10/03)
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- The 'Inverse Electron-demand' Diels-Ader Reaction in Polymer Synthesis. Part 1. A Convenient Synthetic Route to Diethynyl Aromatic Compounds
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The simple procedure whereby acetophenone derivatives are converted, by reaction with phosphoryl chloride and N,N-dimethylformamide, into β-chlorocinnamaldehydes, and thence, by base-induced elimination, into ethynylarenes, has been extended to diketones of the type MeCOC6H4COMe (m- and p-) and (p-MeCOC6H4)2X (X = O, S, SO2, CH2, CO, or a single bond): the corresponding diethynyl compounds are obtained by this route in acceptable yield. 1,3,5-Triacetylbenzene is similarly converted into 1,3,5-triethynylbenzene.
- Royles, Brodyck J. L.,Smith, David M.
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p. 355 - 358
(2007/10/02)
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