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Norbornadiene

About: Norbornadiene is a research topic. Over the lifetime, 2389 publications have been published within this topic receiving 38603 citations.


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Journal ArticleDOI
TL;DR: In this paper, four chiral methylpropargyl esters bearing azobenzene groups were synthesized and polymerized with Rh+(nbd)[η6-C6H5B−- (C6h5)3] (nbd=norbornadiene) catalyst to give the corresponding polymers with moderate molecular weights (Mn=8.4×103−15.7×103) in good yields (76%? -?91%).
Abstract: Novel chiral methylpropargyl esters bearing azobenzene groups, namely, 4-[4′-(benzyloxy)phenylazophenyl]- carbonyl-(S)-1-methylpropargyl ester (e), 4-[4′-(n-butyloxy)phenylazophenyl]carbonyl-(S)-1-methylpropargyl ester (f), 4-[4′-(n-hexyloxy)phenylazophenyl]carbonyl-(S)-1-methylpropargyl ester (g), and 4-[4′-(n-octyloxy)phenylazo- phenyl]carbonyl-(S)-1-methylpropargyl ester (h) were synthesized and polymerized with Rh+(nbd)[η6-C6H5B−- (C6H5)3] (nbd=norbornadiene) catalyst to give the corresponding polymers with moderate molecular weights (Mn=8.4×103–15.7×103) in good yields (76%? –?91%). The structures of polymers were illustrated by IR and NMR spectroscopies. Polymers were soluble in comment organic solvents including toluene, CHCl3 CH2Cl2, THF, and DMSO, while insoluble in diethyl ether, n-hexane and methanol. Large optical rotations of polymer solutions demonstrated that all the polymers take a helical structure with a predominantly one-handed screw sense in organic solvents.

2 citations

Journal ArticleDOI
25 Aug 2020
TL;DR: Three new phenylacetylene monomers having one or two carbamate groups were synthesized and polymerized by using (Rh(norbornadiene)Cl)2 as an initiator, with different solubility and membrane-forming abilities.
Abstract: Three new phenylacetylene monomers having one or two carbamate groups were synthesized and polymerized by using (Rh(norbornadiene)Cl)2 as an initiator. The resulting polymers had very high average molecular weights (Mw) of 1.4-4.8 × 106, with different solubility and membrane-forming abilities. The polymer having two carbamate groups and no hydroxy groups in the monomer unit showed the best solubility and membrane-forming ability among the three polymers. In addition, the oxygen permeability coefficient of the membrane was more than 135 times higher than that of a polymer having no carbamate groups and two hydroxy groups in the monomer unit with maintaining similar oxygen permselectivity. A better performance in membrane-forming ability and oxygen permeability may be caused by a more extended and flexible cis-transoid conformation and lower polarity. On the other hand, the other two new polymers having one carbamate group and two hydroxy groups in the monomer unit showed lower performances in membrane-forming abilities and oxygen permeabilities. It may be caused by a very tight cis-cisoid conformation, which was maintained by intramolecular hydrogen bonds.

2 citations

Reference EntryDOI
15 Mar 2012
TL;DR: Norbornadiene as discussed by the authors is a ligand used in metal catalysis and is highly flammable, avoid exposure to heat, flame, and spark, and store under an inert gas and refrigerate; avoid prolonged exposure to light.
Abstract: [121-46-0] C7H8 (MW 92.14) InChI = 1S/C7H8/c1-2-7-4-3-6(1)5-7/h1-4,6-7H,5H2 InChIKey = SJYNFBVQFBRSIB-UHFFFAOYSA-N (reagent used in a variety of cycloadditions, addition reactions, and as ligand in metal catalysis) Alternate Name: norbornadiene. Physical Data: mp −19.1 °C; bp 89 °C; 0.906 g cm−3. Solubility: most organic solvents. Form Supplied in: colorless liquid; widely available. Purification: purified by distillation from activated alumina. Handling, Storage, and Precautions: highly flammable, avoid exposure to heat, flame, and spark. Store under an inert gas and refrigerate; avoid prolonged exposure to light. Norbornadiene has mild oral and inhalation toxicity; it should be worked within a well-ventilated area. Toxicity, LD50 (oral, mouse) 3850 mg kg−1; LC50 (inhalation, rat, 8 h) 14 100 ppm. Incompatible with strong acids, strong bases, and strong oxidizing agents.

2 citations

Journal ArticleDOI
TL;DR: In this article, the fundamental processes within these hybrid molecules have been investigated and the linker unit of the NBD/QC moiety with the fullerene core is used as a tool to tune the properties of the resulting hybrid molecules.
Abstract: With respect to molecular switches, initializing the quadricyclane (QC) to norbornadiene (NBD) back-reaction by light is highly desirable. Our previous publication provided a unique solution for this purpose by utilizing covalently bound C60 . In this work, the fundamental processes within these hybrids has been investigated. Variation of the linker unit connecting the NBD/QC moiety with the fullerene core is used as a tool to tune the properties of the resulting hybrids. Utilizing the Prato reaction, two unprecedented NBD/QC - fullerene hybrids having a long-rigid and a short-rigid linker were synthesized. Molecular dynamics simulations revealed that this results in an average QC-C60 distance of up to 14.2 A. By comparing the NBD-QC switching of these derivatives with the already established one having a flexible linker, valuable mechanistic insights were gained. Most importantly, spatial convergence of the QC moiety and the fullerene core is inevitable for an efficient back-reaction.

2 citations

Journal ArticleDOI
TL;DR: In this paper, the basicity of the 0 atom in the formyl group in organometallic aldehydes increases in the series: (CO)3MnC5H4CHO < C5H5Fe < C4C7H7-2-CHO; in (Cp)Rh(η4-C 7H7H2-CHO) norbornadiene π-complexes, where Cp=C5Me < C 5H5
Abstract: 1. The increased electron-donating reactivity of the 0 atom in CpRh(η4-C7H7-2-COR) complexes, where Cp=η5-C5H5, η5-C5H4Me, and η5-C5Me5 and R=H, Me, has been characterized by IR spectroscopic investigation and by the formation of hydrogen bonding with 4-fluorophenol. 2. The basicity of the 0 atom in the formyl group in organometallic aldehydes increases in the series: (CO)3MnC5H4CHO < C5H5FeC5H4CHO < C5H5RhC7H7-2-CHO; in (Cp)Rh(η4-C7H7-2-CHO) norbornadiene π-complexes the basicity of the formyl 0 atom increases as the donating ability of the Cp ligand increases, in the series Cp=C5H5 < C5Me < C5Me5. 3. The CpRhC7H7-2 group acts as a substituent with a strongly positive inductive effect as well as with a resonance effect of the same sign.

2 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202316
202240
202133
202040
201930
201829