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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, a single crystal X-ray diffraction study and 1H NMR spectroscopy have confirmed that 1,4,7-trithiacycloundec -9-yne adopts an exodentate conformation in the solid and solution states.

14 citations

Journal ArticleDOI
TL;DR: The synthesis of a selection of benzo-fused NBD derivatives that contain an aromatic unit, benzene, naphthalene or phenanthrene, fused to one of the NBD double bonds, while the carbon atoms of the other double bond are functionalized with donor and acceptor groups to increase the energy difference between the two isomers.
Abstract: The photochromic norbornadiene/quadricyclane (NBD/QC) couple has found interest as a molecular solar thermal energy (MOST) system for storage of solar energy. To increase the energy difference between the two isomers, we present here the synthesis of a selection of benzo-fused NBD derivatives that contain an aromatic unit, benzene, naphthalene or phenanthrene, fused to one of the NBD double bonds, while the carbon atoms of the other double bond are functionalized with donor and acceptor groups. The synthesis protocols involve functionalization of benzo-fused NBDs with bromo/chloro substituents followed by a subjection of these intermediates to a cyanation reaction (introducing a cyano acceptor group) followed by a Sonogashira coupling (introducing an arylethynyl donor group, -CCC6H4NMe2 or -CCC6H4OMe). While the derivatives have good absorption properties in the visible region (redshifted relative to parent system) in the context of MOST applications, they lack the ability to undergo NBD-to-QC photoisomerization, even in the presence of a photosensitizer. It seems that loss of aromaticity of the fused aromatics is too significant to allow photoisomerization to occur. The concept of destroying aromaticity of a neighboring moiety as a way to enhance the energy density of the NBD/QC couple thus needs further structural modifications, in the quest for optimum MOST systems.

14 citations

Journal ArticleDOI
TL;DR: In this article, the origin of double bond pyramidalization in the series of norbornene and norbornadiene derivatives and the effect of heteroatoms on the magnitude of the double bond bending are reported.

14 citations

Journal ArticleDOI
TL;DR: In this article, a number of lithium alkynylcuprates, generated in situ from the corresponding lithium acetylides and copper(I) cyanide, were used to give the respective enediynes 2 in moderate to good isolated fields.
Abstract: BicycloalkenyIdiiodonium salts, di[phenyl(trifluoromethanesulfonyloxy)iodo]norbornadiene (1a) and di[phenyl(trifluoromethanesulfonyloxy)iodo]-3,5-epoxy-1,4-cyclohexadiene (1b) react under mild conditions, with a number of lithium alkynylcuprates, generated in situ from the corresponding lithium acetylides and copper(I) cyanide, to give the respective enediynes 2 in moderate to good isolated fields

14 citations

Journal ArticleDOI
TL;DR: In this paper, a block copolymer of poly(5-ethynyl-2,2′-bipyridine) was obtained by the addition of 1 to a poly(phenylacetylene) containing a living end.
Abstract: 5-Ethynyl-2,2′-bipyridine (1; bpyC≡CH) polymerized in the presence of catalytic amounts of [RhF(COD)(PPh3)] or [Rh(μ-OH)(COD)]2 (COD = 1,5-cyclooctadiene) in 74–91% yields. In contrast, [Rh(μ-X)(NBD)]2 (X = Cl or OMe; NBD = norbornadiene) did not catalyze the polymerization of 1 or gave low yields of the polymer. The obtained polymer, poly(5-ethynyl-2,2′-bipyridine) [2; (bpyCCH)n], was highly stereoregular with a predominant cis–transoidal geometry. Random copolyacetylenes containing the 2,2′-bipyridyl group with improved solubility in organic solvents were obtained by the treatment of a mixture of 1 and phenylacetylene (3) or 1-ethynyl-4-n-pentyl-benzene with catalytic amounts of [RhF(COD)(PPh3)]. A block copolymer of 1 and 3 was prepared by the addition of 1 to a poly(phenylacetylene) containing a living end. The reaction of 2 with [Mo(CO)6] produced an insoluble polymer containing [Mo(CO)4(bpy)] groups, whereas with [RuCl2(bpy)2] or [Ru(bpy)2(CH3COCH3)2](CF3SO3)2, it gave soluble metal–polymer complexes containing [Ru(bpy)3]2+ groups. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43:3167–3177, 2005

14 citations


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