278-06-8Relevant articles and documents
Photocalorimetry. 6. Enthalpies of Isomerization of Norbornadiene and of Substituted Norbornadienes to Corresponding Quadricyclenes
Harel, Yaacov,Adamson, Arthur W.,Kutal, Charles,Grutsch, Paul A.,Yasufuku, Katsutoshi
, p. 901 - 904 (1987)
The enthalpies of isomerization of norbornadiene and of several substituted norbornadienes to the corresponding quadricyclenes have been determined by the method of photocalorimetry.This method also gives f, the percent of adsorbed light energy of a given wavelength that is stored chemically as a consequence of the photoinduced isomerization.The results for 25 deg C are as follows (compound, solvent, ΔH in kcal mol-1, fwavelength, nm): norbornadiene, cyclohexane, 14.0 +/- 1, f313 = 15.0 +/- 1percent: 2,3-bis(carbomethoxy)norbornadiene, acetonitrile, 25.2 +/- 3.5, f313 = 12.4 +/- 2.2percent; 2,3-dicyanonorbornadiene, acetonitrile, 22.0 +/- 2.3, f313 = 11.2 +/- 1.9percent; 1,2,3-trimethyl-5,6-dicyanonorbornadiene, acetonitrile, 21.0 +/- 2.0, f366 = 15.5 +/- 1.7percent.The position of the first absorption band shifts progressively to longer wavelengths in the above sequence, and the results show that such shifting toward the solar insolation region does not impair the energy storage ability of the system.For the parent, norbornadine system, it was necessary to use acetophenone as sensitizer, and it is possible that minor secondary photolysis effects led to the relatively low ΔH value; the value has the merit that it is the practical one for conditions relevant to actual solar energy storage.
A Silica-supported Inorganic Photosensitizer
Grutsch, Paul A.,Kutal, Charles
, p. 893 - 894 (1982)
Adsorption of 2+ (bipy = 2,2'-bipyridine) onto silica gel does not adversely affect the efficiency with which this transition metal complex photosensitizes the valence isomerization of norbornadiene to quadricyclene.
Transition metal photoassisted valence isomerization of norbornadiene. An attractive energy-storage reaction
Schwendiman, Dwight P.,Kutal, Charles
, p. 719 - 721 (1977)
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Synthesis of Annelated Oxetans via Cycloaddition Reactions of Quadricyclane under Thermal and High Pressure Conditions
Papadopoulos, Mihalis,Jost, Roland,Jenner, Gerard
, p. 221 - 222 (1983)
Annelated oxetans are synthesized via thermal or pressure assisted cycloaddition of quadricyclane with the appropriate carbonyl bond activated by electron withdrawing groups; the new compounds are very stable and do not undergo the usual cycloreversion of four membered rings.
Synthesis and gas-separation properties of metathesis poly(3-fluoro-3-pentafluoroethyl-4,4-bis(trifluoromethyl)tricyclonene-7)
Bermeshev,Starannikova,Sterlin,Tyutyunov,Tavtorkin,Yampolskii, Yu. P.,Finkelshtein, E. Sh.
, p. 753 - 758 (2015)
Metathesis polymerization of 3-fluoro-3-pentafluoroethyl-4,4-bis(trifluoromethyl)tricyclononene-7 (F-PTCN) and the properties of the resulting polymer, particularly gas permeability, have been studied. It has been found that F-PTCN exhibits high thermal stability. The gas separation parameters of the material (P(O2) = 60 Barrer, P(CO2) = 240 Barrer) are close to those of fluorinated polynorbornenes studied previously. The newly synthesized fluorinated metathesis polytricyclononene has a lower gas permeability than metathesis polytricyclononene bearing two Me3Si groups in the monomer unit, but it is significantly superior to the latter in gas separation selectivity for some gas pairs.
Manassen
, p. 38,40 (1970)
Van Ingen et al.
, p. 3665,3667 (1970)
Reactions of quadricyclane with fluorinated nitrogen-containing compounds. Synthesis of 3-aza-4-perfluoroalkyl-tricyclo[4.2.1.02,5]non-3,7- dienes
Petrov, Viacheslav A.,Davidson, Frederic,Marshall, Will
, p. 1621 - 1628 (2004)
The cycloaddition reactions of quadricyclane (1) and polyfluorinated imines and nitriles were studied. Both (CF3)2CNH and (CF 3)2CN(2-FC6H4) were found to have low reactivity towards 1, giving the corresponding [2 + 2 + 2] cycloadducts in a low yield. C2F5NCFCF3 however, reacts with 1 rapidly, giving a mixture of two isomeric cycloadducts in a high yield. Perfluoroalkyl nitriles RfCN (Rf = CF3, C 2F5, n-C3F7) were found to have surprisingly high reactivity to 1 producing exo-3-aza-4-(fluoroalkyl)- tricyclo[4.2.1.02,5]non-3,7-dienes in 56-81% yields at elevated temperature. Exo-3-aza-4-(perfluoroalkyl)-tricyclo[4.2.1.02,5]non-3, 7-dienes rapidly react with CF3Si(CH3)3 in the presence of CsF catalyst. The reaction results in addition of CF 3Si(CH3)3 across the CN bond of the azadienes with selective formation of only one stereoisomer of exo-3-aza-3- (trimethylsilyl)-4,4-bis(perfluoroalkyl)-tricyclo[4.2.1.02,5]non-7- enes. Silyl group in this compounds can be removed either by the action of tetrabutylammonium fluoride hydrate, leading to the formation of the corresponding amine after hydrolysis, or by reaction with HCl resulting in the formation of the corresponding amine hydrochloride. The reaction of quadricyclane with perfluoroazaalkenes and perfluorinated nitriles leads to high yield formation of the corresponding cycloadducts.
Macroscopic Diffusion Control in High-Pressure Photochemistry
Tamura, Katsuhiro,Sugiyama, Sigeru,Noble, W. J. le
, p. 3836 - 3837 (1984)
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Dauben,Cargill
, p. 197,200 (1961)
Tabushi et al.
, p. 787 (1972)
Energy storage material based on 2,5-norbornadiene derivative and preparation method thereof
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Page/Page column 9, (2018/12/13)
The invention discloses an energy storage material based on a 2,5-norbornadiene derivative and a preparation method thereof. An esterification method is used for preparing an ortho grafted bisazo benzene 2,5-norbornadiene derivative; two azobenzene groups are introduced at 2,5-norbornadiene in an ortho manner, so that norbornadiene is obviously subjected to Einstein shift; the photon yield is effectively improved. 2,5-norbornadiene and the azobenzene groups are combined, so that the heat storage energy density can be effectively improved; the storage energy is increased. The material has excellent optical performance and is hopeful to be applied in the fields of light and heat conversion and energy storage.
REDOX-AUXILIARY CATALYSIS
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Paragraph 0007; 0102, (2015/05/26)
Disclosed herein is a method of activating a compound for a chemical reaction comprising functionalizing a compound with a redox auxiliary group and oxidizing the redox auxiliary group that is bonded to the compound, thereby activating the compound, wherein the activated compound undergoes a chemical reaction to form a product and the oxidation of the redox auxiliary group is reversible. Methods of making and using these materials are also disclosed.
