278-06-8

Usage

Uses

Used in Chemical Synthesis:
Quadricyclane is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows for a wide range of chemical reactions, making it a valuable building block in the development of new molecules and materials.
Used in Research and Development:
Due to its unique structure and properties, quadricyclane is often used in research and development to study the effects of strain and bond coupling in organic molecules. It serves as a model compound for understanding the behavior of other bridged norbornane derivatives and their potential applications.
Used in Pharmaceutical Industry:
Quadricyclane has potential applications in the pharmaceutical industry as a starting material for the synthesis of various drug candidates. Its unique structure and reactivity make it an attractive candidate for the development of novel therapeutic agents.
Used in Material Science:
Quadricyclane's unique structure and properties make it a candidate for use in the development of new materials with specific properties, such as high thermal stability or unique mechanical characteristics. Researchers are exploring its potential applications in the creation of advanced materials for various industries.

InChI:InChI=1/C7H8/c1-2-4-5(2)7-3(1)6(4)7/h2-7H,1H2

Upstream product

• 23979-29-5 exo-3,4-diazotricyclo[4.2.1.0^2,5]nona-3,7-diene 
• 74-89-5 methylamine 
• 177552-58-8 quadricyclane anion 
• 177552-59-9 2-quadricyclanide anion 
• 71-43-2 benzene 
• 16104-45-3 3,4-diazaquadricyclo[6.1.0.0^2,60^5,9]non-3-ene 
• 67-56-1 methanol 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 1755-01-7 endo-Dicyclopentadien 
• 205518-36-1 1,6-dibromoquadricyclane 
• 205518-40-7 1,6-dilithiotetracyclo[3.2.0.0^2,7.0^4,6]heptane 
• 96227-99-5 4,5-diazatricyclo<4.3.0.0^3,7>nona-4,8-diene 
• 39521-78-3 syn-Tricyclo<3.2.0.0^2,4>hept-6-en 

Downstream Products

• 88074-02-6 N-[(1R,3S,4R,5S)-5-(2-Nitro-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]hept-3-yl]-acetamide 
• 88074-02-6 N-[(1R,3R,4R,5S)-5-(2-Nitro-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]hept-3-yl]-acetamide 
• 85684-71-5 Acetic acid (1R,2R,4S,5S,6S)-6-chloro-5-(4-chloro-phenylsulfanyl)-bicyclo[2.2.1]hept-2-yl ester 
• 85684-70-4 Acetic acid (1R,2R,4S,5R,6R)-5-chloro-6-(4-chloro-phenylsulfanyl)-bicyclo[2.2.1]hept-2-yl ester 
• 74-89-5 methylamine 
• 177552-58-8 quadricyclane anion 
• 177552-59-9 2-quadricyclanide anion 
• 71-43-2 benzene 
• 21516-65-4 3-methoxynortricyclene 
• 17190-87-3 5-exo-methoxybicyclo[2.2.1]hept-2-ene 
• 86-53-3 1-Cyanonaphthalene 
• 2890-98-4 exo-5-norbornen-2-ol 
• 658074-45-4 exo-4,4-difluoro-3-oxa-tricyclo[4.2.1.0^2,5]non-7-ene 

Relevant academic research and scientific papers

Photocalorimetry. 6. Enthalpies of Isomerization of Norbornadiene and of Substituted Norbornadienes to Corresponding Quadricyclenes

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 solar-energy-derived strained hydrocarbon as an energetic hypergolic fuel

Quadricyclane (QC), synthesized from photoisomerization and commonly used for solar-energy conversion and storage, is found to be an excellent hypergolic fuel. The ignition delay time of QC-N2O4 is 29 ms, which is decreased to 18 ms by addition of boron nanoparticles. Importantly, quadricyclane has 18.9% higher specific impulsion than currently used but dangerous dimethylhydrazine. This journal is

A Silica-supported Inorganic Photosensitizer

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.

Mechanistic Approach to the Sensitization Process of Aromatic Ketones in the Isomerization between Norbornadiene and Quadricyclane

The quantum yields for norbornadiene(N)-->quadricyclane(Q) and Q-->N isomerization were determined in acetonitrile using several substituted benzophenones (BPs) as triplet sensitizers.For the N-->Q isomerization, BPs with electron-donating substituents exhibited higher quantum efficiency (0.4-0.6) than BPs with electron-accepting substituents.The quantum yields for Q-->N isomerization increased with electron-accepting ability of the substituents on BPs, but were lower than 0.1.The rate constants for quenching of triplet BPs by N and Q were also determined in acetonitrile by means of laser flash photolysis.The rate constants for N were not dependent on the triplet energies (ET) of BPs but dependent on electronic properties of the substituents on BPs.On the contrary, those for Q increased with decreasing ET of BPs and with increasing Hammet's ? constants of the substituents of BPs.Based on these observations an addition-elimination process is proposed for the N-->Q isomerization, and electron transfer process for the Q-->N isomerization.

Synthesis of Annelated Oxetans via Cycloaddition Reactions of Quadricyclane under Thermal and High Pressure Conditions

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)

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.

PHOTOISOMERIZATION OF 7-SUBSTITUTED NORBORNADIENE-CYCLODEXTRIN INCLUSION COMPLEXES

The photoisomerization of 7-substituted norbornadiene-cyclodextrin inclusion complexes, in which the substituents are t-butoxyl, acetoxyl, and hydroxyl groups, gave 7-substituted quadricyclene-cyclodextrin inclusion complexes.

Possibility of Photochemical Energy Storage in the Norbornadiene - Quadricyclane System. Part II

Sensitization effect of an organic sensitizer propiophenone in the photoisomeric system norbornadiene - quadricyclane was investigated.Experimental data on the N - Q conversion for various concentrations of the sensitizer and irradiation times were given.Results confirmed a proposed kinetic model.

Reactions of quadricyclane with fluorinated nitrogen-containing compounds. Synthesis of 3-aza-4-perfluoroalkyl-tricyclo[4.2.1.02,5]non-3,7- dienes

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.

Photosensitized Isomerization of Norbornadiene to Quadricyclane with (Arylphosphine)copper(I) Halides

The (arylphosphine)copper(I) halides were studied as sensitizers in the photoisomerization side of a solar energy storage cycle based on the interconversion of norbornadiene (NBD) and quadricyclane (Q).The lowest electronic excited state of these compounds can be effective triplet energy sensitizers as evidenced by a maximum quantum yield of 1.0 with (MePh2P)3CuX.The efficiency of the (MePh2P)3CuX sensitizers is unprecedented compared to other reported inorganic complexes used as sensitizers for the NBD/Q system.The (MePh2P)3CuCl sensitizer has an intersystem crossing triplet yield of 1.0 with a triplet lifetime in benzene at room temperature of 3.3 μs.The triplet energy transfer rate constant with NBD is 8x107 M-1 s-1.While the L3CuX (L=Ph3P, MePh2P) species are the most efficient sensitizers in solution, dissociation of the ligand from the metal in dilute solution detracts from their otherwise attractive features.The much lower quantum efficiency observed for the (Ph3P)3CuX compared to the MePh2P sensitizer is attributed to this extensive ligand dissociation.The coordinately unsaturated (arylphosphine)copper(I) halides produced by ligand dissociation appear to have extremely short lifetimes while the free ligand undergoes photodecomposition.Ground-state complexation of NBD with the coordinately unsaturated (arylphosphine)copper(I) halides is shown to occur in the presence of a large excess of NBD.Photoexcitation of NBD-(MePh2P)CuCl (C1) and NBD-(MePh2P)2CuCl (C2) complexes can produce Q, but with quantum efficiencies less than one.