1090-13-7Relevant articles and documents
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Roitt,Waters
, p. 3060 (1949)
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Martin
, p. 620,624 (1947)
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Ortho-quinodimethane from anthracene epidioxide: Scope of the Diels-Alder reaction and mild preparation of naphthalene derivatives
Siret, Bernard,Albrecht, Sébastien,Defoin, Albert
, p. 1075 - 1079 (2014)
The thermal isomerisation of anthracene epidioxide 3 has been known to give phenylenedioxy-ortho-quinodimethane 5 as a reactive transient. We presented herein the scope of the Diels-Alder reaction of this transient 5 with some dienophiles. In addition, a mild synthesis of naphthalene derivatives has been developed via base-induced cleavage of the obtained Diels-Alder adducts.
A Dynamic Tetracationic Macrocycle Exhibiting Photoswitchable Molecular Encapsulation
Wu, Huang,Chen, Yong,Zhang, Long,Anamimoghadam, Ommid,Shen, Dengke,Liu, Zhichang,Cai, Kang,Pezzato, Cristian,Stern, Charlotte L.,Liu, Yu,Stoddart, J. Fraser
, p. 1280 - 1289 (2019)
Designing macrocycles with appropriate molecular recognition features that allow for the integration of suitable external stimuli to control host-guest processes is a challenging endeavor which enables molecular containers to solubilize, stabilize, and separate chemical entities in an externally controllable manner. Herein, we introduce photo- and thermal-responsive elements into a semi-rigid tetracationic cyclophane, OPVEx2Box4+, that is composed of oligo(p-phenylenevinylene) pyridinium units and the biphenylene-bridged 4,4-bipyridinium extended viologens and adopts a rectangle-like geometry. It transpires that when the photoactive oligo(p-phenylenevinylene) pyridinium unit is incorporated in a macrocyclic scaffold, its reversibility is dramatically improved, and the configurations of the cyclophane can go back and forth between (EE)- and (EZ)-isomers upon alternating blue light irradiation and heating. When the macrocycle is found in its (EE)-configuration, it is capable of binding various π-electron-rich guests - e.g., anthracene and perylene - as well as π-electron-deficient guests - e.g., 9,10-anthraquinone and 5,12-tetracenequinone - through charge-transfer and van der Waals interactions. When irradiated with blue light, the (EE)-isomer of the cyclophane can be transformed successfully to the (EZ)-isomer, resulting in the switching off of the binding affinity for guest molecules, which are bound once again upon heating. The use of light and heat as external stimuli to control host-guest interactions involving a multi-responsive host and various guests provides us with a new opportunity to design and construct more-advanced molecular switches and machines.
Electron Acceptors Based on Cyclopentannulated Tetracenes
Kulkarni, Gajanan C.,Morales-Cruz, Jean L.,Hussain, Waseem A.,Garvey, Ian J.,Plunkett, Kyle N.
, p. 2572 - 2576 (2018)
New cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs) based on tetracene have been prepared by a palladium-catalyzed cyclopentannulation reaction. The new compounds have low-energy lowest unoccupied molecular orbitals (LUMOs) and relatively small band gaps. The photooxidative stability was intermediate to previously prepared CP-PAHs based on anthracene and pentacene as found in traditional acene stabilities. Scholl cyclodehydrogenation of pendant aryl groups led to materials that quickly formed endoperoxide products.
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Cava et al.
, p. 6458 (1959)
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Studies on the syntheses of tetracycline derivatives. III. Synthetic approach to adriamycin. Synthesis of the linear tetracyclic skeleton having the same BC ring system with adriamycin
Kametani,Chihiro,Takeshita,et al.
, p. 3820 - 3824 (1978)
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Studies on the syntheses of tetracycline derivatives. I. Thermolytic cycloaddition of o quinodimethanes with naphthoquinone
Kametani,Takahashi,Kajiwara,Hirai,Otsuka
, p. 2159 - 2163 (1974)
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Synthesis method of anthraquinone derivatives and tetracenedione derivatives through benzannulation reaction
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Paragraph 0029-0030; 0061; 0071, (2017/08/09)
The present invention relates to a method for synthesizing anthraquinone derivatives and tetracene dione derivatives through a benzannulation reaction, which presents a novel synthesis method, capable of processing synthesis easily, conveniently, and efficiently under mild conditions by an organic catalyst. The synthesis method uses an L-proline catalyst which is nontoxic, economical and easily available, compared to conventional production methods, thereby providing the anthraquinone derivatives and the tetracene dione derivatives through the one-pot benzannulation reaction of an α, β-unsaturated aldehyde compound, various 1,4-naphthoquinone compounds or 1,4-anthracenedione compounds. Various forms of anthraquinone derivatives or tetracene dione derivatives prepared by the synthesis method can be widely used for synthesis of natural products, dyes, and pharmaceutical products.COPYRIGHT KIPO 2017
