Layered Compounds. LII. Syntheses of Eleven Anthracenophanes

Iwama, A.; Toyoda, T.; Yoshida, Masatoshi; Otsubo, Tetsuo; Sakata, Yoshiteru; Misumi, Soichi

doi:10.1246/bcsj.51.2988

Cited by 40 publications

(13 citation statements)

References 15 publications

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“…Since the uv spectra of the fluorinated and non-fluorinated anthracenophanes do not differ significantly, it is expected that the hydrocarbon system analogous to 2 [8][9][10] should exhibit analogous photodimerization reactivity. Future work will also involve examination of the photochemistry of the two naphthalenophanes, 4 and 5, to see if analogous photodimerization processes may be observed for these two systems when using uv light.…”

Section: Resultsmentioning

confidence: 99%

An unprecedented photodimerization of an anthraceno[2.2]paracyclophane

Zhai¹,

Battiste²,

Abboud³

et al. 2005

Arkivoc

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Dedicated to our friend and colleague, Jim Coxon, on the occasion of his 65 th birthday Abstract Octafluoro[2.2](1,4)anthraceno-paracyclophane slowly undergoes a clean photodimerization upon being exposed, in solution, to fluorescent light. X-ray crystal analysis of this photodimer indicated that the aromaticity of the anthracene ring directly involved in the paracyclophane system was observed to be destroyed by forming a cyclobutane ring, with the two molecules linked to each other in a head to tail fashion.

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Section: Resultsmentioning

confidence: 99%

An unprecedented photodimerization of an anthraceno[2.2]paracyclophane

Zhai¹,

Battiste²,

Abboud³

et al. 2005

Arkivoc

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“…A photochemical reaction of this compound gave a cyclization product via a biradical intermediate. Two isomers of [2.2](1,4) anthracenophane, 6 and 7, were synthesized by Hofmann elimination [36,37]. Upon irradiation at 374 nm, syn isomer 7 readily gave [4+4]cycloaddition product 8 at the 9,10-positions and this photoproduct was reverted to 7 by heating or irradiation at 254 nm.…”

Section: Anthracenophanesmentioning

confidence: 99%

Three-Dimensional Aromatic Networks

Toyota

Iwanaga

2012

Topics in Current Chemistry

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Three-dimensional (3D) networks consisting of aromatic units and linkers are reviewed from various aspects. To understand principles for the construction of such compounds, we generalize the roles of building units, the synthetic approaches, and the classification of networks. As fundamental compounds, cyclophanes with large aromatic units and aromatic macrocycles with linear acetylene linkers are highlighted in terms of transannular interactions between aromatic units, conformational preference, and resolution of chiral derivatives. Polycyclic cage compounds are constructed from building units by linkages via covalent bonds, metal-coordination bonds, or hydrogen bonds. Large cage networks often include a wide range of guest species in their cavity to afford novel inclusion compounds. Topological isomers consisting of two or more macrocycles are formed by cyclization of preorganized species. Some complicated topological networks are constructed by self-assembly of simple building units.

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“…benzene-anthracene, naphthaleneanthracene, and anthracene-anthracene systems (ref. 6). Some isomeric anthracenophanes are expected due to the difference in stacking mode of two aromatic rings.…”

Section: Thermal Cycloaddition Anthracenophanesmentioning

confidence: 99%

“…A longer wavelength shift in electronic spectrum of [2.2]paracyclo-(9,10)anthracenophane 4 was ascribed to stronger interaction between the two Tr-systems, compared to that of the corresponding (l,4)isomer 3 (ref. 6). Synthesis of isomeric triple-layered anthracenophanes, 5 and 6, was undertaken by employing the Hofmann elimination method of the corresponding ammonium bases.…”

Section: Thermal Cycloaddition Anthracenophanesmentioning

confidence: 99%

Cycloaddition reactions of cyclophanes

Misumi¹

1987

Pure and Applied Chemistry

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-Unusual thermal and photochemical cycloaddition reactions of the aromatic rings in some cyclophanes are described. For example, the benzene in paracyclo(9,lO)anthracenophane functions as a dienophile in intramolecular DielsAlder reaction and tetracyanoethylene reacts easily with a triple-layered cyclophadiyne even at room temperature to give a 1:1 cycloadduct, suggesting a concerted process of three isolated Tr-systems. The formation of cage compounds by photoinduced cycloaddition and their reverse, thermal ring opening reactions are observed with syn[2.2](1,4)anthracenophane and dihetera quadruple-layered cyclophanes. A quantitative photodimerization of (9,1O)anthracenophadiyne and photoinduced bridge migration of multilayered metaparacyclophanes are discussed.

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Layered Compounds. LII. Syntheses of Eleven Anthracenophanes

Cited by 40 publications

References 15 publications

An unprecedented photodimerization of an anthraceno[2.2]paracyclophane

An unprecedented photodimerization of an anthraceno[2.2]paracyclophane

Three-Dimensional Aromatic Networks

Cycloaddition reactions of cyclophanes

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