The highly stable 1,6-methanotetradehydro-[26]-, -[28]-, -[30]-, -[32]-, -[34]-, and -[38]-annulenes. Limiting ring size for dia- and para-tropicity

Ojima, J.; Fujita, Shin; Masumoto, Masayuki; Ejiri, Emiko; Kato, T.; Kuroda, Shigeyasu; Nozawa, Y.; Tatemitsu, Hitoshi

doi:10.1039/c39870000534

Cited by 8 publications

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“…There are three reported systems 3 a-f, 4 a-f, and 5 concerning the ring current effect of macrocyclic annulenes. [13][14][15] Interestingly, [34]annulene 4 c is aromatic, whereas [38]annulene 4 d does not show any aromatic ring current effects. In contrast, [28]annulene 4 e is paratropic, whereas [32]annulene 4 f is atropic.…”

Section: Annulenes and Dehydroannulenesmentioning

confidence: 95%

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Conjugated Macrocycles: Concepts and Applications

2011

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One of the most important objectives in materials, chemical, and physical sciences is the creation of large conjugated macrocycles with well-defined shapes, since such molecules are not only theoretically and experimentally interesting but also have potential applications in nanotechnology. Fully unsaturated macrocycles are regarded as models for infinitely conjugated π systems with inner cavities, and exhibit unusual optical and magnetic behavior. Macrocycles have interior and exterior sites, and site-specific substitution at both or either site can afford attractive structures, such as 1D, 2D, and 3D supramolecular nanostructures. These nanostructures could be controlled through the use of π-extended large macrocycles by a bottom-up strategy. Numerous shape-persistent π-conjugated macrocycles have been synthesized, but only a few are on the nanoscale. This Review focuses on nanosized π-conjugated macrocycles (>1 nm diameter) and giant macrocycles (>2 nm diameter), and summarizes their syntheses and properties.

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Section: Annulenes and Dehydroannulenesmentioning

confidence: 95%

“…In contrast, [28]annulene 4 e is paratropic, whereas [32]annulene 4 f is atropic. [14] Furthermore, the D 6h -symmetric [30]annulene 5 shows a large diatropic ring current, despite its stability. [15] Quite recently, [36]annulene derivative 7 composed of anthrylene, phenylene, and ethylene units was reported.…”

Section: Annulenes and Dehydroannulenesmentioning

confidence: 98%

Conjugated Macrocycles: Concepts and Applications

2011

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“…Mit Blick auf die Ringstromeffekte makrocyclischer Annulene wurden die drei Systeme 3 a-f, 4 a-f und 5 beschrieben. [13][14][15] Interessanterweise ist das [34]Annulen 4 c aromatisch, wohingegen das [38]Annulen 4 d keinerlei aromatische Ringstromeffekte aufweist. Das [28]Annulen 4 e ist paratrop, das [32]Annulen 4 f atrop.…”

Section: Annulene Und Dehydroannuleneunclassified

“…Das [28]Annulen 4 e ist paratrop, das [32]Annulen 4 f atrop. [14] Das D 6h -symmetrische [30]Annulen 5 zeigt trotz seiner Stabilität einen starken diatropen Ringstrom. [15] Erst vor kurzem wurde das [36]Annulen-Derivat 7 beschrieben, das aus Anthrylen-, Phenylen-und Ethyleneinheiten aufgebaut ist.…”

Section: Annulene Und Dehydroannuleneunclassified

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Konjugierte Makrocyclen: Konzepte und Anwendungen

2011

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Eines der wichtigsten Ziele in den Materialwissenschaften, der Chemie und der Physik ist die Herstellung von großen konjugierten Makrocyclen genau definierter Form, da solche Moleküle nicht nur theoretisch und experimentell interessant sind, sondern auch potenzielle Anwendungen in der Nanotechnologie haben. Vollständig ungesättigte Makrocyclen werden als Modelle für vollständig konjugierte π‐Systeme mit Hohlräumen herangezogen. Solche konjugierten π‐Systeme zeigen aufgrund ihrer cyclischen Konjugation ein ungewöhnliches optisches und magnetisches Verhalten. Makrocyclen haben nach innen und nach außen gerichtete Bindungsstellen, und eine positionsspezifische Substitution an beiden oder nur einer der beiden Bindungsstellen kann attraktive Strukturen zugänglich machen. Von besonderer Bedeutung sind ein‐, zwei‐ und dreidimensionale supramolekulare Nanostrukturen. Um die Bildung dieser Strukturen kontrollieren zu können, bietet sich die Bottom‐Up‐Synthese ausgehend von π‐expandierten Makrocyclen an. Zahlreiche formstabile π‐konjugierte Makrocyclen wurden synthetisiert, davon aber nur eine begrenzte Zahl an nanoskaligen Vertretern. In diesem Aufsatz konzentrieren wir uns auf nanometergroße π‐konjugierte Makrocyclen (>1 nm Durchmesser) sowie Riesenmakrocyclen (>2 nm Durchmesser) und fassen deren Synthesen und Eigenschaften zusammen.

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Cacoub¹,

Frémeaux‐Bacchi²

2002

Arthritis & Rheumatism

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One of the most important objectives in materials, chemical, and physical sciences is the creation of large conjugated macrocycles with well‐defined shapes, since such molecules are not only theoretically and experimentally interesting but also have potential applications in nanotechnology. Fully unsaturated macrocycles are regarded as models for infinitely conjugated π systems with inner cavities, and exhibit unusual optical and magnetic behavior. Macrocycles have interior and exterior sites, and site‐specific substitution at both or either site can afford attractive structures, such as 1D, 2D, and 3D supramolecular nanostructures. These nanostructures could be controlled through the use of π‐extended large macrocycles by a bottom‐up strategy. Numerous shape‐persistent π‐conjugated macrocycles have been synthesized, but only a few are on the nanoscale. This Review focuses on nanosized π‐conjugated macrocycles (>1 nm diameter) and giant macrocycles (>2 nm diameter), and summarizes their syntheses and properties.

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The highly stable 1,6-methanotetradehydro-[26]-, -[28]-, -[30]-, -[32]-, -[34]-, and -[38]-annulenes. Limiting ring size for dia- and para-tropicity

Cited by 8 publications

References 0 publications

Conjugated Macrocycles: Concepts and Applications

Conjugated Macrocycles: Concepts and Applications

Konjugierte Makrocyclen: Konzepte und Anwendungen

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