[2.2.2.2.2.2](1,2,3,4,5,6)Cyclophane: superphane

Sekine, Yasuo; BROWN, M. F.; Boekelheide, V.

doi:10.1021/ja00505a053

Cited by 115 publications

(52 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Only the combined consideration of transanular interaction and through-bond interaction accounts satisfactorily for the observed ionization potentials [14] and for the longest wavelength absorption in the UV spectra in the series of [2,] (i) Both phanes 1 and 2 show with 262.4 pm for 1 [17] and with 270 pm (mean value) for 2 [18] the smallest transanular distance which can be realized in a hydrocarbon phane. This should result in a stronger transanular T-electron interaction and in a greater importance of the symmetric charge transfer terms.…”

Section: Inandmmmentioning

confidence: 98%

Electronic spectra and triplet state properties of superphane

Schweitzer¹,

Hausser²,

Vogler³

et al. 1986

Chemical Physics

Self Cite

View full text Add to dashboard Cite

ne emission and the zero-field splitting parameters D and E of the superphane 1 and the [2,](1,2,3,4,5)-cyclophane 2 are investigated. The large number of six and five metbyiene bridges, respectively, leads to a more rigid molecular frame and to a smaller transanular distance as compared to other ~2,2~~oph~~. The experimental results exhibit characteristic features which are due to these unusual properties; they are discussed and compared with ~-empi~~ a-electron cakuIations.

show abstract

Section: Inandmmmentioning

confidence: 98%

Electronic spectra and triplet state properties of superphane

Schweitzer¹,

Hausser²,

Vogler³

et al. 1986

Chemical Physics

Self Cite

View full text Add to dashboard Cite

show abstract

“…Diese cyclische Diketoneinheit ist bereits in früheren Arbeiten [6,18] erfolgreich als Syntheseäquivalent für Alkinylgruppen eingesetzt worden, die daraus durch thermische oder photochemische CO-Abspaltung freigesetzt werden können. Die schrittweise Decarbonylierung von 12 sollte schlieûlich zum Cyclophin 13 (C 60 H 6 [21] und Superferrocenophan 16 [22] als lange etablierten strukturellen Vorstufen ist es wahrscheinlich, daû schon bald über die geglückte Herstellung von ¹Superphinª 17, einem acetylenischen Isomer des Buckminsterfullerens, oder gar von einem ¹Supermetallophinª berichtet werden kann.…”

Section: Rüdiger Faust*unclassified

Explosionen als Synthesemethode? Cycloalkine als Vorstufen für Fullerene, Buckyröhren und Buckyzwiebeln

Faust¹

1998

Angewandte Chemie

View full text Add to dashboard Cite

Eine provokative Frage wirft der Titel auf – Explosionen werden sich längerfristig wohl nicht als allgemeine Synthesemethode durchsetzen, doch erbrachte die explosionsartige Zersetzung einiger gespannter Dehydrobenzoannulene beim Erhitzen interessante Ergebnisse; unter anderem entstanden strukturierte, Fulleren‐artige Kohlenstoffpartikel. Die spektakuläre Thermochemie dieser Cycloalkine gibt Anlaß zur Hoffnung, daß acetylenische Cyclophane wie 1 nach Anregung zu Kohlenstoffkugeln koaleszieren können. Die vielversprechenden Ergebnisse, die auf diesem Gebiet erzielt worden sind, werden in diesem Beitrag vorgestellt.

show abstract

“…In this work, the spatial structure of hypothetical hexahydrosuperphane 11 is studied together with its IR spectra and NMR chemical shifts using quantum chemistry calculations. The data calculated for 11 are compared with the corresponding experimental results for superphane 12, [15][16][17][18] obtained by the Boekelheide group, [19] and perhydrogenated [ …”

Section: Introductionmentioning

confidence: 99%

Planarization of the Cyclohexane Ring by Its Incorporation Into a Cyclophane Cage: Hexahydrosuperphane

Dodziuk

Ostrowski

2006

Eur J Org Chem

View full text Add to dashboard Cite

Calculations at the HF/6‐311G(d,p), DFT B3LYP/6‐311G(d,p), and MP2/6‐311G(d,p) levels show that the hypothetical molecule hexahydrosuperphane should have a planar saturated ring imposed by its incorporation into a cyclophane. The calculated NMR chemical shifts are compared with the experimental literature data for a few compounds with similar structure fragments. The calculated vibrational frequencies and the analysis of possible decomposition routes of the title molecule indicate that the molecule should be stable. Thus, it represents a plausible synthetic target. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

show abstract

[2.2.2.2.2.2](1,2,3,4,5,6)Cyclophane: superphane

Cited by 115 publications

References 2 publications

Electronic spectra and triplet state properties of superphane

Electronic spectra and triplet state properties of superphane

Explosionen als Synthesemethode? Cycloalkine als Vorstufen für Fullerene, Buckyröhren und Buckyzwiebeln

Planarization of the Cyclohexane Ring by Its Incorporation Into a Cyclophane Cage: Hexahydrosuperphane

Contact Info

Product

Resources

About