Macro Rings. VII. The Spectral Consequences of Bringing Two Benzene Rings Face to Face<sup>1</sup>

Cram, Donald J.; Allinger, Norman L.; Steinberg, H.

doi:10.1021/ja01652a081

Cited by 204 publications

(64 citation statements)

References 1 publication

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“…It is found that the first vibrational band is considerably shifted to lower energy. This change is reminiscent to that found in the absorption spectra of (n.n)paracyclophanes [91].…”

Section: 53supporting

confidence: 55%

Carbon‐rich Cycles with Two and More 1,3‐Butadiyne Units – Syntheses, Structures and Reactivities

Gleiter

Werz²

2006

Carbon‐Rich Compounds

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“…It is found that the first vibrational band is considerably shifted to lower energy. This change is reminiscent to that found in the absorption spectra of (n.n)paracyclophanes [91].…”

Section: 53supporting

confidence: 55%

Carbon‐rich Cycles with Two and More 1,3‐Butadiyne Units – Syntheses, Structures and Reactivities

Gleiter

Werz²

2006

Carbon‐Rich Compounds

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“…The ligand-ligand interaction of MgCp 2 which causes the red shift of the absorption to 240 nm finds its counterpart in the transannular interaction of [2.2]paracyclophane [3,4]. In this case the ethane bridges enforce a rather strong arene-arene coupling which shifts the longest-wavelength absorption to approximately 315 nm [3,4,17].…”

Section: Resultsmentioning

confidence: 99%

Optical properties of bis(cyclopentadienyl)magnesium: excimer-type luminescence of the bis(cyclopentadienyl) ligand frame

Kunkely

Vogler

2004

Journal of Organometallic Chemistry

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“…18,19 The reactions of such cyclophanes have also attracted interest because the incorporated benzene pair display reactions that are significantly different from those of the nonbridged benzene chromophores upon stimulation, i.e. by light.…”

Section: General Remarks On the Photoreactions Of Cyclophanes Containmentioning

confidence: 99%

Photochemistry of Nitrogen-Bridged Cyclophanes: 2,11-Diaza[3₂]anthracenoparacyclophane and 2,11-Diaza[3₂]paracyclophane Systems

Okamoto¹,

Yamaji

Satake³

2008

Synlett

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This account provides an overview of the photochemical properties of cyclophanes possessing nitrogen atoms in the bridge chains, namely 2,11-diaza[3 2 ]anthracenoparacyclophane and 2,11-diaza[3 2 ]paracyclophane systems. Although the photoreactions of aromatic molecules that are bound by a linker or fixed in a cyclophane structure have been widely investigated, much less attention has been paid to the photochemistry of aromatic rings incorporated in a nitrogen-bridged cyclophane. During the course of our work on the photoreactions of cyclophanes possessing nitrogen atoms in their bridge chains, the nitrogen-bridged cyclophanes were found to display photoproperties significantly different from those of the nonbridged aromatic chromophores or the corresponding carbonbridged cyclophane analogues. The 2,11-diaza[3 2 ]anthracenoparacyclophane system displayed an efficient photochemical cycloaddition-adiabatic cycloreversion cycle in the excited singlet state, while in the triplet state, the photoisomer underwent a novel rearrangement and adiabatic cycloreversion. Upon photolysis of the 2,11-diaza[3 2 ]paracyclophane system, an octahedrane cage was formed. This is the first reported octahedrane formation to occur by the photochemical dimerization of benzene. Thus, the title cyclophane systems display a variety of photoprocesses involving cycloaddition, adiabatic cycloreversion accompanied by photoinduced chemiluminescence, novel rearrangements, and previously unknown benzene dimerization.

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Macro Rings. VII. The Spectral Consequences of Bringing Two Benzene Rings Face to Face¹

Cited by 204 publications

References 1 publication

Carbon‐rich Cycles with Two and More 1,3‐Butadiyne Units – Syntheses, Structures and Reactivities

Carbon‐rich Cycles with Two and More 1,3‐Butadiyne Units – Syntheses, Structures and Reactivities

Optical properties of bis(cyclopentadienyl)magnesium: excimer-type luminescence of the bis(cyclopentadienyl) ligand frame

Photochemistry of Nitrogen-Bridged Cyclophanes: 2,11-Diaza[3₂]anthracenoparacyclophane and 2,11-Diaza[3₂]paracyclophane Systems

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Macro Rings. VII. The Spectral Consequences of Bringing Two Benzene Rings Face to Face1

Cited by 204 publications

References 1 publication

Carbon‐rich Cycles with Two and More 1,3‐Butadiyne Units – Syntheses, Structures and Reactivities

Carbon‐rich Cycles with Two and More 1,3‐Butadiyne Units – Syntheses, Structures and Reactivities

Optical properties of bis(cyclopentadienyl)magnesium: excimer-type luminescence of the bis(cyclopentadienyl) ligand frame

Photochemistry of Nitrogen-Bridged Cyclophanes: 2,11-Diaza[32]anthracenoparacyclophane and 2,11-Diaza[32]paracyclophane Systems

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Macro Rings. VII. The Spectral Consequences of Bringing Two Benzene Rings Face to Face¹

Photochemistry of Nitrogen-Bridged Cyclophanes: 2,11-Diaza[3₂]anthracenoparacyclophane and 2,11-Diaza[3₂]paracyclophane Systems