CYCLOPHANES CONTAINING NITROGEN ATOMS IN THE BRIDGED CHAINS. PHOTOCHROMISM OF <i>N</i>,<i>N</i>′-BIS(ARYLSULFONYL)-2,11-DIAZA[3.3]PARACYCLO(9,10)ANTHRACENOPHANES1)

Usui, Masao; Nishiwaki, T.; Anda, Kinji; Hida, Mitsuhiko

doi:10.1246/cl.1984.1561

Cited by 13 publications

(12 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Das legt die Strukturen 4 und 4′ nahe (Schema ). Photocycloadditionen zwischen zwei Benzolringen10 oder zwischen einem Anthracen‐ und einem Benzolringsystem11 sind äußerst selten und bis dato nur intramolekular in einigen starren Strukturen beobachtet worden.…”

Section: Methodsunclassified

15. Österreichische Chemietage

2013

Nachr Chem

View full text Add to dashboard Cite

show abstract

Section: Methodsunclassified

15. Österreichische Chemietage

2013

Nachr Chem

View full text Add to dashboard Cite

show abstract

“…Octahedrane is the lowest member of the (CH) 2n polyhedrane hydrocarbon family (Figure 7). It is well known that a higher polyhedrane homologue, dodecahedrane [(CH) 20 ], has been independently synthesized by Paquette and co-workers 69 and Prinzbach and coworkers. 54a,b Octahedrane is known as one of the possible benzene dimers [(CH) 12 ] 70 and has been predicted to be the most-stable structure among them.…”

Section: Photoreactions Of the 211-diaza[3 2 ]Paracyclophane Systemmentioning

confidence: 99%

“…In contrast to the broad studies on such bridged chromophores, there have only been a few investigations into the photochemistry of cyclophanes or linked aromatics possessing nitrogen-containing bridges. 10,20 Since the carbon-nitrogen single bond is generally shorter than carbon-carbon, carbon-sulfur, or carbon-silicon s-bonds, 21 it is expected that cyclophanes possessing carbon-nitrogen bond(s) in their bridge chains will display more significant interactions between their aromatic nuclei than the corresponding cyclophanes with carbon-carbon, carbon-sulfur, or carbon-silicon bridges, thus enhancing their photoreactivity.…”

Section: Introductionmentioning

confidence: 99%

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

Okamoto¹,

Yamaji

Satake³

2008

Synlett

View full text Add to dashboard Cite

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.

show abstract

“…This finding points to structures 4 and 4' ' (Scheme 2). Photocycloadditions between two benzene rings [10] or between an anthracene and a benzene ring system [11] are extremely rare; up to now they were only observed in intramolecular reactions of a few rigid structures.…”

mentioning

confidence: 99%

The Unusual Photochemistry of Dendrimers with an Anthracene Core

Cao

Meier

2001

Angew. Chem. Int. Ed.

View full text Add to dashboard Cite

CYCLOPHANES CONTAINING NITROGEN ATOMS IN THE BRIDGED CHAINS. PHOTOCHROMISM OF N,N′-BIS(ARYLSULFONYL)-2,11-DIAZA[3.3]PARACYCLO(9,10)ANTHRACENOPHANES1)

Abstract: Diaza[3.3]paracyclo(9,10)anthracenophane derivatives were synthesized under the high dilution conditions. These cyclophanes showed reproducible photochromism both in solution and solid.

Cited by 13 publications

References 2 publications

15. Österreichische Chemietage

15. Österreichische Chemietage

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

The Unusual Photochemistry of Dendrimers with an Anthracene Core

Contact Info

Product

Resources

About

CYCLOPHANES CONTAINING NITROGEN ATOMS IN THE BRIDGED CHAINS. PHOTOCHROMISM OF N,N′-BIS(ARYLSULFONYL)-2,11-DIAZA[3.3]PARACYCLO(9,10)ANTHRACENOPHANES1)

Abstract: Diaza[3.3]paracyclo(9,10)anthracenophane derivatives were synthesized under the high dilution conditions. These cyclophanes showed reproducible photochromism both in solution and solid.

Cited by 13 publications

References 2 publications

15. Österreichische Chemietage

15. Österreichische Chemietage

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

The Unusual Photochemistry of Dendrimers with an Anthracene Core

Contact Info

Product

Resources

About

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