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Titolo:
CYCLOBIS(PARAQUAT-4,4'-BIPHENYLENE) - AN ORGANIC MOLECULAR SQUARE
Autore:
ASAKAWA M; ASHTON PR; MENZER S; RAYMO FM; STODDART JF; WHITE AJP; WILLIAMS DJ;
Indirizzi:
UNIV BIRMINGHAM,SCH CHEM,POB 363 BIRMINGHAM B15 2TT W MIDLANDS ENGLAND UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM LONDON SW7 2AY ENGLAND
Titolo Testata:
Chemistry
fascicolo: 7, volume: 2, anno: 1996,
pagine: 877 - 893
SICI:
0947-6539(1996)2:7<877:C-AOMS>2.0.ZU;2-Y
Fonte:
ISI
Lingua:
ENG
Soggetto:
CHARGE-TRANSFER COMPLEXES; BOND DIRECTED COCRYSTALLIZATION; HYDROGEN-BOND; SUPRAMOLECULAR CHEMISTRY; TRANSITION-METAL; SOLID-STATE; 2ND-SPHERE COORDINATION; CRYSTAL-STRUCTURE; PHOTOACTIVE )2>ROTAXANES; TRANSLATIONAL ISOMERISM;
Keywords:
CATENANES; 2ND-SPHERE COORDINATION; SELF-ASSEMBLY; TEMPLATE SYNTHESES; TOPOLOGICAL STEREOISOMERISM;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
145
Recensione:
Indirizzi per estratti:
Citazione:
M. Asakawa et al., "CYCLOBIS(PARAQUAT-4,4'-BIPHENYLENE) - AN ORGANIC MOLECULAR SQUARE", Chemistry, 2(7), 1996, pp. 877-893

Abstract

Template-directed syntheses of cycle bis(paraquat-4,4'-biphenylene) (1) - a molecular square - have been achieved by use of pi-electron-rich macrocyclic hydroquinone-based and acyclic ferrocene-based templates. In particular, the use of a polyether-disubstituted ferrocene derivative as a template permits synthesis of 1 (which is accessible only invery low yields without templates) on a preparative scale. Furthermore, the use of a macrocyclic hydroquinone-based polyether template incorporating an ester function in one polyether chain-an ''oriented'' macrocycle-affords a 1 : 1 mixture of two topologically stereoisomeric [3] catenanes. Ester hydrolysis of the pi-electron-rich macrocyclic components mechanically interlocked with 1 within the catenated structuresreleases the tetracationic cyclophane in quantitative yield as a result of the degradation of the [3]catenanes. The molecular square has been characterized by X-ray crystallography, FAB mass spectrometry, H-1 NMR and C-13 NMR spectroscopies, and elemental analysis. The binding properties of 1 and of the smaller cyclophane cyclobis(paraquat-p-phenylene) toward a series of pi-electron-rich guests have also been investigated with the above techniques and UV/VIS spectroscopy. The self-assembly of the resulting supramolecular complexes in solution and in thesolid state is driven mainly by pi-pi stacking interactions and hydrogen-bonding interactions, as well as by edge-to-face T-type interactions. In particular, the complexation of ferrocene or a ferrocene-based derivative within the cavity of 1 suggests the possibility of constructing functioning ferrocene-based molecular and supramolecular devices that can be controlled electrochemically in the form of catenanes, rotaxanes, and pseudorotaxanes.

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Documento generato il 26/01/20 alle ore 23:09:12